TY - JOUR
T1 - Synthesis of Novel Heterocycles from 2-Amino-3-(cyanomethylsulfonyl)thiophene
AU - Stephens, Chad E.
AU - Sowell, J. Walter
PY - 1998
Y1 - 1998
N2 - The synthesis and selected reactions of 2-amino-3-(cyanomethylsulfonyl)thiophene is reported. In particular, cyclization reaction of the versatile aminothiophene yielded a number of novel thieno[3,2-b][1,4]-thiazine 1,1-dioxides, as well as the analogous thieno[2,3-e][1,3,4]thiadiazine 4,4-dioxide. Reaction of the thienothiazine system with hydrazine was subsequently explored, which resulted in either ring-opening of the thiazine and formation of an aminopyrazole or solely ring cleavage depending on the thiazine substituent. Additionally, the synthesis of bis(2-amino-3-thienyl)sulfone and the corresponding bis-acetamide is described.
AB - The synthesis and selected reactions of 2-amino-3-(cyanomethylsulfonyl)thiophene is reported. In particular, cyclization reaction of the versatile aminothiophene yielded a number of novel thieno[3,2-b][1,4]-thiazine 1,1-dioxides, as well as the analogous thieno[2,3-e][1,3,4]thiadiazine 4,4-dioxide. Reaction of the thienothiazine system with hydrazine was subsequently explored, which resulted in either ring-opening of the thiazine and formation of an aminopyrazole or solely ring cleavage depending on the thiazine substituent. Additionally, the synthesis of bis(2-amino-3-thienyl)sulfone and the corresponding bis-acetamide is described.
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U2 - 10.1002/jhet.5570350424
DO - 10.1002/jhet.5570350424
M3 - Article
AN - SCOPUS:0013646769
SN - 0022-152X
VL - 35
SP - 927
EP - 931
JO - Journal of Heterocyclic Chemistry
JF - Journal of Heterocyclic Chemistry
IS - 4
ER -