Synthesis and cycloaddition reactions of 2,3,4,5-tetrahydropyrazine 1-oxide

Mohammed I.M. Wazeer; Herman P. Perzanowski; Sajid I. Qureshi; Mohammad B. Al-Murad; Sk Asrof Ali

doi:10.1016/S0040-4020(00)00574-3

Synthesis and cycloaddition reactions of 2,3,4,5-tetrahydropyrazine 1-oxide

Mohammed I.M. Wazeer, Herman P. Perzanowski, Sajid I. Qureshi, Mohammad B. Al-Murad, Sk Asrof Ali

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

The stereochemistry and reactivity of the cycloaddition reactions of a heterocyclic nitrone, 2,3,4,5,-tetrahydropyrazine 1-oxide, have been studied. The heterocyclic nitrone is found to be more reactive than its carbocyclic counterpart. The nitrone underwent regio- and stereo-selective cycloaddition reaction with several alkenes to afford bicyclic isoxazolidines efficiently. Barriers to nitrogen inversion in the cycloadducts have been determined. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	7229-7236
Number of pages	8
Journal	Tetrahedron
Volume	56
Issue number	37
DOIs	https://doi.org/10.1016/S0040-4020(00)00574-3
State	Published - 8 Sep 2000

Keywords

Cycloadditions
Nitrones
Regiochemistry
Stereochemistry

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(00)00574-3

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title = "Synthesis and cycloaddition reactions of 2,3,4,5-tetrahydropyrazine 1-oxide",

abstract = "The stereochemistry and reactivity of the cycloaddition reactions of a heterocyclic nitrone, 2,3,4,5,-tetrahydropyrazine 1-oxide, have been studied. The heterocyclic nitrone is found to be more reactive than its carbocyclic counterpart. The nitrone underwent regio- and stereo-selective cycloaddition reaction with several alkenes to afford bicyclic isoxazolidines efficiently. Barriers to nitrogen inversion in the cycloadducts have been determined. (C) 2000 Elsevier Science Ltd.",

keywords = "Cycloadditions, Nitrones, Regiochemistry, Stereochemistry",

author = "Wazeer, \{Mohammed I.M.\} and Perzanowski, \{Herman P.\} and Qureshi, \{Sajid I.\} and Al-Murad, \{Mohammad B.\} and \{Asrof Ali\}, Sk",

year = "2000",

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doi = "10.1016/S0040-4020(00)00574-3",

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TY - JOUR

T1 - Synthesis and cycloaddition reactions of 2,3,4,5-tetrahydropyrazine 1-oxide

AU - Wazeer, Mohammed I.M.

AU - Perzanowski, Herman P.

AU - Qureshi, Sajid I.

AU - Al-Murad, Mohammad B.

AU - Asrof Ali, Sk

PY - 2000/9/8

Y1 - 2000/9/8

N2 - The stereochemistry and reactivity of the cycloaddition reactions of a heterocyclic nitrone, 2,3,4,5,-tetrahydropyrazine 1-oxide, have been studied. The heterocyclic nitrone is found to be more reactive than its carbocyclic counterpart. The nitrone underwent regio- and stereo-selective cycloaddition reaction with several alkenes to afford bicyclic isoxazolidines efficiently. Barriers to nitrogen inversion in the cycloadducts have been determined. (C) 2000 Elsevier Science Ltd.

AB - The stereochemistry and reactivity of the cycloaddition reactions of a heterocyclic nitrone, 2,3,4,5,-tetrahydropyrazine 1-oxide, have been studied. The heterocyclic nitrone is found to be more reactive than its carbocyclic counterpart. The nitrone underwent regio- and stereo-selective cycloaddition reaction with several alkenes to afford bicyclic isoxazolidines efficiently. Barriers to nitrogen inversion in the cycloadducts have been determined. (C) 2000 Elsevier Science Ltd.

KW - Cycloadditions

KW - Nitrones

KW - Regiochemistry

KW - Stereochemistry

UR - https://www.scopus.com/pages/publications/0034622876

U2 - 10.1016/S0040-4020(00)00574-3

DO - 10.1016/S0040-4020(00)00574-3

M3 - Article

AN - SCOPUS:0034622876

SN - 0040-4020

VL - 56

SP - 7229

EP - 7236

JO - Tetrahedron

JF - Tetrahedron

IS - 37

ER -

Synthesis and cycloaddition reactions of 2,3,4,5-tetrahydropyrazine 1-oxide

Abstract

Keywords

ASJC Scopus subject areas

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