Abstract
Over the past two centuries, fused N-heterocyclic compounds are extensively utilized as valuable entities for the expansion of pharmacological significant agents and deliberated as one of the advantaged scaffolds. Among the numerous fused N-heterocyclic compounds, cinnoline, quinoxalines and quinazolines are significant pharmacological agents, and a noteworthy amount of study has been conducted regarding this type of compounds. In medicinal chemistry, these N-heterocyclic compounds have broad range of biological properties and used as synthetic intermediates, potential drug candidates and chemical probes. Since they are indispensable moieties to treat infectious diseases, in the past years, there is a surge in the significance of designing innovative cinnoline, quinoxalines and quinazolines derivatives, sightseeing auspicious methods to access these moieties, examining their different properties and potential applications. The aim of this chapter is to highpoint the topical studies made by chemist on numerous biological activities and synthetic methods of cinnoline, quinoxalines and quinazolines via sustainable synthetic approaches described in the literature. It would buoyantly be useful for the researchers who have fascinates in evolving innovative therapeutic agents and associated valuable chemical probes.
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9.1 Introduction
Heterocycles engage a middle arrangement in synthetic organic chemistry. Over the past two centuries, heterocyclic chemistry has been soundly established due to the agricultural, pharmaceutical and industrial importance of the majority of organic-based value-added chemicals. Heterocyclic entities play an essential position in Natural systems and show a noteworthy involvement in maintaining livelihood (Brahmachari 2015). They are extensively scattered in “Universe” which is crucial for existence such as oxygen transporting pigment “hemoglobin,” photosynthetic pigment “chlorophyll,” plant alkaloids (e.g., Strychnine, Flavones), vitamins (e.g., vitamin B6, vitamin E), enzymes, polysaccharides, anthocyanins, energy carrier (e.g., ATP, ADP), neurotransmitter (e.g., Serotonin, Histamine) and nucleic acid (DNA and RNA) (Shalini et al. 2010; Keri et al. 2014; Afzal et al. 2015; Shinde and Haghi 2020; Hussaini et al. 2019). Furthermore, numerous amino acids, alkaloids (e.g., nicotine and caffeine), carbohydrates, hormones, pheromones, antibiotics, antioxidants, flavorings and perfumes, etc. are also value-added heterocyclic compounds that are important for our life (Berger 2007; Ramsewak et al. 1999; Padwa et al. 1992; Festa et al. 2019; Ameta et al 2014; Lambat et al. (2020); Liu and Fu (2012); Dandia et al. 2011, 2012, 2013a, 2014, 2020a; b) (Fig. 9.1).
Heterocyclic materials at the interface of chemistry and biology
9.1.1 N-Heterocyclic Compounds
As life has developed in universe over last centuries, nature has expanded an assortment of valuable heterocyclic compounds that provide as chemical couriers that activate biological feedbacks and regulate biological course of actions, more commonly. N-Heterocyclic compounds have become an imperative contributor of everyday life during last the century and it plays a major role in our environment (Verma 2020). The chemistry of “N-Heterocycles” attracts particular concentration in science basically due to its enormous significance to our everyday life. N-Heterocyclic compounds have diverse uses such as in life saving drugs, optoelectronics, flavoring agents, polymers, herbicides, preservatives, anticorrosive agent, light-emitting diode, fragrances, fabric whiteners, fertilizers, conductivity-based sensors, pesticides, agrochemicals and modifier for rockets propellant fuels (Dandia et al. 2012, 2013c, 2015, 2016, 2017a, b, 2018a, 2019a, 2020a, b, c, 2021a, b, c).
Owing to their marvelous impact of N-heterocyclic compounds in our humanity, there are constant demands to decrease unpreserved resources and expenses to have less disadvantageous impact to the atmosphere. The fused N-heterocyclic compounds have an immense significance in therapeutic chemistry (Aher et al. 2014; Mermer et al. 2021; Bhardwaj et al. 2021). One of the most imperative fused scaffolds in medicinal chemistry is cinnolines, quinoxalines and quinazolines (Scheme 9.1).
Isomeric form of the fused N-heterocyclic compounds containing two N-atoms in the benzene ring
They are well-known heterocycles for their extensive pharmacological properties counting anticancer, anticonvulsant, anti-allergic, anti-inflammatory, antidiabetic, antimalarial, antibacterial, antitumor, antitubercular, antihypertensive, as anti-hypertensive, antihistamine and antihypertensive (Taek et al. 2017).
