TY - JOUR
T1 - The synthesis, characterization, and structure of a series of 4 H-thieno[3,4-c]pyrroles and their corresponding pyrrolium cyanoborohydride salts
AU - Tice, Nathan C.
AU - Peak, Sarah M.
AU - Cannon, Benjamin T.
AU - Laha, Ethan S.
AU - Estes, Eli G.
AU - Snyder, Chad A.
AU - Parkin, Sean
N1 - Publisher Copyright:
© 2014 Taylor & Francis.
PY - 2014/11/2
Y1 - 2014/11/2
N2 - A general, convenient route toward N-substituted 5,6-dihydro-4H-thieno[3,4-c]pyrroles was accomplished by the reductive amination of 2,5-dimethylthiophene-3,4-dicarbaldehyde with various primary amines in a solution of sodium cyanoborohydride and methanol/acetic acid (80-88% yield). For the N-alkyl cases, the product isolated was the cyanoborohydride salt of the desired product, 1,3-dimethyl-5-alkyl-5,6-dihydro-4H-thieno[3,4-c]-5-pyrrolium cyanoborohydride. For the aryl case employing aniline, the desired free pyrrole, 1,3-dimethyl-5-phenyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole, was isolated. X-ray crystallographic analysis of both the N-propyl and N-phenyl trials confirmed the salt and free amine nature of the products.
AB - A general, convenient route toward N-substituted 5,6-dihydro-4H-thieno[3,4-c]pyrroles was accomplished by the reductive amination of 2,5-dimethylthiophene-3,4-dicarbaldehyde with various primary amines in a solution of sodium cyanoborohydride and methanol/acetic acid (80-88% yield). For the N-alkyl cases, the product isolated was the cyanoborohydride salt of the desired product, 1,3-dimethyl-5-alkyl-5,6-dihydro-4H-thieno[3,4-c]-5-pyrrolium cyanoborohydride. For the aryl case employing aniline, the desired free pyrrole, 1,3-dimethyl-5-phenyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole, was isolated. X-ray crystallographic analysis of both the N-propyl and N-phenyl trials confirmed the salt and free amine nature of the products.
KW - X-ray crystal structure
KW - cyanoborohydride salt
KW - pyrroles
KW - ring closure
KW - thiophenes
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U2 - 10.1080/17415993.2014.933340
DO - 10.1080/17415993.2014.933340
M3 - Article
AN - SCOPUS:84943521281
SN - 1741-5993
VL - 35
SP - 596
EP - 605
JO - Journal of Sulfur Chemistry
JF - Journal of Sulfur Chemistry
IS - 6
ER -