Synthesis of 2,3-dihydro-1: H -pyrroles by intramolecular cyclization of N -(3-butynyl)-sulfonamides

Min Ching Chung; Yung Hsiang Chan; Wen Jung Chang; Duen Ren Hou

doi:10.1039/c7ob00528h

Synthesis of 2,3-dihydro-1: H -pyrroles by intramolecular cyclization of N -(3-butynyl)-sulfonamides

Min Ching Chung, Yung Hsiang Chan, Wen Jung Chang, Duen Ren Hou

Department of Chemistry

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9 Scopus citations

Abstract

Hydroamination of 3-butynamine derivatives to give non-aromatic 2,3-dihydropyrroles was achieved by using PdCl₂ or AuCl as the catalyst. With microwave-assisted heating, up to 92% isolated yield was obtained from this intramolecular 5-endo-dig cyclisation. The cyclopentane- and cyclohexane-fused 2,3-dihydropyrroles were transformed into the corresponding N-tosyl-pyrrolidine-2-carboxylic acids.

Original language	English
Pages (from-to)	3783-3790
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	17
DOIs	https://doi.org/10.1039/c7ob00528h
State	Published - 2017

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10.1039/c7ob00528h

CCDC 1522351: Experimental Crystal Structure Determination
Chung, M.-C. (Creator), Chan, Y.-H. (Creator), Chang, W.-J. (Creator) & Hou, D.-R. (Creator), The Cambridge Structural Database, 2017
DOI: 10.5517/ccdc.csd.cc1n3430, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1n3430&sid=DataCite
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title = "Synthesis of 2,3-dihydro-1: H -pyrroles by intramolecular cyclization of N -(3-butynyl)-sulfonamides",

abstract = "Hydroamination of 3-butynamine derivatives to give non-aromatic 2,3-dihydropyrroles was achieved by using PdCl2 or AuCl as the catalyst. With microwave-assisted heating, up to 92% isolated yield was obtained from this intramolecular 5-endo-dig cyclisation. The cyclopentane- and cyclohexane-fused 2,3-dihydropyrroles were transformed into the corresponding N-tosyl-pyrrolidine-2-carboxylic acids.",

author = "Chung, {Min Ching} and Chan, {Yung Hsiang} and Chang, {Wen Jung} and Hou, {Duen Ren}",

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doi = "10.1039/c7ob00528h",

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volume = "15",

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TY - JOUR

T1 - Synthesis of 2,3-dihydro-1

T2 - H -pyrroles by intramolecular cyclization of N -(3-butynyl)-sulfonamides

AU - Chung, Min Ching

AU - Chan, Yung Hsiang

AU - Chang, Wen Jung

AU - Hou, Duen Ren

N1 - Publisher Copyright: © The Royal Society of Chemistry 2017.

PY - 2017

Y1 - 2017

N2 - Hydroamination of 3-butynamine derivatives to give non-aromatic 2,3-dihydropyrroles was achieved by using PdCl2 or AuCl as the catalyst. With microwave-assisted heating, up to 92% isolated yield was obtained from this intramolecular 5-endo-dig cyclisation. The cyclopentane- and cyclohexane-fused 2,3-dihydropyrroles were transformed into the corresponding N-tosyl-pyrrolidine-2-carboxylic acids.

AB - Hydroamination of 3-butynamine derivatives to give non-aromatic 2,3-dihydropyrroles was achieved by using PdCl2 or AuCl as the catalyst. With microwave-assisted heating, up to 92% isolated yield was obtained from this intramolecular 5-endo-dig cyclisation. The cyclopentane- and cyclohexane-fused 2,3-dihydropyrroles were transformed into the corresponding N-tosyl-pyrrolidine-2-carboxylic acids.

UR - http://www.scopus.com/inward/record.url?scp=85021625289&partnerID=8YFLogxK

U2 - 10.1039/c7ob00528h

DO - 10.1039/c7ob00528h

M3 - 期刊論文

C2 - 28406511

AN - SCOPUS:85021625289

SN - 1477-0520

VL - 15

SP - 3783

EP - 3790

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 17

ER -

Synthesis of 2,3-dihydro-1: H -pyrroles by intramolecular cyclization of N -(3-butynyl)-sulfonamides

Abstract

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CCDC 1522351: Experimental Crystal Structure Determination

Cite this