The synthesis, characterization, and structure of a series of 4 H-thieno[3,4-c]pyrroles and their corresponding pyrrolium cyanoborohydride salts

Nathan C. Tice, Sarah M. Peak, Benjamin T. Cannon, Ethan S. Laha, Eli G. Estes, Chad A. Snyder, Sean Parkin

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)596-605
Number of pages10
JournalJournal of Sulfur Chemistry
Volume35
Issue number6
DOIs
StatePublished - Nov 2 2014

Bibliographical note

Funding Information:
We wish to thank our sources of support for this research, including the Department of Chemistry, the Junior Faculty Summer ResearchAward from the College ofArts and Sciences and the Chemistry Diversity Initiative at Eastern Kentucky University. We also wish to thank Dr Jay Baltisberger at Berea College in Berea, KY for his support on the NMR spectroscopy.

Publisher Copyright:
© 2014 Taylor & Francis.

Keywords

  • X-ray crystal structure
  • cyanoborohydride salt
  • pyrroles
  • ring closure
  • thiophenes

ASJC Scopus subject areas

  • Chemistry (all)

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