A 'push-pull' tropylium-fused aminoporphyrazine

Andrea Ruggiero; Matthew J. Fuchter; Okanya J. Kokas; Mihaela Negru; Andrew J.P. White; Peter R. Haycock; Brian M. Hoffman; Anthony G.M. Barrett

doi:10.1016/j.tet.2009.09.105

A 'push-pull' tropylium-fused aminoporphyrazine

Andrea Ruggiero, Matthew J. Fuchter, Okanya J. Kokas, Mihaela Negru, Andrew J.P. White, Peter R. Haycock, Brian M. Hoffman, Anthony G.M. Barrett^*

^*Corresponding author for this work

Chemistry

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

12 Scopus citations

Abstract

Crossover Linstead macrocyclization of cycloheptatrienylmaleonitrile and (dimethylamino)-maleonitrile gave access to an unsymmetrical (A₃B) porphyrazine bearing six peripheral amino substituents and a fused cycloheptatrienyl ring. Subsequent hydride abstraction gave a tropylium-fused aminoporphyrazine, which contains both strongly electron-donating and withdrawing groups and thus can be labelled as a 'push-pull' macrocycle. Detailed structural studies of this novel porphyrazine are described.

Original language	English (US)
Pages (from-to)	9690-9693
Number of pages	4
Journal	Tetrahedron
Volume	65
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2009.09.105
State	Published - Nov 21 2009

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2009.09.105

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@article{946e49fef38444b28d6418029ce1b5d0,

title = "A 'push-pull' tropylium-fused aminoporphyrazine",

abstract = "Crossover Linstead macrocyclization of cycloheptatrienylmaleonitrile and (dimethylamino)-maleonitrile gave access to an unsymmetrical (A3B) porphyrazine bearing six peripheral amino substituents and a fused cycloheptatrienyl ring. Subsequent hydride abstraction gave a tropylium-fused aminoporphyrazine, which contains both strongly electron-donating and withdrawing groups and thus can be labelled as a 'push-pull' macrocycle. Detailed structural studies of this novel porphyrazine are described.",

author = "Andrea Ruggiero and Fuchter, {Matthew J.} and Kokas, {Okanya J.} and Mihaela Negru and White, {Andrew J.P.} and Haycock, {Peter R.} and Hoffman, {Brian M.} and Barrett, {Anthony G.M.}",

note = "Funding Information: We thank GlaxoSmithKline for the generous endowment (to A.G.M.B.), the Wolfson Foundation for establishing the Wolfson Centre for Organic Chemistry in Medical Sciences at Imperial College, the Engineering and Physical Sciences Research Council and the National Science Foundation for generous support of our studies. ",

year = "2009",

month = nov,

day = "21",

doi = "10.1016/j.tet.2009.09.105",

language = "English (US)",

volume = "65",

pages = "9690--9693",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "47",

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TY - JOUR

T1 - A 'push-pull' tropylium-fused aminoporphyrazine

AU - Ruggiero, Andrea

AU - Fuchter, Matthew J.

AU - Kokas, Okanya J.

AU - Negru, Mihaela

AU - White, Andrew J.P.

AU - Haycock, Peter R.

AU - Hoffman, Brian M.

AU - Barrett, Anthony G.M.

N1 - Funding Information: We thank GlaxoSmithKline for the generous endowment (to A.G.M.B.), the Wolfson Foundation for establishing the Wolfson Centre for Organic Chemistry in Medical Sciences at Imperial College, the Engineering and Physical Sciences Research Council and the National Science Foundation for generous support of our studies.

PY - 2009/11/21

Y1 - 2009/11/21

N2 - Crossover Linstead macrocyclization of cycloheptatrienylmaleonitrile and (dimethylamino)-maleonitrile gave access to an unsymmetrical (A3B) porphyrazine bearing six peripheral amino substituents and a fused cycloheptatrienyl ring. Subsequent hydride abstraction gave a tropylium-fused aminoporphyrazine, which contains both strongly electron-donating and withdrawing groups and thus can be labelled as a 'push-pull' macrocycle. Detailed structural studies of this novel porphyrazine are described.

AB - Crossover Linstead macrocyclization of cycloheptatrienylmaleonitrile and (dimethylamino)-maleonitrile gave access to an unsymmetrical (A3B) porphyrazine bearing six peripheral amino substituents and a fused cycloheptatrienyl ring. Subsequent hydride abstraction gave a tropylium-fused aminoporphyrazine, which contains both strongly electron-donating and withdrawing groups and thus can be labelled as a 'push-pull' macrocycle. Detailed structural studies of this novel porphyrazine are described.

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U2 - 10.1016/j.tet.2009.09.105

DO - 10.1016/j.tet.2009.09.105

M3 - Article

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SN - 0040-4020

VL - 65

SP - 9690

EP - 9693

JO - Tetrahedron

JF - Tetrahedron

IS - 47

ER -

A 'push-pull' tropylium-fused aminoporphyrazine

Abstract

ASJC Scopus subject areas

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CCDC 737182: Experimental Crystal Structure Determination

CCDC 737183: Experimental Crystal Structure Determination

Cite this

A 'push-pull' tropylium-fused aminoporphyrazine

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 737182: Experimental Crystal Structure Determination

CCDC 737183: Experimental Crystal Structure Determination

Cite this