1,2,3-TRIAZOLIUM-1-OXIDE, -1-IMIDE AND 1-METHANIDE HETERO-1,3,5-TRIENE EQUILIBRIUM - ABINITIO CALCULATIONS - A NEW BASE INDUCED RING EXPANSION OF 1-ALKYL-1,2,3-TRIAZOLIUM SALTS TO 2,3-DIHYDRO-1,2,4-TRIAZINES AND 1-AMINOIMIDAZOLES VIA THE 1,2,5-TRIAZAHEXA-1,3,5-TRIENE SYSTEM - AZOLIUM 1,3-DIPOLES

Patrick Mcardle

1,2,3-TRIAZOLIUM-1-OXIDE, -1-IMIDE AND 1-METHANIDE HETERO-1,3,5-TRIENE EQUILIBRIUM - ABINITIO CALCULATIONS - A NEW BASE INDUCED RING EXPANSION OF 1-ALKYL-1,2,3-TRIAZOLIUM SALTS TO 2,3-DIHYDRO-1,2,4-TRIAZINES AND 1-AMINOIMIDAZOLES VIA THE 1,2,5-TRIAZAHEXA-1,3,5-TRIENE SYSTEM - AZOLIUM 1,3-DIPOLES

Patrick Mcardle

Cellular & Molecular Medicine

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

Abstract

Treatment of substituted 1-methyl- and 1-trimethylsilylmethyl-1,2,3-triazolium salts with ethoxide and caesium fluoride respectively gave substituted 2,3-dihydro-1,2,4-triazines and 1-aminoimidazoles via 1,2,5-triazahexa-1,3,5-triene intermediates. Expected isomeric 1,2,3-triazolium-1-methanide 1,3-dipoles were not detected and ab initio calculations suggested that they are thermodynamically unfavoured. Ab initio calculations on the equilibrium between the acyclic hetero-1,3,5-triene system and the cyclic forms of 1,2,3-triazolium-1-oxide, -1-imide and -1-methanide are reported. X-ray crystal structures are described for 2,5,6-triphenyl-2,3-dihydro-1,2,4-triazine 6a and 1-(p-nitroanilino)-4,5-diphenylimidazole 11c.

Original language	English (Ireland)
Number of pages	6
Journal	Journal Of The Chemical Society-Perkin Transactions 1
Publication status	Published - 1 Jan 1992

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

Authors
BUTLER, RN,DUFFY, JP,CUNNINGHAM, D,MCARDLE, P,BURKE, LA

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Mcardle, P. (1992). 1,2,3-TRIAZOLIUM-1-OXIDE, -1-IMIDE AND 1-METHANIDE HETERO-1,3,5-TRIENE EQUILIBRIUM - ABINITIO CALCULATIONS - A NEW BASE INDUCED RING EXPANSION OF 1-ALKYL-1,2,3-TRIAZOLIUM SALTS TO 2,3-DIHYDRO-1,2,4-TRIAZINES AND 1-AMINOIMIDAZOLES VIA THE 1,2,5-TRIAZAHEXA-1,3,5-TRIENE SYSTEM - AZOLIUM 1,3-DIPOLES. Journal Of The Chemical Society-Perkin Transactions 1.

Mcardle, Patrick. / 1,2,3-TRIAZOLIUM-1-OXIDE, -1-IMIDE AND 1-METHANIDE HETERO-1,3,5-TRIENE EQUILIBRIUM - ABINITIO CALCULATIONS - A NEW BASE INDUCED RING EXPANSION OF 1-ALKYL-1,2,3-TRIAZOLIUM SALTS TO 2,3-DIHYDRO-1,2,4-TRIAZINES AND 1-AMINOIMIDAZOLES VIA THE 1,2,5-TRIAZAHEXA-1,3,5-TRIENE SYSTEM - AZOLIUM 1,3-DIPOLES. In: Journal Of The Chemical Society-Perkin Transactions 1. 1992.

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title = "1,2,3-TRIAZOLIUM-1-OXIDE, -1-IMIDE AND 1-METHANIDE HETERO-1,3,5-TRIENE EQUILIBRIUM - ABINITIO CALCULATIONS - A NEW BASE INDUCED RING EXPANSION OF 1-ALKYL-1,2,3-TRIAZOLIUM SALTS TO 2,3-DIHYDRO-1,2,4-TRIAZINES AND 1-AMINOIMIDAZOLES VIA THE 1,2,5-TRIAZAHEXA-1,3,5-TRIENE SYSTEM - AZOLIUM 1,3-DIPOLES",

abstract = "Treatment of substituted 1-methyl- and 1-trimethylsilylmethyl-1,2,3-triazolium salts with ethoxide and caesium fluoride respectively gave substituted 2,3-dihydro-1,2,4-triazines and 1-aminoimidazoles via 1,2,5-triazahexa-1,3,5-triene intermediates. Expected isomeric 1,2,3-triazolium-1-methanide 1,3-dipoles were not detected and ab initio calculations suggested that they are thermodynamically unfavoured. Ab initio calculations on the equilibrium between the acyclic hetero-1,3,5-triene system and the cyclic forms of 1,2,3-triazolium-1-oxide, -1-imide and -1-methanide are reported. X-ray crystal structures are described for 2,5,6-triphenyl-2,3-dihydro-1,2,4-triazine 6a and 1-(p-nitroanilino)-4,5-diphenylimidazole 11c.",

