Safe and Reliable Synthesis of Diazoketones and Quinoxalines in a Continuous Flow Reactor

A flow method for the synthesis of aliphatic and aromatic diazoketones from acyl chloride precursors has been developed and used to prepare quinoxalines in a multistep sequence without isolation of the potentially explosive diazoketone. The protocol showcases an efficient in-line purification using...

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Bibliographic Details
Published in:Organic letters 2011-01, Vol.13 (2), p.320-323
Main Authors: Martin, Laetitia J, Marzinzik, Andreas L, Ley, Steven V, Baxendale, Ian R
Format: Article
Language:English
Subjects:
Chemistry, Organic - instrumentation
Chemistry, Organic - methods
Diazonium Compounds - chemical synthesis
Diazonium Compounds - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Phenylenediamines - toxicity
Quinoxalines - chemical synthesis
Quinoxalines - chemistry
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Summary:A flow method for the synthesis of aliphatic and aromatic diazoketones from acyl chloride precursors has been developed and used to prepare quinoxalines in a multistep sequence without isolation of the potentially explosive diazoketone. The protocol showcases an efficient in-line purification using supported scavengers with time-saving and safety benefits and in particular a reduction in the operator’s exposure to carcinogenic phenylenediamines.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1027927