The N-heterocyclic fused ring has drained an enormous deliberation because of their prolonged applications in field of therapeutic chemistry. This chapter assembles the modern work on fused 6-membered N-heterocyclic scaffolds with two N-atoms like quinoxalines, cinnoline and quinazolines reported in literature by researchers (Keneford et al. 1950; Mathew et al. 2017; Mamedov 2016; Chandra et al. 2014). These N-heterocyclic compounds are manufactured from combination of pyrimidine and benzene ring. One benzene ring contains two N-atoms. On the basis of position of the two nitrogen atoms these fused N-heterocyclic compounds are named as cinnoline, quinoxalines and quinazolines (Fig. 9.2).
Structure of fused N-heterocyclic compounds and its isomers cinnoline, quinoxalines and quinazolines
9.2 Cinnoline
9.2.1 Introduction
Cinnoline is an organic N-heterocyclic compound having molecular formula C8H6N2. Cinnoline (1,2-benzodiazine) has fascinated a great covenant of attention owing to their friendship with a variety of pharmaceutical and biological properties (Lewgowd and Stanczak 2007; Abdelrazek et al. 2006; Somei and Ura 1978). It is a fused N-heterocyclic compound in which two N-atoms are present at 1,2 position (benzene and pyrimidine ring). It is an isomeric form of quinoline or isoquinoline and also with phthalazine.
As a outcome of widespread range of biological significance’s for example anti-inflammatory, analgesic, anxiolytic, antitumor, antimalarial, antifungal and antibacterial activities of cinnoline (1,2-benzodiazine) derivatives, enormous endeavor has been made to construct these bioactive molecules (Fig. 9.3). For that reason, construction of these biologically active N-heterocyclic moieties has increased enormous significance in organic synthesis. The plenty implication of Cinnoline (1,2-benzodiazine) derivatives have influence them to meet via the development of various organic transformations (Alvarado et al. 2006; Tian et al. 2021; Rinderspacher et al. 2021; Kandeel et al. 2018; Bommagani et al. 2020). To date many procedures have been described to access these scaffolds.
General structures of cinnoline-based biological active compounds
9.2.2 Various Approaches for the Preparation of Cinnolines
An exceedingly proficient microwave-assisted method to access bioactive molecules of cinnoline derivatives by the reaction of 4-Alkylpyridazine and nitrostyrene in dioxane/piperidine at 100 °C was presented by Hameed et al. (2017) (Scheme 9.2).
Microwave-assisted method to access bioactive molecules of cinnoline derivatives
Feng et al. (Li et al. 2021a) designed a straightforward and palladium-catalyzed sustainable pathway to afford biologically important cinnoline derivatives via one-pot dual C–H activation strategy in AcOH at 80 °C (Scheme 9.3).
Palladium-catalyzed sustainable pathway to afford biologically important cinnoline derivatives
Mekheimer et al. (Nazmy et al. 2020) described a microwave-induced reaction in dioxane/piperidine to generate densely functionalized cinnolines derivatives at 100 °C. The synthesized cinnolines derivatives show in vitro anticancer biological activity through apoptosis generation (Scheme 9.4).
Microwave-induced reaction in dioxane/piperidine to generate densely functionalized cinnolines derivatives
An competent and green Neber Bossel preparation of several cinnolines from diazotization of (2-aminophenyl)-hydroxyacetate under acidic conditions at 0 °C was introduced by Henry et al. (1960) The reaction was followed by intramolecular condensation and aromatization (Scheme 9.5).
Neber Bossel synthesis of several cinnoline derivatives
Barber et al. (1961) have been demonstrated catalytic behavior of TiCl4 to afford a library of biologically relevant compounds cinnolines by intramolecular cyclization of phenylhydrazone-linked acid chloride under Friedel–Crafts condition (Scheme 9.6).
TiCl4 catalyzed production of biologically relevant scaffolds
A proficient pathway for the production biologically important cinnolines utilizing PPA catalyst at 100–120 °C was explained by Mubarak and co-workers (Awad et al. 2012). The cinnoline is formed through hydrazone intermediate. The author observed that the formed cinnoline derivatives show anticancer and antibacterial activity (Scheme 9.7).
