CuI-catalyzed cycloisomerization of propargyl amides

Ali Alhalib, Wesley J Moran

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The synthesis of substituted dihydrooxazoles by the CuI-catalyzed cycloisomerization of terminal propargyl amides is reported. The reaction has been shown to have good substrate scope and experiments to delineate the mechanism have been performed. Substrates containing a benzylic methylene were oxidized to the ketone under the reaction conditions.

Original languageEnglish
Pages (from-to)795-800
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number5
DOIs
Publication statusPublished - 7 Feb 2014

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Ketones
Amides
amides
Substrates
methylene
ketones
synthesis
Experiments

Cite this

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title = "CuI-catalyzed cycloisomerization of propargyl amides",
abstract = "The synthesis of substituted dihydrooxazoles by the CuI-catalyzed cycloisomerization of terminal propargyl amides is reported. The reaction has been shown to have good substrate scope and experiments to delineate the mechanism have been performed. Substrates containing a benzylic methylene were oxidized to the ketone under the reaction conditions.",
keywords = "1-Propanol, Amides, Catalysis, Copper, Cyclization, Iodides, Isomerism, Journal Article, Research Support, Non-U.S. Gov't",
author = "Ali Alhalib and Moran, {Wesley J}",
year = "2014",
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language = "English",
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journal = "Organic and Biomolecular Chemistry",
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CuI-catalyzed cycloisomerization of propargyl amides. / Alhalib, Ali; Moran, Wesley J.

In: Organic and Biomolecular Chemistry, Vol. 12, No. 5, 07.02.2014, p. 795-800.

Research output: Contribution to journalArticle

TY - JOUR

T1 - CuI-catalyzed cycloisomerization of propargyl amides

AU - Alhalib, Ali

AU - Moran, Wesley J

PY - 2014/2/7

Y1 - 2014/2/7

N2 - The synthesis of substituted dihydrooxazoles by the CuI-catalyzed cycloisomerization of terminal propargyl amides is reported. The reaction has been shown to have good substrate scope and experiments to delineate the mechanism have been performed. Substrates containing a benzylic methylene were oxidized to the ketone under the reaction conditions.

AB - The synthesis of substituted dihydrooxazoles by the CuI-catalyzed cycloisomerization of terminal propargyl amides is reported. The reaction has been shown to have good substrate scope and experiments to delineate the mechanism have been performed. Substrates containing a benzylic methylene were oxidized to the ketone under the reaction conditions.

KW - 1-Propanol

KW - Amides

KW - Catalysis

KW - Copper

KW - Cyclization

KW - Iodides

KW - Isomerism

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

U2 - 10.1039/c3ob42030b

DO - 10.1039/c3ob42030b

M3 - Article

VL - 12

SP - 795

EP - 800

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 5

ER -