Catalyst-free regioselective synthesis of benzopyran-annulated thiopyrano[2,3-b]thiochromen-5-(4H)-one derivatives by domino-Knoevenagel-hetero-Diels-Alder reaction of terminal alkynes with 4-hydroxy dithiocoumarin in aqueous medium

Tetrahedron Letters

Volumn 51, Issue 17, 2010, Pages 2297-2300

  Majumdar, K C ^a   Taher, Abu ^a   Ponra, Sudipta ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

4 Hydroxy dithiocoumarin; Domino Knoevenagel hetero Diels Alder reaction; Reaction in aqueous medium; Unactivated alkynes

Indexed keywords

4 HYDROXY DITHIOCOUMARIN; ALKENE DERIVATIVE; BENZOPYRAN DERIVATIVE; COUMARIN; SALICYLALDEHYDE; THIOPYRANOL[2,3 BETA]THIOCHROMEN 5 (4H) ONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

ALNUS;

EID: 77949567018     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.118     Document Type: Article

References (49)

1. Ellis G.P., Lockhart I.M., Meeder-Nycz D., and Schweizer E.E. In: Ellis G.P. (Ed). Chromenes, Chromanones and Chromones (1997), John Wiley and Sons
2. Feuer G. In: Ellis G.P., and West G.B. (Eds). Progress in Medicinal Chemistry (1974), North-Holland Publishing Co., New York
3. Kostova I. Curr. Med. Chem. Anti-Cancer Agents 5 (2005) 29
4. Wenkert E., and Buckwalter B.L. J. Am. Chem. Soc. 94 (1972) 4367
5. Deana A.A. J. Med. Chem. 26 (1983) 580
6. Vink, P. Neth. Appl.. 6, 411, 477 (Cl, Co7d), April 9, 1965, Swiss Appl. Oct. 8, 1963 and July 29, 1964; 7pp: Chem. Abstr. 1965, 63, 13265.
7. El-Subbagh H.I., El-Emam A.A., El-Ashmawy M.B., and Shehata I.A. Arch. Pharm. Res. 13 (1990) 24 and references cited therein
8. Korkina, G. L.; Afanas'ev, I. B. In Sies, H., Ed.; Adv. Pharmacol. 1997, 38, 151.
9. Buslig B.S. In: Manthy J.A. (Ed). Flavonoids in Living Systems: Advances in Experimental Medicine and Biology Vol. 439 (1998), Plenum, New York
10. Negwer M. Organic Chemical Drugs and their Synonyms. 7th ed. (1994), Akademie, Stuttgart
11. Groundwater P.W., Solomon K.R.H., Drewe J.A., and Munawar M.A. In: Ellis G.P., and Luscombe D.K. (Eds). Progress in Medicinal Chemistry Vol. 33 (1996), Elsevier, Amsterdam 233
12. Majumdar K.C., Khan A.T., and Saha S. Synlett (1991) 595
13. Majumdar K.C., Bandyopadhyay A., and Ghosh S.K. Synth. Commun. 34 (2004) 2159
14. Majumdar K.C., and Bandyopadhyay A. Monatsh. für Chem. 135 (2004) 581
15. Majumdar K.C., Saha S., and Khan A.T. Indian J. Chem. 33B (1994) 216
16. Majumdar K.C., Khan A.T., and Saha S. Synth. Commun. 22 (1992) 901
17. Majumdar K.C., Bandyopadhyay A., and Biswas A. Tetrahedron 59 (2003) 5289
18. Majumdar K.C., and Muhuri S. Synthesis (2006) 2725
19. Majumdar K.C., Kundu U.K., and Ghosh S.K. Org. Lett. 4 (2002) 2629
20. Majumdar K.C., Taher A., and Ray K. Tetrahedron Lett. 50 (2009) 3889
21. Yadav J.S., Reddy B.V.S., Sadashiv K., and Padmavani B. Adv. Synth. Catal. 346 (2004) 607
22. Yamanaka M., Nishida A., and Nakagana M. Org. Lett. 2 (2000) 159
23. Deligny M., Carreaux F., T oupet L., and Carboni B. Adv. Synth. Catal. 345 (2003) 1215
24. Berkessel A., Erturk E., and Laporte C. Adv. Synth. Catal. 348 (2006) 223
25. Baudelle R., Melnyk P., Deprez B., and Tartar A. Tetrahedron 54 (1998) 4125
26. Tietze L.F. Chem. Rev. 96 (1996) 115
27. Tietze L.F., Brasche G., and Gericke K. Domino Reactions in Organic Synthesis (2006), Wiley-VCH
28. Tietze L.F., and Rackelmann N. Pure Appl. Chem. 76 (2004) 1967
29. Tietze L.F., Ott C., Gerke K., and Buback M. Angew. Chem., Int. Ed. Engl. 32 (1993) 1485
30. Ramesh E., and Raghunathan R. Tetrahedron Lett. 49 (2008) 1812
31. Lee Y.R., and Xia L. Tetrahedron Lett. 49 (2008) 3283
32. Jimenez-Alonso S., Chavez H., Estevez-Braun A., Ravelo A.G., Feresin G., and Tapia A. Tetrahedron 64 (2008) 8938
33. Jimenez-Alonso S., Estevez-Braun A., Ravelo A.G., Zarate R., and Lopez M. Tetrahedron 63 (2007) 3066
34. Manikandan S., and Raghunathan R. Tetrahedron 58 (2002) 8957
35. Yadav J.S., Reddy B.V.S., Narsimhaswamy D., Lakshmi P.N., Narsimulu K., Srinivasulu G., and Kunwar A.C. Tetrahedron Lett. 45 (2004) 3493
36. Lee Y.R., Kim Y.M., and Kim S.H. Tetrahedron 65 (2009) 101
37. Khoshkholgh M.J., Balalaie S., Bijanzadeh H.R., and Gross J.H. Synlett (2009) 55
38. Khoshkholgh M.J., Balalaie S., Bijanzadeh H.R., and Gross J.H. ARKIVOC ix (2009) 114
39. Khoshkholgh M.J., Balalaie S., Bijanzadeh H.R., Rominger F., and Gross J.H. Tetrahedron Lett. 49 (2008) 6965
40. Khoshkholgh M.J., Balalaie S., Gleiter R., and Rominger F. Tetrahedron Lett. 49 (2008) 10924
41. Khoshkholgh M.J., Lotfi M., Balalaie S., and Rominger F. Tetrahedron 65 (2009) 4228
42. Majumdar K.C., Taher A., and Ponra S. Tetrahedron Lett. 51 (2010) 147
43. Bashiardes G., Safir I., Barbot F., and Laduranty J. Tetrahedron Lett. 45 (2004) 1567
44. Grieco P.A. Organic Synthesis in Water (1998), Blacky Academic & Professonal Publishers, London p. 82
45. Lindstrom U.M. Chem. Rev. 102 (2002) 2751
46. Li C.-J. Chem. Rev. 105 (2005) 3095
47. Li C.-J., and Chan T.-H. Comprehensive Organic Reactions in Aqueous Media (2007), Wiley and Sons, New York
48. Dai J., Munakata M., Wu L.-P., Sowa T.-K., and Suenaga Y. Inorg. Chim. Acta 258 (1997) 65
49. +: 337.0352; found; 337.0391.