Production biologically important cinnolines utilizing PPA catalyst
Cu(I) catalyzed production of various functionalized cinnolines derivatives through tandem C–N bond forming reaction using K2CO3 and DMEDA in dioxane at 90 °C was described by Willis and co-workers (Ball et al. 2012). The reported method is based on diazotization chemistry (Scheme 9.8).
Cu(I) catalyzed production of various functionalized cinnolines derivatives
Zhang et al. (2012) used Cu(II) as green catalyst for the aerobic dehydrogenative cyclization of hydrazine to afford pharmacologically important cinnoline derivatives followed by the Csp3-H oxidation, cyclization and aromatization sequence in DMF under air atmosphere at 110 °C (Scheme 9.9).
Cu(II) induced aerobic dehydrogenative cyclization of hydrazine to afford pharmacologically important cinnoline derivatives
A proficient formal [2 + 2 + 2] cycloaddition of arynes, tosylhydrazine and α-bromoketones to access cinnoline derivatives catalyzed by CsF in CH3CN at 90 °C was developed by Shu co-workers (Shu et al. 2016). In this transition-metal-free reaction, two C-N bond and one C–C bond are formed via one-pot succession (Scheme 9.10).
[2 + 2 + 2] cycloaddition of arynes, tosylhydrazine and α- bromoketones to access cinnolines catalyzed by CsF
Au(I)-induced hydroarylation of N-propargyl-N’-arylhydrazines has been successfully applied to generate 4-exo-methylene-1,2-dihydrocinnoline derivatives via hydroarylation process in refluxing nitromethane under catalytic acidic conditions were reported by Gagosz et al. (2011) In this reaction [XPhosAu(NCCH3)SbF6] is used as Au complex (Scheme 9.11).
Au(I)-induced synthesis of cinnolines
9.3 Quinazoline
9.3.1 Introduction
Quinazoline is well-known N-containing heterocyclic compounds for their extensive pharmacological properties including anticancer, antifungal, antibacterial, antiulcer, anticonvulsant, antiinflammatory, antidiabetic, antimalarial, antitumor, antitubercular, antihypertensive, antihistamine and antihypertensive (Wang et al. 2013; Kuneš et al. 2000; Ravez et al. 2015; Alafeefy et al. 2010; Marzaro et al. 2012). They are also found in numerous natural products like L-vasicinone, ispinesib, luotonin E, circumdatin F and sclerotingenin and pharmaceutical drugs. Numerous quinazolines are presently in utilized for therapeutic motive owing to their superior pharmaceutical proficiency (Abuelizz et al. 2017; El-Azab et al. 2010).
Quinazolinone alkaloids (derivative of quinazoline) are widely present in nature. Quinazolinones have also been provided as constructive synthetic intermediates. Furthermore, these quinazolinone motifs are of attention as COX-2 inhibitors, herbicidal agents, anti-allergic, antipsychotic, melatonin receptor MT1 and agonists (Ahmad et al. 2017; Rehuman et al. 2021; Li et al. 2021b; Zheng et al. 2020; Selvam et al. 2011) (Fig. 9.4).
Biological activities of quinazoline-based compounds
Owing to their remarkable properties, traditionally various synthetic approaches have been the subject of several publications for the production of derivatives of quinazoline.
9.3.2 Various Approaches for the Preparation of quinazolines
To date many procedures have been developed to prepare these compounds.
t-butylhydroperoxide is used as a competent and efficient catalyst by Asif et al. (2014) to generate quinazoline derivatives from aminobenzophenones and benzylamines in acetonitrile (Scheme 9.12).
Ceric ammonium nitrate-t-butylhydroperoxideis catalyzed synthesis of quinazoline derivatives
Pd is used as a competent catalyst by Wang and co-workers (Wang et al. 2011) to synthesize 4-aminoquinazoline derivatives from isonitriles and N-aryl amidines in toluene. This reaction takes place via intramolecular C(sp2)-H amidination (Scheme 9.13).
Pd(OAc)2 catalyzed synthesis of 4-aminoquinazoline derivatives
An exceedingly proficient microwave-promoted synthesis of bioactive molecules of quinazoline derivatives from o-phenyl oximes and aldehydes was presented by Portela-Cubillo and co-workers (Portela-Cubillo et al. 2009). For this microwave-promoted reactions, ZnCl2 is used as efficient catalyst with PF4 (Scheme 9.14).
