Abstract
Morpholinium 3-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-thiolate upon treatment with primary amines and a formaldehyde excess under mild conditions produces bis(pyrido[2,1-b][1,3,5]thiadiazin-7-yl)methane derivatives in good yields (67–87%).
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
For reviews on the 1,3,5-thiadiazine chemistry, see: a) Smalley RK (1996) 1,3,5-Oxadiazines and 1,3,5-Thiadiazines. In: Boulton AJ (ed) Comprehensive Heterocyclic Chemistry II, Vol. 6. Elsevier, Oxford, UK, p 783; b) Moody CJ (1984) Polyoxa, Polythia and Polyaza Six-Membered Ring Systems. In: Katritzky AR, Rees CW (eds) Comprehensive Heterocyclic Chemistry, Vol. 3. Pergamon, Oxford, UK, p 1039
a) Nakaya M, Fukushi Y, Shiraishi S, Nakamura M, Numata S, Kodaka K, Ooka M (1989) Pat EP 308961; (1989) Chem Abstr 111:174137a; b) Nihon Nohuyaku Co Ltd (1980) Pat Jpn 8053206; (1980) Chem Abstr 93:90206u
RA Coburn HO Cheun-huei ML Bronstein (1982) J Med Chem 25 481 Occurrence Handle10.1021/jm00346a028 Occurrence Handle1:CAS:528:DyaL38Xht1akt7Y%3D
For instance, see: a) Chen G, Zou J, Song X, Li Y (1996) Yaoxue Xuebao 31:425; (1997) Chem Abstr 126:29036x; b) Ilhan E, Capan G, Ergenc N, Uzun M, Kiraz M, Kaya B (1995) Farmaco 50(11):787; c) Ertan M, Bilgil AA, Palaska E, Yulug N (1992) Arzneim-Forsch (Drug Research) 42:160; d) Hussein MA, El-Shorbagi AN, Khallil AR (2001) Arch Pharm 334(10):305; e) Ertan M, Tayhan AB, Yulug N (1990) Arch Pharm 323(9):605; f) Saraç S, Ertan M, Balkan A, Yulug N (1991) Arch Pharm 324(7):449; g) El-Shorbagi AN (2000) Arch Pharm 333(9):281; h) Aboul-Fadl T, Hussein MA, El-Shorbagi AN, Khallil AR (2002) Arch Pharm 335(9):438
For instance, see: a) Chupp JP (1971) US Pat 3741964; (1973) Chem Abstr 79:78857k; b) Vicentini CB, Mares D, Tartari A, Manfrini M, Forlani G (2004) J Agr Food Chem 52:1898; c) Vicentini CB, Guccione S, Giurato L, Ciaccio R, Mares D, Forlani G (2005) J Agr Food Chem 53:3848
Ikeda K, Kanno H (1980) Pat Jpn 8013211; (1980) Chem Abstr 93:46729t
MG Dhonde GP Deshmukh (2005) Chem Heterocycl Compd 41 787 Occurrence Handle10.1007/s10593-005-0222-4 Occurrence Handle1:CAS:528:DC%2BD2MXht1WntbjN
R Pérez H Rodríguez E Pérez M Suárez O Reyes LJ González A López de Cerain O Ezpeleta C Pérez C Ochoa (2000) Arzneim-Forsch (Drug Research) 50 854
D Katiyar VK Tiwari RP Tripathi A Srivastava V Chaturvedi R Srivastava BS Srivastava (2003) Bioorg Med Chem 11 4369 Occurrence Handle10.1016/S0968-0896(03)00480-2 Occurrence Handle1:CAS:528:DC%2BD3sXnt1yisro%3D
T Aboul-Fadl ANA El-Shorbagi (1996) Eur J Med Chem 31 IssueID2 165 Occurrence Handle10.1016/0223-5234(96)80450-8 Occurrence Handle1:CAS:528:DyaK28XhvVGitLs%3D
ANA El-Shorbagi (1994) Eur J Med Chem 29 IssueID1 11 Occurrence Handle10.1016/0223-5234(94)90120-1 Occurrence Handle1:CAS:528:DyaK2cXit1Kksrk%3D
For brief review on the chemistry and biological activity of buprofezin, see: Kanno H (1987) Pure Appl Chem 59:1027
M Uchida T Asai T Sugimoto (1985) Agr Biol Chem 49 1233 Occurrence Handle1:CAS:528:DyaL2MXktVaisrw%3D
