Synthesis of Azapyrrolo[3,2,1-jk]carbazoles, Azaindolo[3,2,1-jk]carbazoles, and Carbazole-1-carbonitriles by Gas-Phase Cyclization of Aryl Radicals

Lynne A. Crawford; Hamish McNab; Andrew R. Mount; Jeanne Verhille; Stuart I. Wharton

doi:10.1055/s-0029-1218634

Synthesis of Azapyrrolo[3,2,1-jk]carbazoles, Azaindolo[3,2,1-jk]carbazoles, and Carbazole-1-carbonitriles by Gas-Phase Cyclization of Aryl Radicals

Lynne A. Crawford, Hamish McNab, Andrew R. Mount, Jeanne Verhille, Stuart I. Wharton

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

Abstract

Flash vacuum pyrolysis of N-(2-nitroheteroaryl)indoles or -carbazoles at 875 degrees C gave aza analogues of strained pyrrolo[3,2,1-jk]carbazole (50-55%) and indolo[3,2,1-jk]carbazole (55-85%) ring systems, respectively, through generation of aryl radicals and cyclization. The corresponding reactions of N-(2-nitroheteroaryl)indazoles and -benzimidazoles at 850 degrees C, on the other hand, gave carbazole-1-carbonitrile derivatives (56-64%) by a mechanism involving radical ring opening and hydrogen atom rearrangement.

Original language	English
Pages (from-to)	923-928
Number of pages	6
Journal	Synthesis: Journal of Synthetic Organic Chemistry
Issue number	6
DOIs	https://doi.org/10.1055/s-0029-1218634
Publication status	Published - Mar 2010

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title = "Synthesis of Azapyrrolo[3,2,1-jk]carbazoles, Azaindolo[3,2,1-jk]carbazoles, and Carbazole-1-carbonitriles by Gas-Phase Cyclization of Aryl Radicals",

abstract = "Flash vacuum pyrolysis of N-(2-nitroheteroaryl)indoles or -carbazoles at 875 degrees C gave aza analogues of strained pyrrolo[3,2,1-jk]carbazole (50-55%) and indolo[3,2,1-jk]carbazole (55-85%) ring systems, respectively, through generation of aryl radicals and cyclization. The corresponding reactions of N-(2-nitroheteroaryl)indazoles and -benzimidazoles at 850 degrees C, on the other hand, gave carbazole-1-carbonitrile derivatives (56-64%) by a mechanism involving radical ring opening and hydrogen atom rearrangement.",

author = "Crawford, {Lynne A.} and Hamish McNab and Mount, {Andrew R.} and Jeanne Verhille and Wharton, {Stuart I.}",

year = "2010",

month = mar,

doi = "10.1055/s-0029-1218634",

language = "English",

pages = "923--928",

journal = "Synthesis: Journal of Synthetic Organic Chemistry",

issn = "0039-7881",

publisher = "Thieme Gruppe",

number = "6",

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TY - JOUR

T1 - Synthesis of Azapyrrolo[3,2,1-jk]carbazoles, Azaindolo[3,2,1-jk]carbazoles, and Carbazole-1-carbonitriles by Gas-Phase Cyclization of Aryl Radicals

AU - Crawford, Lynne A.

AU - McNab, Hamish

AU - Mount, Andrew R.

AU - Verhille, Jeanne

AU - Wharton, Stuart I.

PY - 2010/3

Y1 - 2010/3

N2 - Flash vacuum pyrolysis of N-(2-nitroheteroaryl)indoles or -carbazoles at 875 degrees C gave aza analogues of strained pyrrolo[3,2,1-jk]carbazole (50-55%) and indolo[3,2,1-jk]carbazole (55-85%) ring systems, respectively, through generation of aryl radicals and cyclization. The corresponding reactions of N-(2-nitroheteroaryl)indazoles and -benzimidazoles at 850 degrees C, on the other hand, gave carbazole-1-carbonitrile derivatives (56-64%) by a mechanism involving radical ring opening and hydrogen atom rearrangement.

AB - Flash vacuum pyrolysis of N-(2-nitroheteroaryl)indoles or -carbazoles at 875 degrees C gave aza analogues of strained pyrrolo[3,2,1-jk]carbazole (50-55%) and indolo[3,2,1-jk]carbazole (55-85%) ring systems, respectively, through generation of aryl radicals and cyclization. The corresponding reactions of N-(2-nitroheteroaryl)indazoles and -benzimidazoles at 850 degrees C, on the other hand, gave carbazole-1-carbonitrile derivatives (56-64%) by a mechanism involving radical ring opening and hydrogen atom rearrangement.

U2 - 10.1055/s-0029-1218634

DO - 10.1055/s-0029-1218634

M3 - Article

SN - 0039-7881

SP - 923

EP - 928

JO - Synthesis: Journal of Synthetic Organic Chemistry

JF - Synthesis: Journal of Synthetic Organic Chemistry

IS - 6

ER -

Synthesis of Azapyrrolo[3,2,1-jk]carbazoles, Azaindolo[3,2,1-jk]carbazoles, and Carbazole-1-carbonitriles by Gas-Phase Cyclization of Aryl Radicals

Abstract

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