Microwave-promoted synthesis of bioactive molecules of quinazoline derivatives
Ferrini et al. (2007) illustrated new microwave-induced cyclization reactions to afford quinazolines through Fries rearrangement reactions of anilides catalyzed by ammonium formate. For this Fries rearrangement reaction, salicylamides are formed by the acylation of o-aminoacyl benzene derivatives (Scheme 9.15).
Microwave-induced cyclization reactions to afford quinazolines through fries rearrangement reactions of anilides catalyzed by ammonium formate
Ligand-free copper has been successfully used as cheap and willingly accessible catalyst to generate 2-phenylquinazolines (quinazoline derivatives) from 2-bromophenyl methyl amines and amindes was described by Zhang et al. (2010). In this method, K2CO3 is used as a mild base (Scheme 9.16).
Production of quinazolines derivatives using ligand-free copper catalyst
Dandia and co-workers (2019b) envisaged a commercially available Cu(I)-catalyzed novel flexible strategy for selective production of quinazolinones utilizing smoothly accessible anthranilonitrile and benzyl bromides. This reaction is complete through N-benzylation/CSp3-H oxidation/CN hydrolysis/cyclization sequence (Scheme 9.17).
Cu(I)-catalyzed novel flexible strategy for selective production of 2-aryl-quinazolin-4(3H)-ones derivatives
Dandia et al. (2018b) designed a new regioselective water-assisted strategy to access substituted quinazolinones from o-aminobenzamides with benzyl alcohols catalyzed by NaCl under microwave irradiation. In this approach, NaCl plays a deceive role for the C–N bond formation through “kosmotropes perturbation” (Scheme 9.18).
Regioselective water-assisted strategy to access quinazolinones catalyzed by NaCl
A novel and environmental friendly visible-light photoredox procedure to access quinazolinones in the presence of Cu decked ZnS nano-photocatalyst in CH3CN was reported by Dandia et al. (2020d). This reaction completed through amide intermediate (Scheme 9.19).
Visible-light photoredox procedure to access quinazolinones using Cu decked ZnS nano-photocatalyst
Peng et al. (2018) reported a convenient Pd-catalyzed carbonylative cyclization reaction to give 2,3-disubstituted quinazolinones derivatives utilizing Mo metal containing carbonyl complex as a reductant and a CO supplier (Scheme 9.20).
Pd-catalyzed carbonylative cyclization reaction to give 2,3-disubstituted quinazolinones
Ding et al. (Ren et al. 2018) demonstrated one-pot Pd(PPh3)4-initiated cross-coupling of 2-azidobenzamides and isocyanides to prepare biological active quinazolinones derivatives in DMF at room temperature (Scheme 9.21).
Pd(PPh3)4-initiated cross-coupling of 2-azidobenzamides and isocyanides to prepare biological active quinazolinones derivatives
Trifluoroacetic acid (TFA) has been successfully used as cheap and willingly accessible CF3 source to generate trifluoromethyl substituted quinazolinones by narrative and sensible chronological cascade pathway was introduced by Almeida and co-workers (2018) (Scheme 9.22).
Trifluoroacetic acid (TFA) catalyzed synthesis of quinazolinones
Huang et al. (Lin et al. 2019) developed an environmentally benign electrochemical process to afford substituted 2-aryl-quinazolinones derivatives through cascade cyclization of o-aminobenzamides with alcohols utilizing manganese(II) sulfate as a catalyst in CH3CN/H2O medium (Scheme 9.23).
Electrochemical process to afford substituted 2-aryl-quinazolinones derivatives
Salehi et al. (2005) accomplished a versatile way for the production of disubstituted quinazolinones by the reaction of commercially available reactants utilizing silica sulfuric acid at 80 °C temperature (Scheme 9.24).
Production of disubstituted quinazolinones utilizing silica sulfuric acid
Alper et al. (Zheng et al. 2008) demonstrated Pd(OAc)2/PPh3/CO-catalyzed cyclo-carbonylation of iodoanilines and acid chlorides to generate a series of quinazolinones proceed by in situ construction of an amidine (Scheme 9.25).
Pd(OAc)2/PPh3/CO-catalyzed synthesis of a series of quinazolinones
Lanthanide triflate [Yb(OTf)3] catalyzed production of pharmaceutical vital quinazolinones from 2-aminobenzoic acid, ortho-esters and amine was developed by Wang and co-workers (Wang et al. 2003) (Scheme 9.26).
