A Unified Approach to the Isomeric α-, β-, γ-, and δ-Carbolines via their 6,7,8,9-Tetrahydro Counterparts

Qiao Yan; Emma Gin; Martin G. Banwell; Anthony C. Willis; Paul D. Carr

doi:10.1021/acs.joc.7b00323

A Unified Approach to the Isomeric α-, β-, γ-, and δ-Carbolines via their 6,7,8,9-Tetrahydro Counterparts

Qiao Yan, Emma Gin, Martin G. Banwell^*, Anthony C. Willis, Paul D. Carr

^*Corresponding author for this work

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

50 Citations (Scopus)

Abstract

A cross-coupling/reductive cyclization protocol has been employed in a unified approach to all four carbolines. So, for example, the 2-nitropyridine 8, which is readily prepared through an efficient palladium-catalyzed Ullmann cross-coupling reaction, is reductively cyclized under conventional conditions to give 6,7,8,9-tetrahydro-α-carboline that is itself readily aromatized to give α-carboline (1).

Original language	English
Pages (from-to)	4328-4335
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	82
Issue number	8
DOIs	https://doi.org/10.1021/acs.joc.7b00323
Publication status	Published - 21 Apr 2017

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abstract = "A cross-coupling/reductive cyclization protocol has been employed in a unified approach to all four carbolines. So, for example, the 2-nitropyridine 8, which is readily prepared through an efficient palladium-catalyzed Ullmann cross-coupling reaction, is reductively cyclized under conventional conditions to give 6,7,8,9-tetrahydro-α-carboline that is itself readily aromatized to give α-carboline (1).",

author = "Qiao Yan and Emma Gin and Banwell, \{Martin G.\} and Willis, \{Anthony C.\} and Carr, \{Paul D.\}",

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AU - Willis, Anthony C.

AU - Carr, Paul D.

PY - 2017/4/21

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AB - A cross-coupling/reductive cyclization protocol has been employed in a unified approach to all four carbolines. So, for example, the 2-nitropyridine 8, which is readily prepared through an efficient palladium-catalyzed Ullmann cross-coupling reaction, is reductively cyclized under conventional conditions to give 6,7,8,9-tetrahydro-α-carboline that is itself readily aromatized to give α-carboline (1).

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A Unified Approach to the Isomeric α-, β-, γ-, and δ-Carbolines via their 6,7,8,9-Tetrahydro Counterparts

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