Stereospecific synthesis of functionalized C5-unsaturated hydantoin derivatives via a three-component reaction

Synthesis

Volumn , Issue 7, 2008, Pages 1061-1064

  Alizadeh, Abdolali ^a   Sheikhi, Ehsan ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Arylsulfonyl isocyanate; Dialkyl acetylenedicarboxylate; Hydantoin; Isoquinoline; Multicomponent reaction; Primary amine

Indexed keywords

ARYLSULFONYL ISOCYANATES; DIALKYL ACETYLENEDICARBOXYLATES; HYDANTOIN; ISOQUINOLINE; MULTICOMPONENT REACTION; PRIMARY AMINES;

AMINES; CARBOXYLATION; FUNCTIONAL GROUPS; REACTION KINETICS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

UNSATURATED COMPOUNDS;

ACETIC ACID DERIVATIVE; AMINE; ARYL SULFONYL ISOCYANATE; DIALKYL ACETYLENEDICARBOXYLATE; DICARBOXYLIC ACID DERIVATIVE; ETHYL(1 BENZYL 2,5 DIOXO 3 TOSYLIMIDAZOLIDIN 4 YLIDENE)ACETATE; ETHYL[1 (2 CHLOROBENZYL) 2,5 DIOXO 3 (PHENYLSULFONYL)IMIDAZOLIDIN 4 YLIDENE]ACETATE; ETHYL[1 (2 CHLOROBENZYL) 2,5 DIOXO 3 TOSYLIMIDAZOLIDIN 4 YLIDENE]ACETATE; ETHYL[1 BENZYL 2,5 DIOXO 3 (PHENYLSULFONYL)IMIDAZOLIDIN 4 YLIDENE]ACETATE; HYDANTOIN DERIVATIVE; ISOCYANIC ACID DERIVATIVE; ISOQUINOLINE; METHYL(1 BENZYL 2,5 DIOXO 3 TOSYLIMIDAZOLIDIN 4 YLIDENE)ACETATE; METHYL[1 (2 CHLOROBENZYL) 2,5 DIOXO 3 (PHENYLSULFONYL)IMIDAZOLIDIN 4 YLIDENE]ACETATE; METHYL[1 (2 CHLOROBENZYL) 2,5 DIOXO 3 TOSYLIMIDAZOLIDIN 4 YLIDENE]ACETATE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY;

EID: 42049092728     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1066993     Document Type: Article

References (29)

1. (a) Ware, E. Chem. Rev. 1950, 403.
2. (b) Spinks, A.; Waring, W. S. Prog. Med. Chem. 1963, 3, 313.
3. (c) Brouillete, W. J.; Jestkov, V. P.; Brown, M. L.; Akhtar, M. S.; Delorey, T. M.; Brown, G. B. J. Med. Chem. 1994, 37, 3289.
4. (d) Nefazi Giulianotti, M.; Truong, L.; Rattan, S.; Ostresh, J. M.; Houghten, R. A. J. Comput. Chem. 2002, 4, 175.
5. (a) Mizuno, T.; Kino, T.; Ito, T.; Miato, T. Synth. Commun. 2000, 30, 1675.
6. (b) Mappes, C. J.; Pommer, E. H.; Rentzea, C.; Zeeh, B. US 4,198,423, 1980; Chem. Abstr. 1980, 93, 71784.
7. Lavrador, K.; Guillerm, D.; Guillerm, G. Bioorg. Med. Chem. Lett. 1998, 8, 1629.
8. Tellier, F.; Acher, F.; Brabet, I.; Pin, J. P.; Azerad, R. Bioorg. Med. Chem. 1998, 6, 195.
9. (a) Avendano, C.; Menendez, J. C. Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 13; Wiley-Interscience: New York, 1995, 512.
10. (b) Guella, G.; Mancini, I; Zibrowius, H.; Pietra, F. Helv. Chim. Acta 1988, 71, 773.
11. (c) Lopez, C. A.; Trigo, G. G. Adv. Heterocycl. Chem. 1985, 38, 177.
12. (d) Bateman, J. H. Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 46; Wiley-Interscience: New York, 1950, 403.
13. Meanwell, N. A.; Roth, H. R.; Smith, E. C. R.; Wedding, D. L.; Wright, J. J. K. J. Org. Chem. 1991, 56, 6897.
14. Wheeler, H. L.; Hoffman, C.; Johnson, T. B. J. Biol. Chem. 1911, 45, 147.
15. Alizadeh, A.; Sheikhi, E. Tetrahedron Lett. 2007, 48, 4887.
16. Ulrich, H. Chem. Rev. 1962, 2, 186.
17. Adib, M.; Yavari, H.; Mollahosseini, M. Tetrahedron Lett. 2004, 45, 1803.
18. Ozaki, Sh. Chem. Rev. 1972, 72, 457.
19. (a) Huisgen, R. Proc. Chem. Soc., London 1961, 357.
20. (b) Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 633.
21. (c) Garner, P.; Ho, W. B.; Grandhee, S. K.; Youngs, W. J.; Kennedy, V. O. J. Org. Chem. 1991, 56, 5893.
22. (d) Garner, P.; Ho, W. B.; Shin, C. J. Am. Chem. Soc. 1993, 115, 10742.
23. (e) Monn, J. A.; Valli, M. J. Org. Chem. 1994, 59, 2773.
24. (f) Fiswick, C. W. G.; Foster, R. J.; Carr, R. E. Tetrahedron Lett. 1996, 37, 3915.
25. (a) Huisgen, R. Top. Heterocycl. Chem. 1969, 223.
26. (b) Huisgen, R. Z. Chem. 1968, 8, 290.
27. Huisgen, R.; Morikawa, M.; Herbig, K.; Brunn, E. Chem. Ber. 1967, 100, 1094.
28. Nair, V.; Sreekanth, A. R.; Abhilash, N.; Bhadbhade, M. M.; Gonnade, R. C. Org. Lett. 2002, 4, 3575.
29. Nair, V.; Sreekanth, A. R.; Biju, A. T.; Nigam, P. R. Tetrahedron Lett. 2003, 44, 729.