Lanthanide triflate [Yb(OTf)3] catalyzed production of pharmaceutical vital quinazolinones
A broad and proficient process to synthesized a variety of quinazolinones from the condensation of aldehydes and anthranilamide catalyzed by the complex of Ir metal in aqueous medium was developed by Feng co-workers (Li et al. 2015) (Scheme 9.27).
Synthesis of quinazolinones in the presence of the complex of Ir metal
[Cu(Py)4(OTf)2] is found as an competent catalyst by Kapdi et al. (Gholap et al. 2017) to afford substituted quinazolinones derivatives through one-pot sequential way (Scheme 9.28).
[Cu(Py)4(OTf)2] catalyzed synthesis of substituted quinazolinones derivatives
[Cp*RhCl2] is found as competent catalyst by Xiong et al. (2018) to afford substituted quinazolinones derivatives through one-pot successive regioselective ortho-C–H amidation and cyclization of N-methoxybenzamide and dioxazolones under nitrogen atmosphere. In this reaction AgSbF6 is used as acid catalyst (Scheme 9.29).
[Cp*RhCl2] catalyzed synthesis of substituted quinazolinones derivatives
Bi-SO3H-functionalized ionic liquids (ILs) provoked aerobic oxidation approach to afford quinazolinones via solvation-induced proton transfer under air atmosphere described by Yu and co-workers (Yu et al. 2017) (Scheme 9.30).
Bi-SO3H-functionalized ionic liquids (ILs) provoked aerobic oxidation approach to afford quinazolinones
9.4 Quinoxaline
9.4.1 Introduction
Quinoxaline is isomeric form of quinoline or isoquinoline, phthalazine, cinnoline and also with phthalazine. It is also called a benzopyrazine. Quinoxalines are well-known fused N-containing heterocyclic compounds for their extensive pharmacological properties including anticancer, anticonvulsant, antineoplastic, antitubercular, antiamoebic, anti-HIV agent, antidepressant, antibacterial, antifungal, antimalarial, anti-inflammatory, antileishmanial, herbicidal, antiprotozoal, fungicidal, insecticidal, antioxidant and anti-ebola activities (Ahmed et al. 2018; Loughran et al. 2016; Ibrahim et al. 2017; Achutha et al. 2013; Carta et al. 2001; Shekhar et al. 2014; Ali et al. 2017; Corona et al. 2009).
Quinoxaline derivatives also exist in many natural compounds, for example vitamin B2, izumiphenazines A-C, cyclic peptide triostin A, hunanamycin A (Zhang et al. 2014; Abdelfattah et al. 2010; Henriques et al. 2010; Shingare et al. 2013; Hu et al. 2013; Refat et al. 2011) and DNA cleavage agents and functional materials (Dandia et al. 2012, 2013b, 2015, 2016, 2017a, 2020b, 2021a; b) (Aher et al. 2014; Mermer et al. 2021; Bhardwaj et al. 2021; Taek et al. 2017; Keneford et al. 1950; Mathew et al. 2017; Mamedov 2016). They are also important in the fields of technology for example chemical switches, cavitands, fluorescent dying agents, semiconductors and electroluminescent materials (Jaung 2006; Zhang et al. 2008; Thomas et al. 2005; Crossley and Johnston 2002; Dailey et al. 2001; Katoh et al. 2000; Sessler et al. 2002) (Fig. 9.5).
Biological activities of quinoxaline-based compounds
9.4.2 Various Approaches for the Preparation of Quinoxalines
To date many procedures have been developed to prepare these compounds.
Kundu and co-workers (Shee et al. 2020) described a straightforward and proficient NiBr2/1,10-phenanthroline system-promoted approach to generate quinoxalines using cesium carbonate at 150 °C. The used catalytic system is reusable for the next seventh cycle (dehydrogenative coupling reaction) (Scheme 9.31).
NiBr2/1,10-phenanthroline system-promoted approach to generate a series of quinoxalines
Alumina-supported heteropolyoxometalates (AlMoVP) has been successfully used as cheap and reusable catalyst to generate a series of quinoxalines from 1,2-dicarbonyls and 1,2-diamines at 25 °C was introduced by Romanelli and co-workers (Ruiz et al. 2012) (Scheme 9.32).
