Novel reaction of 3,4-dibromofuran with azo diesters to give tetrahydropyridazinones

Kati Marianne Aitken; Robert Alan Aitken; Alexandra Martha Zoya Slawin

doi:10.1039/C6RA02735K

Novel reaction of 3,4-dibromofuran with azo diesters to give tetrahydropyridazinones

Kati Marianne Aitken, Robert Alan Aitken, Alexandra Martha Zoya Slawin

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

Abstract

Cycloaddition of 3,4-dibromofuran with azo diesters proceeds by a Diels–Alder reaction followed by a novel rearrangement to give 3,5-dibromotetrahydropyridazin-4-ones. Variable-temperature NMR spectroscopy shows four separate conformations at low temperature attributed to restricted rotation about the carbamate functions. The ethyl compound decomposes upon storage with loss of the carbamate groups and aromatisation to give a simple bromohydroxypyridazinium salt.

Original language	English
Pages (from-to)	22969-22972
Number of pages	4
Journal	RSC Advances
Volume	6
DOIs	https://doi.org/10.1039/C6RA02735K
Publication status	Published - 29 Feb 2016

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Aitken_2016_RSCA_NovelAzoDiesters_CCBY
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title = "Novel reaction of 3,4-dibromofuran with azo diesters to give tetrahydropyridazinones",

abstract = "Cycloaddition of 3,4-dibromofuran with azo diesters proceeds by a Diels–Alder reaction followed by a novel rearrangement to give 3,5-dibromotetrahydropyridazin-4-ones. Variable-temperature NMR spectroscopy shows four separate conformations at low temperature attributed to restricted rotation about the carbamate functions. The ethyl compound decomposes upon storage with loss of the carbamate groups and aromatisation to give a simple bromohydroxypyridazinium salt.",

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T1 - Novel reaction of 3,4-dibromofuran with azo diesters to give tetrahydropyridazinones

AU - Aitken, Kati Marianne

AU - Aitken, Robert Alan

AU - Slawin, Alexandra Martha Zoya

PY - 2016/2/29

Y1 - 2016/2/29

N2 - Cycloaddition of 3,4-dibromofuran with azo diesters proceeds by a Diels–Alder reaction followed by a novel rearrangement to give 3,5-dibromotetrahydropyridazin-4-ones. Variable-temperature NMR spectroscopy shows four separate conformations at low temperature attributed to restricted rotation about the carbamate functions. The ethyl compound decomposes upon storage with loss of the carbamate groups and aromatisation to give a simple bromohydroxypyridazinium salt.

AB - Cycloaddition of 3,4-dibromofuran with azo diesters proceeds by a Diels–Alder reaction followed by a novel rearrangement to give 3,5-dibromotetrahydropyridazin-4-ones. Variable-temperature NMR spectroscopy shows four separate conformations at low temperature attributed to restricted rotation about the carbamate functions. The ethyl compound decomposes upon storage with loss of the carbamate groups and aromatisation to give a simple bromohydroxypyridazinium salt.

UR - http://www.rsc.org/suppdata/c6/ra/c6ra02735k/c6ra02735k1.pdf

UR - http://www.rsc.org/suppdata/c6/ra/c6ra02735k/c6ra02735k2.cif

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DO - 10.1039/C6RA02735K

M3 - Article

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VL - 6

SP - 22969

EP - 22972

JO - RSC Advances

JF - RSC Advances

ER -

Novel reaction of 3,4-dibromofuran with azo diesters to give tetrahydropyridazinones

Abstract

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