Y Izawa M Uchida T Sugimoto T Asai (1985) Pesticide Biochem Physiol 24 IssueID3 343 Occurrence Handle10.1016/0048-3575(85)90145-2 Occurrence Handle1:CAS:528:DyaL28XotlOnsQ%3D%3D
TX Liu TY Chen (2000) J Econ Entomol 93 234 Occurrence Handle1:CAS:528:DC%2BD3cXlslegsbc%3D Occurrence Handle10.1603/0022-0493-93.2.234
M Uchida Y Izawa T Sugimoto (1987) Pesticide Biochem Physiol 27 IssueID1 71 Occurrence Handle10.1016/0048-3575(87)90097-6 Occurrence Handle1:CAS:528:DyaL2sXotVeluw%3D%3D
V Manohar SVK Narasimha Murthy M Sirsi G Ramananda Rao PL Narasimha Rao (1975) J Pharm Sci 64 164 Occurrence Handle10.1002/jps.2600640140 Occurrence Handle1:CAS:528:DyaE2MXptlKguw%3D%3D
M Sakashita K Toyoda M Kitahara N Tsuruzoe S Nakayama K Oguchi (1993) Japan J Pharmacol 62 87 Occurrence Handle10.1254/jjp.62.87 Occurrence Handle1:CAS:528:DyaK3sXkt1Sgsr0%3D
L Monzote AM Montalvo L Fonseca R Perez M Suarez H Rodriguez (2005) Arzneim-Forsch (Drug Res) 55 IssueID4 232 Occurrence Handle1:CAS:528:DC%2BD2MXksFartLo%3D
J Coro R Atherton S Little H Wharton V Yardley A Alvarez M Suarez R Perez H Rodriguez (2006) Bioorg Med Chem Lett 16 1312 Occurrence Handle10.1016/j.bmcl.2005.11.060 Occurrence Handle1:CAS:528:DC%2BD28Xosl2itA%3D%3D
M Schorr W Durckheimer P Klatt G Lammler G Nesemann E Schrinner (1969) Arzneim-Forsch 19 1807 Occurrence Handle1:CAS:528:DyaE3cXjtVSrtw%3D%3D
HF Smyth SuffixJr CP Carpenter CS Weil (1966) Toxicol Appl Pharmacol 9 521 Occurrence Handle10.1016/0041-008X(66)90013-5 Occurrence Handle1:CAS:528:DyaF2sXhvValtQ%3D%3D
RI Babaeva (1989) Med Parazitol (Moskow) 2 25
S Sert A Ercag OS Sentürk BT Sterenberg KA Udachin Ü Özdemir FU Sarikahya (2003) Polyhedron 22 IssueID13 1689 Occurrence Handle10.1016/S0277-5387(03)00309-7 Occurrence Handle1:CAS:528:DC%2BD3sXkvVartL4%3D
Wang Zh, You T, Shi H, Shi H (1996) Molecules 1:89, avail. URL: http://www.springerlink.com
ZA Hozein AAO Sarhan HAH El-Sherief AM Mahmoud (1997) Z Naturforsch B Chem Sci 52 1401
Zh Wang H Shi H Shi (2001) Synth Commun 31 2841 Occurrence Handle10.1081/SCC-100105335 Occurrence Handle1:CAS:528:DC%2BD3MXmvVyisLk%3D
H Shi Zh Wang H Shi (1999) Synth Commun 29 2027 Occurrence Handle10.1080/00397919908086088 Occurrence Handle1:CAS:528:DyaK1MXis12gtLs%3D
H Shi Zh Wang H Shi (1997) Chimia 51 529
H Shi H Shi Zh Wang (2001) J Heterocycl Chem 38 929 Occurrence Handle1:CAS:528:DC%2BD3MXmtlersbw%3D
H Shi H Shi Zh Wang (2000) Youji Huaxue 20 344 Occurrence Handle1:CAS:528:DC%2BD3cXjs1eksrw%3D
H Shi H Shi Zh Wang (2000) Chem Abstr 133 120280c
Zh Wang T You H Shi H Shi (1997) Gaodeng Xuexiao Huaxue Xuebao 18 550
Zh Wang T You H Shi H Shi (1997) Chem Abstr 127 95265t
S Yadav Lal Dhar A Vaish S Sharma (1994) J Agric Food Chem 42 811 Occurrence Handle10.1021/jf00039a043
AAO Sarhan SH Abdel-Hafez H El-Sherief T Aboel-Fadl (2006) Synth Commun 36 987 Occurrence Handle10.1080/00397910500501243 Occurrence Handle1:CAS:528:DC%2BD28XisVaqsb4%3D
