Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Regioselective Synthesis of Thieno[2,3-b]quinolin-4(9H)-ones: Occurrence of Thermal [1,3] Sigmatropic Rearrangement. K. C. Majumdar*, M. Ghosh, M. JanaDepartment of Chemistry, University of Kalyani, Kalyani -741235, W.Bengal., Indiae-Mail: kcm@klyuniv.ernet.in; Recommend Article Abstract Buy Article All articles of this category Abstract A number of hitherto unreported thieno[2,3-b]quinolin-4(9H)-ones 5a-f have been regioselectively synthesized from the corresponding 4-(prop-2-ynyloxy)quinolin-2(1H)-thiones 4a-f. The 4-(Prop-2-ynyloxy)quinolin-2(1H)-thiones 4a-f were prepared by the thionation of 4-(prop-2-ynyloxy)quinolin-2(1H)-ones 3a-f. The latter compounds were in turn prepared by the alkylation of 4-hydroxyquinolin-2(1H)-one (1). Key words Claisen rearrangement - [1,3] sigmatropic rearrangement - sulfur heterocycles - thieno[2,3-b]quinolin-4(9H)-one - [3,3]sigmatropic rearrangement Full Text References References 1 Jurd L. Benson M. J. Chem. Soc., Chem. Commun. 1983, 92: 2a Brown RFC. Hobbs JJ. Hughes GK. Ritchie E. Austr. J. Chem. 1954, 7: 348 2b Brown RFC. Hughes GK. Ritchie E. Chem. Ind. (London) 1955, 1385 2c Danieli L. Weitman NR. Glotter E. Tetrahedron 1968, 24: 3011 2d Dreyer DL. Lee A. Phytochemistry 1972, 11: 763 2e Taylor DR. Warner JM. Phytochemistry 1973, 12: 1359 2f Reisch J. Korosi J. Szendrei K. Novak I. Minker E. Phytochemistry 1975, 14: 1678 3a Grundon MF. Green RJ. Caston JC. J. Chem. Res. (M) 1985, 5: 1877 3b Kappe Th. Fritz PF. Ziegler E. Chem. Ber. 1973, 106: 1927 3c Rao VS. Darbarwar M. Synth. Commun. 1989, 19: 2713 3d Reish J. Bethe A. Arch. Pharm. (Weinheim, Ger.) 1987, 320: 737 3f Reisch J. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1967, 300: 533 4a Hoffman JW. Hsu TM. Tetrahedron Lett. 1972, 141 4b Groot A. Jansen JM. Tetrahedron Lett. 1975, 3407 4c Bowman RM. Grundon MF. James KJ. J. Chem. Soc., Perkin Trans. 1 1973, 1055 4d Ramesh M. Mohon PS. Shanmugam P. Tetrahedron 1984, 40: 4041 4e Reisch J. Bathe A. Rosenthal BHW. Salehi A. Reza A. J. Heterocycl. Chem. 1987, 24: 869 5a Majumdar KC. Choudhuri PK. Heterocycles 1991, 32: 73 5b Majumdar KC. Bhattacharyya T. J. Chem. Res. (S) 1997, 244 ; J .Chem. Res. (M); 1997, 1701 5c Majumdar KC. Bhattacharyya T. J. Chem. Res. (M) 1997, 1701 6 Majumdar KC. Choudhury PK. Synth. Commun. 1993, 23: 1087 7a Majumdar KC. Kundu AK. Chatterjee P. J. Chem. Res. (S) 1995, 386 7b Majumdar KC. Kundu AK. Chatterjee P. J. Chem. Res. (M) 1995, 2301 8 Majumdar KC. Kundu AK. Heterocycles 1997, 45: 1467 9 Majumdar KC. Kundu AK. Biswas P. Heterocycles 1999, 51: 471 10 Gilchrist TL. Storr RC. In Organic Reactions and Orbital Symmetry Cambridge Univ. Press; Cambridge: 1979. p.257 11 Mortensen JZ. Hedegward B. Lawesson SO. Tetrahedron 1971, 27: 3831 12 Majumdar KC. Saha S. De R N. Ghosh SK. J. Chem. Soc., Perkin Trans. 1 1993, 715 13 Majumdar KC. Jana NK. Bandyopadhyay A. Ghosh SK. Synth. Commun. 2001, 31: 2979 14 Majumdar KC. Jana GH. Heterocycles 1996, 4: 43 15 Majumdar KC. Jana GH. Synthesis 2001, 924
