A rich array of reactions of cyanomonothiocarbonylmalonamides RNHCSCH(CN)CONHR′ and their thioenols RNHC(SH)=C(CN)CONHR′

Journal of Organic Chemistry

Volumn 73, Issue 4, 2008, Pages 1386-1396

  Basheer, Ahmad ^a   Rappoport, Zvi ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL COMPOUNDS; NUCLEOPHILIC SUBSTITUTIONS; THIOENOL MOLECULE;

AMIDES; CRYSTALLIZATION; REACTION KINETICS;

AROMATIC COMPOUNDS;

AMIDE; CARBONYL DERIVATIVE; CYANODITHIOCARBONYLMALONAMIDE; CYANOMONOTHIOCARBONYLMALONAMIDE DERIVATIVE; CYCLOOCTANE DERIVATIVE; HETEROCYCLIC COMPOUND; SULFIDE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTALLIZATION; POLYMERIZATION; SUBSTITUTION REACTION;

EID: 39349111801     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7022262     Document Type: Article

References (54)

1. Preliminary report: Basheer, A.; Rappoport, Z. Kyushu International Symposium on Physical Organic Chemistry (KISPOC XI), Fukuoka September 12-15, 2005, Abstract O01.
2. (a) Mukhopadhyaya, J. K.; Sklenak, S.; Rappoport, Z. J. Am. Chem. Soc. 2000, 122, 1325.
3. (b) Mukhopadhyaya, J. K.; Sklenak, S.; Rappoport, Z. J. Org. Chem. 2000, 65, 6856.
4. (c) Lei, Y. X.; Cerioni, G.; Rappoport, Z. J. Org. Chem. 2000, 65, 4028.
5. (d ) Lei, Y. X.; Cerioni, G.; Rappoport, Z. J. Org. Chem. 2001, 66, 8379.
6. (e) Lei, Y. X.; Casarini, D.; Cerioni, G.; Rappoport, Z. J. Phys. Org. Chem. 2003, 16, 525.
7. (f) Lei, Y. X.; Casarini, D.; Cerioni, G.; Rappoport, Z. J. Org. Chem. 2003, 68, 947.
8. (g) Basheer, A.; Rappoport, Z. J. Org. Chem. 2004, 69, 1151.
9. (h) Basheer, A.; Yamataka, H.; Ammal, S. C.; Rappoport, Z. J. Org. Chem. 2007, 72, 5297.
10. (i) Song, J.; Yamataka, H.; Rappoport, Z. J. Org. Chem. 2007, 72, 7605.
11. Lei, Y. X.; Rappoport, Z. J. Org. Chem. 2002, 67, 6971.
12. Basheer, A.; Rappoport, Z. J. Org. Chem. 2006, 71, 9743.
13. Basheer, A.; Rappoport, Z. J. Org. Chem. 2008, 73, 184.
14. For examples of thioenols which were observed or investigated in solution, see: Sklenak, S.; Apeloig, Y.; Rappoport, Z. J. Chem. Soc., Perkin Trans. 2 2000, 2269, and ref 7.
15. Basheer, A.; Rappoport, Z. Submitted for publication.
16. "Formal" is used since in solution the three species 3, 4, and 5 are simultaneously present for most systems and the solid-state structure is not necessarily that in solution. When it seems reasonable that one of the species participates in a reaction, its structure is given.
17. Formation of a plethora of products, mostly heterocycles, from thioamides including cyanothioacetamides was reviewed (Jagodzinski, T. S. Chem. Rev. 2003, 103, 197;
18. Litvinov, V. P. Russ. Chem. Rev. 1999, 68, 737). None of the precursors is written as the thioenol, and only 2- N-substituted thioamido-1,3-indanedione may have the thioenol structure.
19. (a) Zhang, W.; Ricketts, W.; An, H.; Hong, Z. U.S. Patent 2004/0039037, February 26, 2004.
20. (b) Varaprasad, C. V. N. S.; Barawkar, D.; El Abdellaoui, H.; Chakravarty, S.; Allan, M.; Chen, H.; Zhang, W.; Wu, J. Z.; Tam, R.; Hamatake, R.; Lang, S.; Hong, Z. Bioorg. Med. Chem. Lett. 2006, 16, 3975.
21. (a) Vovk, M.; Sukach, V. A.; Chernega, A. N.; Pyrozhenko, V. V.; Bol'but, A. V.; Pinchuk, A. M. Heteroat. Chem. 2005, 16, 426.
