EXTENDED TANDEM REACTIONS OF 2H-1,2,3-TRIAZOLE N-OXIDES WITH DIALKYL ACETYLENEDICARBOXYLATES AND N-PHENYLMALEIMIDE - SUBSTITUTED MONOCYCLIC 2,5-DIHYDRO-1,2,3-TRIAZINES AND NEW TETRAHYDROFURO[2,3-D]-1,2,3-TRIAZOLES - AZOLIUM 1,3-DIPOLES .5.

Patrick Mcardle

EXTENDED TANDEM REACTIONS OF 2H-1,2,3-TRIAZOLE N-OXIDES WITH DIALKYL ACETYLENEDICARBOXYLATES AND N-PHENYLMALEIMIDE - SUBSTITUTED MONOCYCLIC 2,5-DIHYDRO-1,2,3-TRIAZINES AND NEW TETRAHYDROFURO[2,3-D]-1,2,3-TRIAZOLES - AZOLIUM 1,3-DIPOLES .5.

Patrick Mcardle

Cellular & Molecular Medicine

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

Abstract

The reaction of substituted 1,2,3-triazole 1-oxides with dialkyl acetylenedicarboxylate dipolarophiles gave a new route to monocyclic 1,2,3-triazine derivatives via a multi-step sequence of cycloaddition, sigmatropic rearrangements, and ring expansion. With N-phenylmaleimide as dipolarophile, derivatives of a new tetrahydrofuro[2,3-d]-1,2,3-triazole system were formed. Mechanisms are discussed. An X-ray crystal structure of 2-(p-bromophenyl)-5-methoxalyl-5-methoxycarbonyl-4,6-dimethyl-2,5-dihydro-1,2,3-triazine is reported.

Original language	English (Ireland)
Number of pages	6
Journal	Journal Of The Chemical Society-Perkin Transactions 1
Publication status	Published - 1 Dec 1990

Authors (Note for portal: view the doc link for the full list of authors)

Authors
BUTLER, RN,CUNNINGHAM, D,MARREN, EG,MCARDLE, P

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@article{162bcf75bcf440b5bbe3f12d69de75b8,

title = "EXTENDED TANDEM REACTIONS OF 2H-1,2,3-TRIAZOLE N-OXIDES WITH DIALKYL ACETYLENEDICARBOXYLATES AND N-PHENYLMALEIMIDE - SUBSTITUTED MONOCYCLIC 2,5-DIHYDRO-1,2,3-TRIAZINES AND NEW TETRAHYDROFURO[2,3-D]-1,2,3-TRIAZOLES - AZOLIUM 1,3-DIPOLES .5.",

abstract = "The reaction of substituted 1,2,3-triazole 1-oxides with dialkyl acetylenedicarboxylate dipolarophiles gave a new route to monocyclic 1,2,3-triazine derivatives via a multi-step sequence of cycloaddition, sigmatropic rearrangements, and ring expansion. With N-phenylmaleimide as dipolarophile, derivatives of a new tetrahydrofuro[2,3-d]-1,2,3-triazole system were formed. Mechanisms are discussed. An X-ray crystal structure of 2-(p-bromophenyl)-5-methoxalyl-5-methoxycarbonyl-4,6-dimethyl-2,5-dihydro-1,2,3-triazine is reported.",

author = "Patrick Mcardle",

year = "1990",

month = dec,

day = "1",

language = "English (Ireland)",

journal = "Journal Of The Chemical Society-Perkin Transactions 1",

}

EXTENDED TANDEM REACTIONS OF 2H-1,2,3-TRIAZOLE N-OXIDES WITH DIALKYL ACETYLENEDICARBOXYLATES AND N-PHENYLMALEIMIDE - SUBSTITUTED MONOCYCLIC 2,5-DIHYDRO-1,2,3-TRIAZINES AND NEW TETRAHYDROFURO[2,3-D]-1,2,3-TRIAZOLES - AZOLIUM 1,3-DIPOLES .5. / Mcardle, Patrick.
In: Journal Of The Chemical Society-Perkin Transactions 1, 01.12.1990.

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

TY - JOUR

T1 - EXTENDED TANDEM REACTIONS OF 2H-1,2,3-TRIAZOLE N-OXIDES WITH DIALKYL ACETYLENEDICARBOXYLATES AND N-PHENYLMALEIMIDE - SUBSTITUTED MONOCYCLIC 2,5-DIHYDRO-1,2,3-TRIAZINES AND NEW TETRAHYDROFURO[2,3-D]-1,2,3-TRIAZOLES - AZOLIUM 1,3-DIPOLES .5.

AU - Mcardle, Patrick

PY - 1990/12/1

Y1 - 1990/12/1

N2 - The reaction of substituted 1,2,3-triazole 1-oxides with dialkyl acetylenedicarboxylate dipolarophiles gave a new route to monocyclic 1,2,3-triazine derivatives via a multi-step sequence of cycloaddition, sigmatropic rearrangements, and ring expansion. With N-phenylmaleimide as dipolarophile, derivatives of a new tetrahydrofuro[2,3-d]-1,2,3-triazole system were formed. Mechanisms are discussed. An X-ray crystal structure of 2-(p-bromophenyl)-5-methoxalyl-5-methoxycarbonyl-4,6-dimethyl-2,5-dihydro-1,2,3-triazine is reported.

AB - The reaction of substituted 1,2,3-triazole 1-oxides with dialkyl acetylenedicarboxylate dipolarophiles gave a new route to monocyclic 1,2,3-triazine derivatives via a multi-step sequence of cycloaddition, sigmatropic rearrangements, and ring expansion. With N-phenylmaleimide as dipolarophile, derivatives of a new tetrahydrofuro[2,3-d]-1,2,3-triazole system were formed. Mechanisms are discussed. An X-ray crystal structure of 2-(p-bromophenyl)-5-methoxalyl-5-methoxycarbonyl-4,6-dimethyl-2,5-dihydro-1,2,3-triazine is reported.

M3 - Article

JO - Journal Of The Chemical Society-Perkin Transactions 1

JF - Journal Of The Chemical Society-Perkin Transactions 1

ER -