Reactions of α-hydroxyketene dithioacetals with Lawesson's reagent: An efficient method for the synthesis of α,β-unsaturated dithioesters

Synthesis

Volumn , Issue 8, 2005, Pages 1261-1264

  Nair, Satheesh K ^a   Jose, Ann Maria ^a   Asokan, C V ^a  

^a MAHATMA GANDHI UNIVERSITY   (India)

Author keywords

Dithiocarboxylates; Heterodienes; Ketene dithioacetals; Lawesson's reagent; Thionation

Indexed keywords

ADDITION REACTIONS; CARBON; ESTERS; KETONES; REDUCTION; SYNTHESIS (CHEMICAL); UNSATURATED COMPOUNDS;

Α-HYDROXYKETENE DITHIOACETALS; Α-OXOKETENE DITHIOACETALS; CARBON NUCLEOPHILES; LAWESSON'S REAGENTS;

ACETAL RESINS;

3 (4 BROMOPHENYL) 3 METHYLPROP 2 ENE DITHIOATE; 3 (4 BROMOPHENYL)PROP 2 ENE DITHIOATE; 3 (4 CHLOROPHENYL)PROP 2 ENE DITHIOATE; 3 (4 METHYLPHENYL) 3 METHYLPROP 2 ENE DITHIOATE; 3 (4 METHYLPHENYL)PROP 2 ENE DITHIOATE; 3 PHENYL 3 PHENYL 3 METHYLPROP 2 ENE DITHIOATE; 3 PHENYLPROP 2 ENEDITHIOATE; ALPHA HYDROXYKETENE DITHIOACETAL DERIVATIVE; LAWESSON REAGENT; METHYL 1 METHYL 3,4 DIHYDRONAPHTHALENE 2 CARBODITHIOATE; METHYL 3 METHYLBUT 2 ENE DITHIOATE; METHYL 3,4 DIHYDRONAPHTHALENE 2 CARBODITHIOATE; REAGENT; THIOESTER; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 20344375729     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-865301     Document Type: Article

References (29)

1. (a) Metzner, P. Top. Curr. Chem. 1999, 204, 127.
2. (b) Boger, D. L. Tetrahedron 1983, 39, 2869.
3. (c) Barluenga, J.; Tomas, M. Adv. Heterocycl. Chem. 1993, 57, 1.
4. (a) Vedejs, E.; Stults, J. S. J. Org. Chem. 1988, 53, 2226.
5. (b ) Pinto, I. L.; Buckle, D. R.; Rami, H. K.; Smith, D. G. Tetrahedron Lett. 1992, 33, 7597.
6. (c) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Bonini, B. F.; Giannetto, P.; Nicolò, F. Tetrahedron: Asymmetry 1999, 10, 3919.
7. Al-Badri, H.; Collignon, N.; Maddaluno, J.; Massen, S. Tetrahedron 2000, 56, 3909.
8. Westmijze, H.; Kleijn, H.; Miejer, J.; Vermeer, P. Synthesis 1979, 432.
9. Gosselin, P.; Massen, S.; Thuillier, A. Tetrahedron Lett. 1980, 27, 2421.
10. (a) Massen, S.; Thuillier, A. Tetrahedron Lett. 1982, 23, 4087.
11. (b) Rettberg, N.; Wagner, U.; Hartke, K. Arch. Pharm. (Weinheim, Ger.) 1993, 326, 977.
12. (c) Lawson, K. R.; Singleton, A.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1984, 859.
13. Hartke, K.; Kunze, O. Liebigs Ann. Chem. 1989, 321.
14. Hoffman, R.; Hartke, K. Chem. Ber. 1980, 113, 919.
15. (a) Dieter, R. K. Tetrahedron 1986, 42, 3029.
16. (b) Junjappa, H.; Ha, H.; Asokan, C. V. Tetrahedron 1990, 46, 5423.
17. (c) Kolb, M. Synthesis 1990, 171.
18. (a) Saquet, M.; Thuillier, A. Bull. Soc. Chim. Fr. 1966, 3969.
19. (b) Dieter, R. K.; Jenkitkasemwong, Y.; Dieter, L. W. J. Org. Chem. 1984, 49, 3183.
20. (c) Dieter, R. K.; Jenkitkasemwong, Y. Tetrahedron Lett. 1982, 23, 3747.
21. (d) Myrboh, B.; Ila, H.; Junjappa, H. J. Org. Chem. 1983, 48, 5327.
22. (a) Myrboh, B.; Asokan, C. V.; Ila, H.; Junjappa, H. Synthesis 1984, 50.
23. (b) Asokan, C. V.; Ila, H.; Junjappa, H. Synthesis 1985, 163.
24. (c) Singh, G.; Purkayastha, M. L.; Ila, H.; Junjappa, H. J. Chem. Soc., Perkin Trans, 1 1985, 1289.
25. (d) Dieter, R. K.; Dieter, J. W. J. Chem. Soc., Chem. Commun. 1983, 1378.
26. Nair, S. K.; Asokan, C. V. Synth. Commun. 2001, 31, 1453.
27. Nair, S. K.; Asokan, C. V. Synth. Commun. 1999, 29, 791.
28. Nair, S. K.; Samuel, R.; Asokan, C. V. Synthesis 2001, 573.
29. Samuel, R.; Nair, S. K.; Asokan, C. V. Synlett 2000, 1804.