Microwave-assisted three-component coupling-addition-SNAr (CASNAR) sequences to annelated 4H-thiopyran-4-ones

Organic and Biomolecular Chemistry

Volumn 8, Issue 1, 2010, Pages 90-95

  Willy, Benjamin ^a   Frank, Walter ^a   Müller, Thomas J J ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION BAND; DFT CALCULATION; ELECTRONIC GROUND STATE; GOOD YIELD; MICROWAVE-ASSISTED; ONE POT; SODIUM SULFIDES; STRUCTURAL UNIT; THREE COMPONENT REACTIONS; THREE-COMPONENT COUPLING;

ACETYLENE; CHLORINE COMPOUNDS; SODIUM; SODIUM COMPOUNDS; SULFUR COMPOUNDS;

MICROWAVES;

PYRAN DERIVATIVE; THIOL DERIVATIVE; THIOPYRAN;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; ELECTRON; METHODOLOGY; MICROWAVE RADIATION; SPECTROPHOTOMETRY; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; ELECTRONS; MICROWAVES; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRANS; SPECTROPHOTOMETRY; SULFHYDRYL COMPOUNDS;

EID: 76849117301     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b917627f     Document Type: Article

References (38)

1. H. Nakazumi, T. Ueyama and T. Kitao, J. Het. Chem., 1985, 22, 1593.
2. H. Nakazumi, T. Ueyama and T. Kitao, J. Het. Chem., 1984, 21, 193.
3. J. Couquelet, P. Tronche, P. Niviere and G. Andraud, Trav. Soc. Pharm. Montpellier, 1963, 23, 214.
4. M. H. Holshouser, L. J. Loeffler and I. H. Hall, J. Med. Chem., 1981, 24, 853.
5. R. K. Razdan, R. J. Bruni, A. C. Mehta, K. K. Weinhardt and Z. B. Papanastassiou, J. Med. Chem., 1978, 21, 643.
6. D. Dhanak, R. M. Keenan, G. Burton, A. Kaura, M. G. Darcy, D. H. Shah, L. H. Ridgers, A. Breen, P. Lavery, D. G. Tew and A. West, Bioorg. Med. Chem. Lett., 1998, 8, 3677.
7. F. Bossert, Liebigs Ann. Chem., 1964, 40, 680;
8. S. W. Schneller, Adv. Heterocycl. Chem., 1975, 18, 59;
9. H. Nakazumi, S. Wanatabe, T. Kitaguchi and T. Kitao, Bull. Chem. Soc. Jpn., 1990, 63, 847.
10. W. E. Truce and D. L. Goldhamer, J. Am. Chem. Soc., 1959, 81, 5795;
11. K. Buggle, J. J. Delahunty, E. M. Philbin and N. D. Ryan, J. Chem. Soc. C, 1971, 3168.
12. A. J. Angel, A. E. Finefrock, K. L. French, D. R. Hurst, A. R. Williams, M. E. Rampey, S. L. Studer-Martinez and C. F. Beam, Can. J. Chem., 1999, 77, 94.
13. K. L. French, A. J. Angel, A. R. Williams, D. R. Hurst and C. F. Beam, J. Heterocycl. Chem., 1998, 35, 45.
14. P. Kumar, A. T. Rao and B. Pandey, J. Chem. Soc., Chem. Commun., 1992, 1580;
15. P. Kumar and M. S. Bodas, Tetrahedron, 2001, 57, 9755.
16. D. H. Wadsworth and M. R. Detty, J. Org. Chem., 1980, 45, 4611.
17. For reviews, see: B. Willy and T. J. J. Müller, ARKIVOC, 2008, Part (i), 195;
18. B. Willy and T. J. J. Müller, Curr. Org. Chem., 2009, 13, 1777, DOI: 10.2174/138527209789630479.
19. B. Willy and T. J. J. Müller, Synlett, 2009, 1255.
20. For lead reviews on Sonogashira couplings, see e.g.: S. Takahashi, Y. Kuroyama, K. Sonogashira and N. Hagihara, Synthesis, 1980, 627;
21. K. Sonogashira, in Metal catalyzed cross-coupling reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, p. 203;
22. H. Doucet and J.-C. Hierso, Angew. Chem., Int. Ed., 2007, 46, 834;
23. L. Yin and J. Liebscher, Chem. Rev., 2007, 107, 133.
24. Y. Toda, K. Sonogashira and N. Hagihara, Synthesis, 1977, 777.
25. A. S. Karpov and T. J. J. Müller, Org. Lett, 2003, 5, 3451;
26. D. M. D'Souza and T. J. J. Müller, Nat. Protoc, 2008, 3, 1660.
27. T. J. J. Müller, Chimica Oggi/Chemistry Today, 2007, 25, 70;
28. T. J. J. Müller, Targets in Heterocyclic Systems, 2006, 10, 54;
29. B. Willy and T. J. J. Müller, Eur. J. Org. Chem., 2008, 4157.
30. B. Willy, F. Rominger and T. J. J. Müller, Synthesis, 2008, 293;
31. B. Willy, W. Frank, F. Rominger and T. J. J. Müller, J. Organomet. Chem., 2009, 694, 942;
32. A. V. Rotaru, I. D. Druta, T. Oeser and T. J. J. Müller, Helv. Chim. Acta, 2005, 88, 1798.
33. M. S. Shvartsberg and I. D. Ivanchikova, ARKIVOC, 2003, (13), 87;
34. I. D. Ivanchikova and M. S. Shvartsberg, Russ. Chem. Bull., 2004, 53, 2303.
35. A. Couture, P. Grandclaudon and E. Huguerre, Synthesis, 1989, 456;
36. J. Becher, M. C. Christensen, M. C. Möller and J. Winckelmann, Sulfur Lett., 1982, 1, 43.
37. R. G. Pearson, Inorg. Chim. Acta, 1995, 240, 93.
38. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, GAUSSIAN 03 (Revision B.3), Gaussian, Inc., Wallingford, CT, 2004.