Synthesis, Table of Contents Synthesis 2015; 47(08): 1109-1116DOI: 10.1055/s-0034-1380131 paper © Georg Thieme Verlag Stuttgart · New York Synthesis of Pyrido[2,3-c]coumarin Derivatives by an Intramolecular Povarov Reaction Md. Belal a Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781 039, India , Deb K. Das a Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781 039, India , Abu T. Khan* a Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781 039, India b Vice-Chancellor, Aliah University, IIA/27, New Town, Near Eco-Space, Kolkata-700 156, West Bengal, India Email: atk@iitg.ernet.in › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract Fused pyrido[2,3-c]coumarin derivatives were prepared by an intramolecular Povarov reaction of 2-(propagyloxy)benzaldehydes with 3-aminocoumarins in the presence of 10 mol% of triflic acid as a catalyst in refluxing acetonitrile. Among the advantages of this protocol are shorter reaction times, good yields, and the absence of the need for aqueous workup and chromatographic separation. Key words Key wordsheterocycles - pyridines - coumarins - fused-ring systems - Diels–Alder reactions - cyclizations - catalysis Full Text References References 1a Kouznetsov VV. Tetrahedron 2009; 65: 2721 1b Glushkov VA, Tolstikov AG. Russ. Chem. Rev. 2008; 77: 137 2a Kappe CO, Murphree SS, Padwa A. Tetrahedron 1997; 53: 14179 2b Carruthers W. Cycloaddition Reactions in Organic Synthesis. Pergamon; Oxford: 1990 2c Pindur U, Lutz G, Otto C. Chem. Rev. 1993; 93: 741 2d Waldmann H. Synthesis 1994; 535 3a Twin H, Batey RA. Org. Lett. 2004; 6: 4913 3b Helmchen G, Karge R, Weetman J In Modern Synthetic Methods . Vol. 4. Scheffold R. Springer; Berlin: 1986: 261 3c Shipman M. Contemp. Org. Synth. 1995; 2: 1 4a Ramesh S, Gaddam V, Nagarajan R. Synlett 2010; 757 4b Ramesh S, Nagarajan R. Tetrahedron Lett. 2011; 52: 4857 4c Gaddam V, Ramesh S, Nagarajan R. Tetrahedron 2010; 66: 4218 4d Tomashevskaya MM, Tomashenko OA, Tomashevskii AA, Sokolov VV, Potekhin AA. Russ. J. Org. Chem. 2007; 43: 77 4e Yadav JS, Reddy BV. S, Kondaji G, Sowjanya S, Nagaiah K. J. Mol. Catal. A: Chem. 2006; 258: 361 5a Tietze LF, Utecht J. Chem. Ber./Recl. 1992; 125: 2259 5b Beifuss U, Herde A, Ledderhose S. Chem. Commun. 1996; 1213 5c Laschat S. Liebigs Ann./Recl. 1997; 1 6a Kulkarni YD, Srivastava D, Bishnoi A, Dua PR. J. Indian Chem. Soc. 1996; 73: 173 6b Marcu MG, Schulte TW, Neckers L. J. Natl. Cancer Inst. 2000; 92: 242 6c Melagraki G, Afantitis A, Igglessi-Markopoulou O, Detsi A, Koufaki M, Kontogiorgis C, Hadjipavlou-Litina DJ. Eur. J. Med. Chem. 2009; 44: 3020 6d Rodighiero G, Antonello C. Boll. Chim. Farm. 1958; 97: 592 7a Evans BE, Rittle KE, Bock MG, Dipardo RM, Freidinger RM, Whitter GF, Lundell WL, Veber DF, Anderson PS, Cheng RS. L, Lotti VJ, Cerino DJ, Chen TB, Kling PJ, Kunkel KA, Springer JP, Hirshfield J. J. Med. Chem. 1988; 31: 2235 7b Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893 8a Khan MA, Gremal AL. J. Heterocycl. Chem. 1977; 14: 1009 8b Pavé G, Chalard P, Viaud-Massuard M.-C, Troin Y, Guillaumet G. Synlett 2003; 987 8c Majumdar KC, Chattopadhyay B, Taher A. Synthesis 2007; 3647 8d Kudale AA, Miller DO, Dawe LN, Bodwell GJ. Org. Biomol. Chem. 2011; 9: 7196 8e Kudale AA, Kendall J, Miller DO, Collins JL, Bodwell GJ. J. Org. Chem. 2008; 73: 8437 9a Howells RD, McCown JD. Chem. Rev. 1977; 77: 69 9b Manojveer S, Balamurugan R. Org. Lett. 2014; 16: 1712 9c Zhang X, Xu X, Yu L, Zhao Q. Tetrahedron Lett. 2014; 55: 2280 10a Khan AT, Khan MM. Tetrahedron Lett. 2011; 52: 3455 10b Zhu Z.-B, Shao L.-X, Shi M. Eur. J. Org. Chem. 2009; 2576 10c Xing X, Wu J, Dai W.-M. Tetrahedron 2006; 62: 11200 10d Aggarwal VK, Vennall GP, Davey PN, Newman C. Tetrahedron Lett. 1997; 38: 2569 10e Baudelle R, Melnyk P, Déprez B, Tartar A. Tetrahedron 1998; 54: 4125 11a Rohlmann R, Daniliuca C.-G, Mancheño OG. Chem. Commun. 2013; 49: 11665 11b Mieg F, Meyer C, Cossy J. Angew. Chem. Int. Ed. 2011; 50: 5932 11c Ramachandiran K, Karthikeyan K, Muralidharan D, Perumal PT. Tetrahedron Lett. 2010; 51: 3006 Supplementary Material Supplementary Material Supporting Information
