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

Publisher Copyright:
© 2014 Taylor & Francis.

Keywords

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

ASJC Scopus subject areas

  • General Chemistry

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