22. (b) For an earlier work, see: Yokoyama, M. Bull. Chem. Soc. Jpn. 1971, 44, 1610.
23. (a) Almof, J.; Kvick, A.; Olovsson, I. Acta Crystallogr. 1971, B27,- 1201.
24. (b) Wheeler, G. L.; Ammon, H. L. Acta Crystallogr. 1974, B30, 680.
25. (c) Beak, P.; Fry, F. S., Jr. J. Am. Chem. Soc. 1973, 95, 1700.
26. For discussion on the pyridine-2-one/2-hydroxypyridine tautomerism in solution and the gas phase, see: (a) Beak, P. Acc. Chem. Res. 1977, 10, 186.
27. (b) Katritzky, A. R.; Karelson, M.; Malhorta, N. Heterocycles 1991, 32, 127.
28. (c) Katritzky, A. R.; Karelson, M.; Harris, P. A. Heterocycles 1991, 32, 329.
29. (d) March's Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, 6th ed.; Smith, M. B., March, J., Eds. Wiley: Hoboken, NJ, 2007; p 103.
30. (e) Forlani, L.; Cristoni, G.; Boga, C.; Todesco, P. E.; Del Vecchio, E.; Selva, S.; Monari, M. ARKIVOC 2002, X1, 198.
31. (a) Portnoy, S. J. Org. Chem. 1965, 30, 3377.
32. (b) Narsaiah, B.; Sivaprasad, A.; Venkatarnam, R. V. Org. Prep. Proced. Int. 1993, 25, 116.
33. (c) Greene, J. L.; Montgomery, J. A. J. Med. Chem. 1963, 6, 294.
34. (d) Maitraie, D. V.; Venkat Reddy, G.; Rama Rao, V. V. V. N. S.; Ravi Kanth, S.; Shanthan Rao, P.; Narsaiah, B. J. Fluorine Chem. 2002, 118, 73.
35. (a) Bernasconi, C. F.; Ketner, R. J.; Chen, X.; Rappoport, Z. Can. J. Chem. 1999, 77, 584;
36. ARKIVOC 2000, 161.
37. (b) Bernasconi, C. F.; Ketner, R. J.; Ragains, M. C.; Chen, X. Rappoport, Z. J. Am. Chem. Soc. 2001, 123, 2155.
38. (a) Yokoyama, M.; Shiraishi, T.; Hatanaka, H.; Ogata, K. Chem. Commun. 1985, 1704.
39. (b) Cmelik, R.; Marek, J.; Pazdera, P. Heterocycl. Commun. 2002, 8, 55.
40. (a) Antorrrena, G.; Dabies, J. E.; Hartley, M.; Palacio, F.; Rawson, J. M.; Smith, J. N. B.; Steiner, A. Chem. Commun. 1999, 1393.
41. (b) Bond, A. D.; Haynes, D. A.; Pask, C. M.; Rawson, J. M. J. Chem. Soc., Dalton Trans. 2002, 2522.
42. (c) Clarke, C. S.; Pascu, S. I.; Rawson, J. M. CrystEngComm 2004, 6, 79.
43. (d) Alberola, A.; Less, R. J.; Pask, C. M.; Rawson, J. M.; Palacio, F.; Oliete, P.; Paulsen, C.; Yamaguchi, A.; Farley, R. D.; Murphy, D. M. Angew. Chem., Int. Ed. 2003, 42, 4782.
44. (e) Heams, N. G. R.; Preuss, K. E.; Richardson, J. F.; Bin-Salamon, S. J. Am. Chem. Soc. 2004, 126, 9942.
45. (a) Beer, L.; Britten, J. F.; Clements, O. P.; Haddon, R. C.; Itkis, M. E.; Maikovich, K. M.; Oakley, R. T.; Reed, R. W. Chem. Mater. 2004, 16, 1564.
46. (b) Oakley, R. T.; Reed, R. W.; Robertson, C. M.; Richardson, J. F. Inorg. Chem. 2005, 44, 1837.
47. (c) Barclay, T. M.; Beer, L.; Cordes, A. W.; Oakley, R. T.; Preuss, K. E.; Taylor, N. J.; Reed, R. W. Chem. Commun. 1999, 531.
48. Kaawano, M.; Sano, T.; Abe, J.; Ohashi, Y. J. Am. Chem. Soc. 1999, 121, 8106.
49. Capozzi, G.; Modena, G. In The Chemistry of the Thiol Group; Patai, S., Ed.; Wiley: Chichester, UK, 1974; Chapter 17, p 785.
50. Basheer, A.; Rappoport, Z. Org. Lett. 2006, 8, 5931.
51. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1.
52. Closs, F.; Breimaier, W.; Frank, W.; Gompper, R.; Hohenester, A. Synth. Met. 1989, 29, E537.
53. Frey, J.; Rappoport, Z. J. Am. Chem. Soc. 1996, 118, 5169.
54. Lang, R. W.; Wenk, P. F. Helv. Chim. Acta 1988, 71, 596.