Synthesis of Novel Heterocycles from 2-Amino-3-(cyanomethylsulfonyl)thiophene

Journal of Heterocyclic Chemistry

Volumn 35, Issue 4, 1998, Pages 927-931

  Stephens, Chad E ^a   Sowell Sr , J Walter ^a  

^a UNIVERSITY OF SOUTH CAROLINA COLLEGE OF PHARMACY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013646769     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570350424     Document Type: Article

References (14)

1. R. J. Mattson, L. C. Wang and J. W. Sowell, Sr., J. Heterocyclic Chem., 17, 1793 (1980).
2. C. E. Stephens and J. W. Sowell, Sr, J. Heterocyclic Chem., 34, 857 (1997).
3. D. L. Wang, S. M. Bayomi and J. W. Sowell, Sr., Pak. J. Sci. M. Res., 31, 242 (1988).
4. C. E. Stephens and J. W. Sowell, Sr., J. Heterocyclic Chem., 33, 1615 (1996).
5. K. Gewald, Chem. Ber., 98, 3571 (1965); Chem. Abstr., 64, 3451b (1966).
6. K. Gewald, Chem. Ber., 98, 3571 (1965); Chem. Abstr., 64, 3451b (1966).
7. Available as the dimeric l,4-dithiane-2,5-diol from Aldrich.
8. K. Gewald, Chem. Ber., 99, 94 (1966); Chem. Abstr., 64, 8118c (1966).
9. K. Gewald, Chem. Ber., 99, 94 (1966); Chem. Abstr., 64, 8118c (1966).
10. 1,8-Diazabicylco[5.4.0]undec-7-ene is routinely used with success in our laboratory for the synthesis of 2-amino-3-(arylsulfonyl)-thiophenes (unpublished).
11. The use of piperidine and 2 equivalents of mercaptoacetaldehyde also gave the bis-thiophene; however, triethylamine was found to give a cleaner and thus more readily purified product.
12. V. M. Neplyuev and T. A. Sinenko, Zh. Org. Khim., 14, 1953 (1978).
13. J. E. Mccormick and R. S. McElhinney, J. Chem. Soc., Perkin Trans 1, 1335 (1972).
14. R. G. Jones, J. Am. Chem. Soc., 73, 5168 (1951).