Summary.
The one-pot reaction of β-glycosyl amino acids with β-ketoesters in the presence of Amberlite IR-120 resin and 4 Å molecular sieve in refluxing toluene resulted in the respective dihydropyridones in fair to good yields.
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a) Chen C, Donald IA, Munoz B (1998) Tetrahedron Lett 39: 217; b) Coutts RT, Scott JR (1971) Can J Pharm Sci 6: 78; c) Stout DM, Meyers AI (1982) Chem Rev 82: 22; d) Yamaguchi R, Hata E, Matsuki T, Kawanisi M (1987) J Org Chem 52: 2094
a) Grenhill JV (1977) Chem Soc Rev 6: 277; b) Brown JD, Foley MA, Comins DL (1988) J Am Chem Soc 110: 7445; c) Rault S, Renault O, Guillon J, Dallemagne P, Pfeiffer B, Lestage P, Lebrun MC (2000) EP Patent 1, 050, 530; d) Goodman KB et al. (2007) J Med Chem 50: 6
AG Cook (1969) Enamines Marcel Dekker New York
a) Hamblett CL, Sloman DL, Kliman LT, Adams B, Ball RG, Stanton MG (2007) Tetrahedron Lett 48: 2079; b) Comins DL (1999) J Heterocycl Chem 36: 1491; c) Neipp CE, Martin SF (2003) J Org Chem 68: 8867; d) Comins DL, Brown JD (1986) Tetrahedron Lett 27: 4549; e) Brown JD, Foley MA, Comins DL (1988) J Am Chem Soc 110: 7445; f) Comins DL, LaMunyon DH (1989) Tetrahedron Lett 30: 5053; g) Comins DL, Zeller E (1991) Tetrahedron Lett 32: 5889; h) Imanishi T (1984) Yakugaku Zasshi 104: 549
EN Tzanetou KM Kasiotis P Magiatis SA Haroutounian (2007) Molecules 12 735 Occurrence Handle1:CAS:528:DC%2BD2sXltVygsLY%3D Occurrence Handle10.3390/12040735
a) Comins DL, Killpack MO (1992) J Am Chem Soc 114: 10972; b) Comins DL, Joseph SP, Goehring RR (1994) J Am Chem Soc 116: 4719; c) Renault O, Guillon J, Dallemagne P, Rault S (2000) Tetrahedron Lett 41: 681; d) Leflemme N, Dallemagne P, Rault S (2001) Tetrahedron Lett 42: 8997; e) Leflemme N, Dallemagne P, Rault S (2002) Synthesis 1740; f) Yuan Y, Li X, Ding K (2002) Org Lett 4: 3309; g) Waldmann H (1994) Synthesis 535; h) Badorrey R, Cativiela FC, Diaz-de-villegas MD, Galvez JA (2002) Tetrahedron 58: 341; i) Ming H, Struble JR, Bode JW (2006) J Am Chem Soc 128: 8418
a) Anderson TF, Knight JG, Tchabanenko K (2003) Tetrahedron Lett 44: 757; b) Kumar AS, Haritha B, Rao BV (2003) Tetrahedron Lett 44: 4261; c) Cardillo G, Fabbroni S, Gentilucci L, Perciaccante R, Piccinelli F, Tolomelli A (2004) Tetrahedron 60: 5031; d) Nedolya NA, Albanov AI, Klyba LV, Zhanchipova ER (2006) Russ J Org Chem 42: 455; e) Paravidino M, Bon RS, Scheffelaar R, Vugts DJ, Znabet A, Schmitz RF, Kanter FJJ, Lutz M, Spek AL, Groen MB, Orru RVA (2006) Org Lett 8: 5369; f) Davis FA, Xu H, Zhangb J (2007) J Org Chem 72: 2046; g) Liu J, Liang F, Qun Liu, Bing Li (2007) Synlett 1: 156
a) Khan AR, Tripathi RP, Tiwari VK, Mishra RC, Reddy VJM, Saxena JK (2002) J Carb Chem 21: 591; b) Tripathi RP, Tripathi R, Tiwari VK, Bala L, Sinha S, Srivastava A, Srivastava R, Srivastava BS (2002) Eur J Med Chem 37: 773; c) Tripathi RP, Rastogi SK, Kundu B, Saxena JK, Reddy VJM, Srivastava S, Chandra S, Bhaduri AP (2001) Comb Chem High Thro Scr 4: 237; d) Tewari N, Mishra RC, Tiwari VK, Tripathi RP (2002) SYNLETT 1779; e) Mishra RC, Tewari N, Arora K, Ahmad R, Tripathi RP, Tiwari VK, Walter RD, Srivatava AK (2003) Combi Chem High Thro Scr 6: 37; f) Mishra RC, Tripathi R, Katiyar D, Tewari N, Singh D, Tripathi RP (2003) Bio-Org Med Chem 11: 5363; g) Tiwari VK, Tripathi RP (2002) Ind J Chem 41B: 1681; h) Tiwari VK, Tewari N, Tripathi RP, Arora K, Gupta S, Srivastava AK, Khan AR, Murthy PK, Walter RD (2003) Bio Med Chem 11: 1789
a) Katiyar D, Mishra, RC, Tripathi RP (2004) J Carbohy Chem 23: 4; b) Mishra RC, Katiyar D, Tewari N, Tripathi RP (2004) Nucleosides, Nucleotides Nucleic Acids 23: 531; c) Tewari N, Tiwari VK, Mishra RC, Tripathi RP, Srivastava AK, Ahmad R, Srivastava R, Srivastava BS (2003) Bio Med Chem 11: 2911; d) Tewari N, Tiwari VK, Tripathi RP, Gaikwad A, Sinha S, Chaturvedi AK, Shukla PK, Srivastava R, Srivastava BS (2003) Bio Med Chem Lett 14: 329; e) Katiyar D, Tiwari VK, Tewari N, Verma SS, Sinha S, Giakwad A, Srivastava A, Chaturvedi V, Srivastava R, Srivastava BS, Tripathi RP (2005) Eu J Med Chem 40: 351; f) Tripathi RP, Tiwari VK, Tewari N, Katiyar D, Saxena N, Sinha S, Gaikwad A, Srivastava A, Chaturvedi V, Manju YK, Srivastava R, Srivastava BS (2005) Bio Med Chem 13: 5668; g) Dwivedi N, Mishra RC, Tripathi RP (2005) Lett Org Chem 2: 450
N Tewari D Katiyar VK Tiwari RP Tripathi (2003) Tetrahedron Lett 44 6639 Occurrence Handle10.1016/S0040-4039(03)01671-X Occurrence Handle1:CAS:528:DC%2BD3sXlvFOlsLg%3D
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Present address: Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi-221005, India.
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Tiwari, V., Tewari, N., Katiyar, D. et al. One-pot Amberlite IR-120 Catalysed Synthesis of Glycosyl Dihydropyridones. Monatsh. Chem. 138, 1297–1302 (2007). https://doi.org/10.1007/s00706-007-0729-8
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DOI: https://doi.org/10.1007/s00706-007-0729-8