Synthesis of morpholine or piperazine derivatives through gold-catalyzed cyclization reactions of alkynylamines or alkynylalcohols

Liang-Feng Yao; Yuan Wang; Kuo-Wei Huang

doi:10.1039/c5qo00060b

Synthesis of morpholine or piperazine derivatives through gold-catalyzed cyclization reactions of alkynylamines or alkynylalcohols

Liang-Feng Yao, Yuan Wang, Kuo-Wei Huang

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23 Scopus citations

Abstract

A convenient and efficient synthetic method for the construction of morpholine and piperazine derivatives in moderate to good yields was established. The reaction proceeds smoothly with 1.0 mol% gold catalyst loading. A plausible mechanism involving the cascade cyclization and isomerizations to produce the six-membered ring was proposed and supported by deuterium labeling experiments.

Original language	English (US)
Pages (from-to)	721-725
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	2
Issue number	6
DOIs	https://doi.org/10.1039/c5qo00060b
State	Published - Apr 20 2015

ASJC Scopus subject areas

Organic Chemistry

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10.1039/c5qo00060b

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title = "Synthesis of morpholine or piperazine derivatives through gold-catalyzed cyclization reactions of alkynylamines or alkynylalcohols",

abstract = "A convenient and efficient synthetic method for the construction of morpholine and piperazine derivatives in moderate to good yields was established. The reaction proceeds smoothly with 1.0 mol% gold catalyst loading. A plausible mechanism involving the cascade cyclization and isomerizations to produce the six-membered ring was proposed and supported by deuterium labeling experiments.",

author = "Liang-Feng Yao and Yuan Wang and Kuo-Wei Huang",

note = "KAUST Repository Item: Exported on 2021-12-14 Acknowledgements: We would like to acknowledge the financial support from the King Abdullah University of Science and Technology and the assistance given by the Core Laboratories.",

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doi = "10.1039/c5qo00060b",

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AU - Yao, Liang-Feng

AU - Wang, Yuan

AU - Huang, Kuo-Wei

N1 - KAUST Repository Item: Exported on 2021-12-14 Acknowledgements: We would like to acknowledge the financial support from the King Abdullah University of Science and Technology and the assistance given by the Core Laboratories.

PY - 2015/4/20

Y1 - 2015/4/20

N2 - A convenient and efficient synthetic method for the construction of morpholine and piperazine derivatives in moderate to good yields was established. The reaction proceeds smoothly with 1.0 mol% gold catalyst loading. A plausible mechanism involving the cascade cyclization and isomerizations to produce the six-membered ring was proposed and supported by deuterium labeling experiments.

AB - A convenient and efficient synthetic method for the construction of morpholine and piperazine derivatives in moderate to good yields was established. The reaction proceeds smoothly with 1.0 mol% gold catalyst loading. A plausible mechanism involving the cascade cyclization and isomerizations to produce the six-membered ring was proposed and supported by deuterium labeling experiments.

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ER -

Synthesis of morpholine or piperazine derivatives through gold-catalyzed cyclization reactions of alkynylamines or alkynylalcohols

Abstract

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