author = "Patrick Mcardle",

year = "1992",

month = jan,

day = "1",

language = "English (Ireland)",

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

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Mcardle, P 1992, '1,2,3-TRIAZOLIUM-1-OXIDE, -1-IMIDE AND 1-METHANIDE HETERO-1,3,5-TRIENE EQUILIBRIUM - ABINITIO CALCULATIONS - A NEW BASE INDUCED RING EXPANSION OF 1-ALKYL-1,2,3-TRIAZOLIUM SALTS TO 2,3-DIHYDRO-1,2,4-TRIAZINES AND 1-AMINOIMIDAZOLES VIA THE 1,2,5-TRIAZAHEXA-1,3,5-TRIENE SYSTEM - AZOLIUM 1,3-DIPOLES', Journal Of The Chemical Society-Perkin Transactions 1.

1,2,3-TRIAZOLIUM-1-OXIDE, -1-IMIDE AND 1-METHANIDE HETERO-1,3,5-TRIENE EQUILIBRIUM - ABINITIO CALCULATIONS - A NEW BASE INDUCED RING EXPANSION OF 1-ALKYL-1,2,3-TRIAZOLIUM SALTS TO 2,3-DIHYDRO-1,2,4-TRIAZINES AND 1-AMINOIMIDAZOLES VIA THE 1,2,5-TRIAZAHEXA-1,3,5-TRIENE SYSTEM - AZOLIUM 1,3-DIPOLES. / Mcardle, Patrick.
In: Journal Of The Chemical Society-Perkin Transactions 1, 01.01.1992.

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

TY - JOUR

T1 - 1,2,3-TRIAZOLIUM-1-OXIDE, -1-IMIDE AND 1-METHANIDE HETERO-1,3,5-TRIENE EQUILIBRIUM - ABINITIO CALCULATIONS - A NEW BASE INDUCED RING EXPANSION OF 1-ALKYL-1,2,3-TRIAZOLIUM SALTS TO 2,3-DIHYDRO-1,2,4-TRIAZINES AND 1-AMINOIMIDAZOLES VIA THE 1,2,5-TRIAZAHEXA-1,3,5-TRIENE SYSTEM - AZOLIUM 1,3-DIPOLES

AU - Mcardle, Patrick

PY - 1992/1/1

Y1 - 1992/1/1

N2 - Treatment of substituted 1-methyl- and 1-trimethylsilylmethyl-1,2,3-triazolium salts with ethoxide and caesium fluoride respectively gave substituted 2,3-dihydro-1,2,4-triazines and 1-aminoimidazoles via 1,2,5-triazahexa-1,3,5-triene intermediates. Expected isomeric 1,2,3-triazolium-1-methanide 1,3-dipoles were not detected and ab initio calculations suggested that they are thermodynamically unfavoured. Ab initio calculations on the equilibrium between the acyclic hetero-1,3,5-triene system and the cyclic forms of 1,2,3-triazolium-1-oxide, -1-imide and -1-methanide are reported. X-ray crystal structures are described for 2,5,6-triphenyl-2,3-dihydro-1,2,4-triazine 6a and 1-(p-nitroanilino)-4,5-diphenylimidazole 11c.

AB - Treatment of substituted 1-methyl- and 1-trimethylsilylmethyl-1,2,3-triazolium salts with ethoxide and caesium fluoride respectively gave substituted 2,3-dihydro-1,2,4-triazines and 1-aminoimidazoles via 1,2,5-triazahexa-1,3,5-triene intermediates. Expected isomeric 1,2,3-triazolium-1-methanide 1,3-dipoles were not detected and ab initio calculations suggested that they are thermodynamically unfavoured. Ab initio calculations on the equilibrium between the acyclic hetero-1,3,5-triene system and the cyclic forms of 1,2,3-triazolium-1-oxide, -1-imide and -1-methanide are reported. X-ray crystal structures are described for 2,5,6-triphenyl-2,3-dihydro-1,2,4-triazine 6a and 1-(p-nitroanilino)-4,5-diphenylimidazole 11c.

M3 - Article

JO - Journal Of The Chemical Society-Perkin Transactions 1

JF - Journal Of The Chemical Society-Perkin Transactions 1

ER -

Mcardle P. 1,2,3-TRIAZOLIUM-1-OXIDE, -1-IMIDE AND 1-METHANIDE HETERO-1,3,5-TRIENE EQUILIBRIUM - ABINITIO CALCULATIONS - A NEW BASE INDUCED RING EXPANSION OF 1-ALKYL-1,2,3-TRIAZOLIUM SALTS TO 2,3-DIHYDRO-1,2,4-TRIAZINES AND 1-AMINOIMIDAZOLES VIA THE 1,2,5-TRIAZAHEXA-1,3,5-TRIENE SYSTEM - AZOLIUM 1,3-DIPOLES. Journal Of The Chemical Society-Perkin Transactions 1. 1992 Jan 1.