KA Frolov VV Dotsenko SG Krivokolysko VP Litvinov (2005) Russ Chem Bull Int Ed 54 IssueID9 2226 Occurrence Handle10.1007/s11172-006-0102-9 Occurrence Handle1:CAS:528:DC%2BD28XivVKjs70%3D
Hozein ZA (2000) J Chem Res Synop:99
VV Dotsenko SG Krivokolysko AN Chernega VP Litvinov (2003) Doklady Chemistry 389 IssueID4–6 92 Occurrence Handle10.1023/A:1023492608275 Occurrence Handle1:CAS:528:DC%2BD3sXjtVehtLY%3D
Dotsenko VV (2004) Cyanothioacetamide and its derivatives in the synthesis of ring-fused sulfur-containing pyridines, PhD Thesis. Zelinsky Institute of Organic Chemistry, p 167 (in Russian)
VV Dotsenko KA Frolov SG Krivokolysko AN Chernega VP Litvinov (2006) Monatsh Chem 137 1089 Occurrence Handle10.1007/s00706-006-0512-2 Occurrence Handle1:CAS:528:DC%2BD28XnslOit7c%3D
For reviews on the 3-cyanopyridine-2(1H)-thione chemistry, see: a) Litvinov VP, Rodinovskaya LA, Sharanin YuA, Shestopalov AM, Senning A (1992) Sulfur Rep 13:1; b) Litvinov VP (1993) Phosph Sulfur Silicon 74:139; c) Litvinov VP, Krivokolysko SG, Dyachenko VD (1999) Chem Heterocycl Compd 35(5):509; d) Litvinov VP (2006) Russ Chem Rev 75(7):645
VP Litvinov YuA Sharanin VK Promonenkov LA Rodinovskaya AM Shestopalov VYu Mortikov (1984) Russ Chem Bull 33 1706 Occurrence Handle10.1007/BF00959212
VD Dyachenko YuA Sharanin AM Shestopalov LA Rodinovskaya AV Turov VP Litvinov VK Promonenkov (1990) Zh Obsch Khim (Russ J Gen Chem) 60 IssueID10 2384 Occurrence Handle1:CAS:528:DyaK3MXlsFyqu7g%3D
VD Dyachenko (2006) Russ J Org Chem 42 940 Occurrence Handle10.1134/S1070428006060236 Occurrence Handle1:CAS:528:DC%2BD28XmvFSgtr0%3D
NN Kherfi M Hamdi V Speziale (1990) J Heterocycl Chem 27 IssueID5 1401 Occurrence Handle1:CAS:528:DyaK3MXmt1Cn Occurrence Handle10.1002/jhet.5570270540
IV Ukrainets LV Sidorenko OV Gorokhova OV Shishkin AV Turov (2006) Chem Heterocycl Compds 42 IssueID9 1208 Occurrence Handle10.1007/s10593-006-0228-6 Occurrence Handle1:CAS:528:DC%2BD2sXptlOqsQ%3D%3D
MT Cocco C Congiu V Onnis (2003) Eur J Med Chem 38 IssueID1 37 Occurrence Handle10.1016/S0223-5234(02)00002-8 Occurrence Handle1:CAS:528:DC%2BD3sXht1yqtrw%3D
M Cervera M Moreno-Manas R Pleixats (1990) Tetrahedron 46 IssueID23 7885 Occurrence Handle10.1016/S0040-4020(01)90086-9 Occurrence Handle1:CAS:528:DyaK3MXht1Wqt70%3D
MT Cocco C Congiu V Onnis (2000) Eur J Med Chem 35 IssueID5 545 Occurrence Handle10.1016/S0223-5234(00)00149-5 Occurrence Handle1:CAS:528:DC%2BD3cXkt1ais7k%3D
JA Findlay J Krepinsky FY Shum WHJ Tam (1976) Can J Chem 54 IssueID2 270 Occurrence Handle10.1139/v76-040 Occurrence Handle1:CAS:528:DyaE28XhtlGnsb8%3D
Author information
Authors and Affiliations
Corresponding author
Additional information
Correspondence: Victor V. Dotsenko, State Enterprise “Luganskstandartmetrology”, 91021 Lugansk, Ukraine.
Rights and permissions
About this article
Cite this article
Dotsenko, V., Krivokolysko, S. & Litvinov, V. An efficient Mannich-type synthesis of bis(pyrido[2,1-b][1,3,5]thiadiazin-7-yl)-methanes. Monatsh Chem 139, 657–661 (2008). https://doi.org/10.1007/s00706-007-0809-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-007-0809-9