Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine

Readily synthesized biphenyl-2-carbaldehyde O-acetyl oximes were exposed to UV radiation affording phenanthridines. The scope and limitations of this novel reaction were explored. For example, exposure of 2',3'-dimethoxy-[1,1'-biphenyl]-2-carbaldehyde O-acetyl oxime to UV radiation af...

Full description

Bibliographic Details
Main Authors:	Songeziwe Ntsimango, Kennedy J. Ngwira, Moira L. Bode, Charles B. de Koning
Format:	Article
Language:	English
Published:	Beilstein-Institut 2021-09-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	aromatic compounds cyclization iminyl radical phenanthridines radical cation synthesis uv irradiation
Online Access:	https://doi.org/10.3762/bjoc.17.152

id	doaj-a119e24540a846ba84887db34c070298
record_format	Article
spelling	doaj-a119e24540a846ba84887db34c0702982021-09-13T09:24:29ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-09-011712340234710.3762/bjoc.17.1521860-5397-17-152Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridineSongeziwe Ntsimango0Kennedy J. Ngwira1Moira L. Bode2Charles B. de Koning3Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South AfricaMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South AfricaMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South AfricaMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South AfricaReadily synthesized biphenyl-2-carbaldehyde O-acetyl oximes were exposed to UV radiation affording phenanthridines. The scope and limitations of this novel reaction were explored. For example, exposure of 2',3'-dimethoxy-[1,1'-biphenyl]-2-carbaldehyde O-acetyl oxime to UV radiation afforded 4-methoxyphenanthridine in 54% yield. This methodology was applied to the synthesis of trisphaeridine to afford the product in four linear steps in an overall yield of 6.5% from 1-bromo-2,4,5-trimethoxybenzene.https://doi.org/10.3762/bjoc.17.152aromatic compoundscyclizationiminyl radicalphenanthridinesradical cationsynthesisuv irradiation
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Songeziwe Ntsimango Kennedy J. Ngwira Moira L. Bode Charles B. de Koning
spellingShingle	Songeziwe Ntsimango Kennedy J. Ngwira Moira L. Bode Charles B. de Koning Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine Beilstein Journal of Organic Chemistry aromatic compounds cyclization iminyl radical phenanthridines radical cation synthesis uv irradiation
author_facet	Songeziwe Ntsimango Kennedy J. Ngwira Moira L. Bode Charles B. de Koning
author_sort	Songeziwe Ntsimango
title	Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine
title_short	Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine
title_full	Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine
title_fullStr	Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine
title_full_unstemmed	Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine
title_sort	synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2021-09-01
description	Readily synthesized biphenyl-2-carbaldehyde O-acetyl oximes were exposed to UV radiation affording phenanthridines. The scope and limitations of this novel reaction were explored. For example, exposure of 2',3'-dimethoxy-[1,1'-biphenyl]-2-carbaldehyde O-acetyl oxime to UV radiation afforded 4-methoxyphenanthridine in 54% yield. This methodology was applied to the synthesis of trisphaeridine to afford the product in four linear steps in an overall yield of 6.5% from 1-bromo-2,4,5-trimethoxybenzene.
topic	aromatic compounds cyclization iminyl radical phenanthridines radical cation synthesis uv irradiation
url	https://doi.org/10.3762/bjoc.17.152
work_keys_str_mv	AT songeziwentsimango synthesisofphenanthridinesviaanovelphotochemicallymediatedcyclizationandapplicationtothesynthesisoftriphaeridine AT kennedyjngwira synthesisofphenanthridinesviaanovelphotochemicallymediatedcyclizationandapplicationtothesynthesisoftriphaeridine AT moiralbode synthesisofphenanthridinesviaanovelphotochemicallymediatedcyclizationandapplicationtothesynthesisoftriphaeridine AT charlesbdekoning synthesisofphenanthridinesviaanovelphotochemicallymediatedcyclizationandapplicationtothesynthesisoftriphaeridine
_version_	1717381121548746752

Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine

Similar Items