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

doi:10.1080/17415993.2014.933340

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

Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	596-605
Number of pages	10
Journal	Journal of Sulfur Chemistry
Volume	35
Issue number	6
DOIs	https://doi.org/10.1080/17415993.2014.933340
State	Published - 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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10.1080/17415993.2014.933340

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

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.",

keywords = "X-ray crystal structure, cyanoborohydride salt, pyrroles, ring closure, thiophenes",

author = "Tice, {Nathan C.} and Peak, {Sarah M.} and Cannon, {Benjamin T.} and Laha, {Ethan S.} and Estes, {Eli G.} and Snyder, {Chad A.} and Sean Parkin",

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: {\textcopyright} 2014 Taylor & Francis.",

year = "2014",

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doi = "10.1080/17415993.2014.933340",

language = "English",

volume = "35",

pages = "596--605",

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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 - 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.

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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