Synthesis of pyrrolo- and pyrido-[1,2-α]benzimidazolequinone anti-tumor agents containing a fused cyclopropane ring

John O'Shaughnessy; Fawaz Aldabbagh

doi:10.1055/s-2005-861832

Synthesis of pyrrolo- and pyrido-[1,2-α]benzimidazolequinone anti-tumor agents containing a fused cyclopropane ring

John O'Shaughnessy
, Fawaz Aldabbagh

National University of Ireland

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

Abstract

A cyclopropane ring has been fused onto tetrahydropyrrolo- and tetrahydropyrido-[1,2-a]-benzimidazoles and -benzimidazolequinones via the cycloaddition of diazomethines generated from the thermolysis of N-(allyl and but-3-enyl)benzimidazole-2-Eschenmoser hydrazones (aziridinyl imines). At lower temperatures, the 1,3-dipolar [3 + 2] cycloadduct was obtained for only the N-allylbenzimidazole-2-Eschenmoser hydrazones.

Original language	English
Pages (from-to)	1069-1076
Number of pages	8
Journal	Synthesis
Issue number	7
Early online date	21 Feb 2005
DOIs	https://doi.org/10.1055/s-2005-861832
Publication status	Published - 2 May 2005
Externally published	Yes

Keywords

Benzimidazoles
Bioreductive
Diazo-compounds
Heterocycles
Hydrazones

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title = "Synthesis of pyrrolo- and pyrido-[1,2-α]benzimidazolequinone anti-tumor agents containing a fused cyclopropane ring",

abstract = "A cyclopropane ring has been fused onto tetrahydropyrrolo- and tetrahydropyrido-[1,2-a]-benzimidazoles and -benzimidazolequinones via the cycloaddition of diazomethines generated from the thermolysis of N-(allyl and but-3-enyl)benzimidazole-2-Eschenmoser hydrazones (aziridinyl imines). At lower temperatures, the 1,3-dipolar [3 + 2] cycloadduct was obtained for only the N-allylbenzimidazole-2-Eschenmoser hydrazones.",

keywords = "Benzimidazoles, Bioreductive, Diazo-compounds, Heterocycles, Hydrazones",

author = "John O'Shaughnessy and Fawaz Aldabbagh",

year = "2005",

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day = "2",

doi = "10.1055/s-2005-861832",

language = "English",

pages = "1069--1076",

journal = "Synthesis",

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TY - JOUR

T1 - Synthesis of pyrrolo- and pyrido-[1,2-α]benzimidazolequinone anti-tumor agents containing a fused cyclopropane ring

AU - O'Shaughnessy, John

AU - Aldabbagh, Fawaz

PY - 2005/5/2

Y1 - 2005/5/2

N2 - A cyclopropane ring has been fused onto tetrahydropyrrolo- and tetrahydropyrido-[1,2-a]-benzimidazoles and -benzimidazolequinones via the cycloaddition of diazomethines generated from the thermolysis of N-(allyl and but-3-enyl)benzimidazole-2-Eschenmoser hydrazones (aziridinyl imines). At lower temperatures, the 1,3-dipolar [3 + 2] cycloadduct was obtained for only the N-allylbenzimidazole-2-Eschenmoser hydrazones.

AB - A cyclopropane ring has been fused onto tetrahydropyrrolo- and tetrahydropyrido-[1,2-a]-benzimidazoles and -benzimidazolequinones via the cycloaddition of diazomethines generated from the thermolysis of N-(allyl and but-3-enyl)benzimidazole-2-Eschenmoser hydrazones (aziridinyl imines). At lower temperatures, the 1,3-dipolar [3 + 2] cycloadduct was obtained for only the N-allylbenzimidazole-2-Eschenmoser hydrazones.

KW - Benzimidazoles

KW - Bioreductive

KW - Diazo-compounds

KW - Heterocycles

KW - Hydrazones

U2 - 10.1055/s-2005-861832

DO - 10.1055/s-2005-861832

M3 - Article

AN - SCOPUS:18744382820

SN - 0039-7881

SP - 1069

EP - 1076

JO - Synthesis

JF - Synthesis

IS - 7

ER -

Synthesis of pyrrolo- and pyrido-[1,2-α]benzimidazolequinone anti-tumor agents containing a fused cyclopropane ring

Abstract

Keywords

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