The 1,3-dipolar cycloaddition of methyl acrylate to hindered 3-oxidopyraziniums

Madeleine Helliwell; Yun You; John A. Joule

doi:10.3987/COM-06-S(W)22

The 1,3-dipolar cycloaddition of methyl acrylate to hindered 3-oxidopyraziniums

Madeleine Helliwell, Yun You, John A. Joule

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

Abstract

- Methyl acrylate adds to 1,2,5,6-tetramethyl-3-oxidopyrazinium to give a standard 1,3-dipolar cycloadduct - a 3,8-diazabicyclo[3.2.1]octan-2-one - however from the more hindered 5,6-diethyl-1,2-dimethyl-3-oxidopyrazinium, a 4,7-dioxo-3,6-diazabicyclo[3.2.1]octane, the result of extensive rearrangement of the initial 1,3-dipolar cycloadduct, was obtained and its structure determined by X-Ray crystallographic analysis. © 2006 The Japan Institute of Heterocyclic Chemistry.

Original language	English
Pages (from-to)	87-91
Number of pages	4
Journal	Heterocycles
Volume	70
DOIs	https://doi.org/10.3987/COM-06-S(W)22
Publication status	Published - 31 Dec 2006

Keywords

3-oxidopyrazinium
1,3-dipolar cycloaddition
3,8-diazabicyclo[3.2.1]octan-2-one
4,7-dioxo-3,6-diazabicyclo[3.2.1]octane
pyrazin-2-one

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@article{ae3c61c717f54665aafac0a210a0ca73,

title = "The 1,3-dipolar cycloaddition of methyl acrylate to hindered 3-oxidopyraziniums",

abstract = "- Methyl acrylate adds to 1,2,5,6-tetramethyl-3-oxidopyrazinium to give a standard 1,3-dipolar cycloadduct - a 3,8-diazabicyclo[3.2.1]octan-2-one - however from the more hindered 5,6-diethyl-1,2-dimethyl-3-oxidopyrazinium, a 4,7-dioxo-3,6-diazabicyclo[3.2.1]octane, the result of extensive rearrangement of the initial 1,3-dipolar cycloadduct, was obtained and its structure determined by X-Ray crystallographic analysis. {\textcopyright} 2006 The Japan Institute of Heterocyclic Chemistry.",

keywords = "3-oxidopyrazinium, 1,3-dipolar cycloaddition, 3,8-diazabicyclo[3.2.1]octan-2-one, 4,7-dioxo-3,6-diazabicyclo[3.2.1]octane, pyrazin-2-one",

author = "Madeleine Helliwell and Yun You and Joule, {John A.}",

year = "2006",

month = dec,

day = "31",

doi = "10.3987/COM-06-S(W)22",

language = "English",

volume = "70",

pages = "87--91",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

}

TY - JOUR

T1 - The 1,3-dipolar cycloaddition of methyl acrylate to hindered 3-oxidopyraziniums

AU - Helliwell, Madeleine

AU - You, Yun

AU - Joule, John A.

PY - 2006/12/31

Y1 - 2006/12/31

N2 - - Methyl acrylate adds to 1,2,5,6-tetramethyl-3-oxidopyrazinium to give a standard 1,3-dipolar cycloadduct - a 3,8-diazabicyclo[3.2.1]octan-2-one - however from the more hindered 5,6-diethyl-1,2-dimethyl-3-oxidopyrazinium, a 4,7-dioxo-3,6-diazabicyclo[3.2.1]octane, the result of extensive rearrangement of the initial 1,3-dipolar cycloadduct, was obtained and its structure determined by X-Ray crystallographic analysis. © 2006 The Japan Institute of Heterocyclic Chemistry.

AB - - Methyl acrylate adds to 1,2,5,6-tetramethyl-3-oxidopyrazinium to give a standard 1,3-dipolar cycloadduct - a 3,8-diazabicyclo[3.2.1]octan-2-one - however from the more hindered 5,6-diethyl-1,2-dimethyl-3-oxidopyrazinium, a 4,7-dioxo-3,6-diazabicyclo[3.2.1]octane, the result of extensive rearrangement of the initial 1,3-dipolar cycloadduct, was obtained and its structure determined by X-Ray crystallographic analysis. © 2006 The Japan Institute of Heterocyclic Chemistry.

KW - 3-oxidopyrazinium

KW - 1,3-dipolar cycloaddition

KW - 3,8-diazabicyclo[3.2.1]octan-2-one

KW - 4,7-dioxo-3,6-diazabicyclo[3.2.1]octane

KW - pyrazin-2-one

U2 - 10.3987/COM-06-S(W)22

DO - 10.3987/COM-06-S(W)22

M3 - Article

SN - 0385-5414

VL - 70

SP - 87

EP - 91

JO - Heterocycles

JF - Heterocycles

ER -

The 1,3-dipolar cycloaddition of methyl acrylate to hindered 3-oxidopyraziniums

Abstract

Keywords

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