Alumina-supported heteropolyoxometalates (AlMoVP) catalyzed synthesis of a series of quinoxalines
An earth-abundant manganese(I) complex (Mn(CO)5Br) is demonstrated to be a competent catalyst for the preparation of functionalized quinoxalines and quinazolines by the dehydrogenative annulation reaction described by Balaraman et al. (Mondal et al. 2020). In this dehydrogenative annulation reaction, only H2O and H2 is formed as side product (Scheme 9.33).
Manganese(I) complex (Mn(CO)5Br) is used as catalyst for the preparation of functionalized quinoxalines and quinazolines
Co-phen/C-800 have been successfully used as an innovative, selective, reusable and efficient catalyst to generate a series of quinoxaline derivatives via coupling reaction between diamines and diols at 150 °C was described by Kundu et al. (Panja et al. 2020) (Scheme 9.34).
Co-phen/C-800 catalyzed synthesis of quinoxaline derivatives
In situ formed alcohols and nitroarenes using tricarbonyl (η4-cyclopentadienone) iron complex have been successfully used as simple and efficient reactant for the Pictet-Spengler-type annulation/oxidation reaction to access the quinoxaline derivatives at 160 °C was developed by Hong et al. (Chun et al. 2020) (Scheme 9.35).
Pictet-Spengler-type annulation/oxidation reaction to access the quinoxaline derivatives
Zahouily et al. (Dânoun et al. 2020) depicted eco-friendly synthesis of functionalized quinoxalines via nanostructured Na2PdP2O7 catalyzed condensation reaction of aryl 1,2-dicarbonyl and diamines in EtOH at room temperature. The used bifunctional heterogeneous catalyst is reusable for the next five consecutive cycles (Scheme 9.36).
Synthesis of functionalized quinoxalines via nanostructured Na2PdP2O7 catalyzed condensation reaction
Chen et al. (Xie et al. 2016) developed an environmentally benign process to afford quinoxaline derivatives through one-pot domino reaction of 2-pyrrol-1-ylaniline[2-(1H-pyrrol-1-yl)phenyl]amine and a variety of β-diketones catalyzed by Brønsted acid (TsOH·H2O) in DMSO at 110 °C (Scheme 9.37).
Brønsted acid (TsOH·H2O) catalyzed synthesis of quinoxaline derivatives
Gi et al. (Cho and Oh 2006) demonstrated a ruthenium RuCl2(PPh3)3-catalyzed reaction of o-phenylene diamines and vicinal diols to generate a series of quinoxalines in the presence of KOH and diglyme at reflux (Scheme 9.38).
Ruthenium RuCl2(PPh3)3-induced reaction of o-phenylene diamines and vicinal diols to generate a series of quinoxalines
Lindsley et al. (Zhao et al. 2004) described a microwave-induced protocol to generate functionalized quinoxaline in 9:1 MeOH-HOAc at160 ℃ (Scheme 9.39).
Microwave-induced protocol to generate functionalized quinoxaline
Magnetically separable Fe3O4 nanoparticles were found a proficient catalyst to access substituted 2 quinoxalines in water was introduced by Zhang and co-workers (Lü et al., 2010). The used nano-catalyst is reusable (Scheme 9.40).
Magnetically separable Fe3O4 nanoparticles catalyzed synthesis of substituted 2 quinoxalines in water
9.5 Conclusion
This chapter emphasizes on effective and miscellaneous biological activities and synthetic methods of the fused N-heterocyclic compounds for example cinnoline, quinoxalines and quinazolines derivatives described in literature. It offers an viewpoint on modern advances of cinnoline, quinoxalines and quinazolines consuming numerous biological activities such as anticonvulsant, antifungal, antibacterial, antiulcer, antiinflammatory, anticancer, antimalarial, antitumor, antitubercular, antihypertensive, antihistamine, antidiabetic and antihypertensive. This chapter could be useful for other scientist to advanced important drugs having these moieties for the treatment of numerous deadly syndromes in future. Cinnoline, quinoxalines and quinazolines derivatives are considered as significant precursor to synthesize numerous biologically important scaffolds. In this chapter, we hope to deliver an overview of the significant common approaches for manufacturing these moieties and current progresses toward their biological activity and exposed the entrance for upcoming research in this field.
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Saini, P. et al. (2022). An Overview of Cinnolines, Quinazolines and Quinoxalines: Synthesis and Pharmacological Significance. In: Ameta, K.L., Kant, R., Penoni, A., Maspero, A., Scapinello, L. (eds) N-Heterocycles. Springer, Singapore. https://doi.org/10.1007/978-981-19-0832-3_9
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