1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; First and second generation cycloaddition products

Frances Heaney; Elaine Lawless; Mary Mahon; Patrick McArdle; Desmond Cunningham

doi:10.1039/b602423h

1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; First and second generation cycloaddition products

Frances Heaney, Elaine Lawless, Mary Mahon, Patrick McArdle, Desmond Cunningham

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

11 Citations (Scopus)

Abstract

The reaction between the heteroaromatic N-oxides 1a, 1b and 1c with dimethyl acetylenedicarboxylate or methyl propiolate furnishes 1,3-benzodiazepines, the products of ring transformations of primarily formed cycloadducts. The structures of 8a and 10a have been confirmed by X-ray crystallographic analysis. The aldonitrone 1c also reacts with N-methylmaleimide and with phenyl vinyl sulfone to furnish the first examples of primary cycloaddition products from quinazoline 3-oxides.

Original language	English
Pages (from-to)	2408-2416
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	4
Issue number	12
DOIs	https://doi.org/10.1039/b602423h
Publication status	Published - 2006
Externally published	Yes

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abstract = "The reaction between the heteroaromatic N-oxides 1a, 1b and 1c with dimethyl acetylenedicarboxylate or methyl propiolate furnishes 1,3-benzodiazepines, the products of ring transformations of primarily formed cycloadducts. The structures of 8a and 10a have been confirmed by X-ray crystallographic analysis. The aldonitrone 1c also reacts with N-methylmaleimide and with phenyl vinyl sulfone to furnish the first examples of primary cycloaddition products from quinazoline 3-oxides.",

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T1 - 1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; First and second generation cycloaddition products

AU - Heaney, Frances

AU - Lawless, Elaine

AU - Mahon, Mary

AU - McArdle, Patrick

AU - Cunningham, Desmond

PY - 2006

Y1 - 2006

N2 - The reaction between the heteroaromatic N-oxides 1a, 1b and 1c with dimethyl acetylenedicarboxylate or methyl propiolate furnishes 1,3-benzodiazepines, the products of ring transformations of primarily formed cycloadducts. The structures of 8a and 10a have been confirmed by X-ray crystallographic analysis. The aldonitrone 1c also reacts with N-methylmaleimide and with phenyl vinyl sulfone to furnish the first examples of primary cycloaddition products from quinazoline 3-oxides.

AB - The reaction between the heteroaromatic N-oxides 1a, 1b and 1c with dimethyl acetylenedicarboxylate or methyl propiolate furnishes 1,3-benzodiazepines, the products of ring transformations of primarily formed cycloadducts. The structures of 8a and 10a have been confirmed by X-ray crystallographic analysis. The aldonitrone 1c also reacts with N-methylmaleimide and with phenyl vinyl sulfone to furnish the first examples of primary cycloaddition products from quinazoline 3-oxides.

UR - https://www.scopus.com/pages/publications/33745067201

U2 - 10.1039/b602423h

DO - 10.1039/b602423h

M3 - Article

SN - 1477-0520

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 12

ER -

1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; First and second generation cycloaddition products

Abstract

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