Synthesis of Polysubstituted Isoquinolines and Related Fused Pyridines from Alkenyl Boronic Esters via a Copper-Catalyzed Azidation/Aza-Wittig Condensation Sequence

An efficient and straightforward synthesis of isoquinolines is reported from internal alkenyl boronic esters, easily prepared from the corresponding 1,2-bis­(boronates), via a sequential copper-catalyzed azidation/aza-Wittig condensation. This synthetic method has been used to synthesize quinisocain...

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Published inJournal of organic chemistry Vol. 83; no. 2; pp. 843 - 853
Main Authors Jayaram, Vankudoth, Sridhar, Tailor, Sharma, Gangavaram V. M, Berrée, Fabienne, Carboni, Bertrand
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.01.2018
Amer Chemical Soc
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
Organic chemistry
Physical Sciences
Science & Technology
TETRAHYDROISOQUINOLINE
PHENANTHRIDINES
LOCAL-ANESTHETICS
COMPLEXES
EFFICIENT SYNTHESIS
ARYL AZIDES
DERIVATIVES
DIBORATION
CYCLIZATION
DISCOVERY
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Summary:An efficient and straightforward synthesis of isoquinolines is reported from internal alkenyl boronic esters, easily prepared from the corresponding 1,2-bis­(boronates), via a sequential copper-catalyzed azidation/aza-Wittig condensation. This synthetic method has been used to synthesize quinisocaine, a topical anesthetic used for the treatment of pain and pruritus, and further extended to thieno­[2,3-c]­pyridines by using 2-thiophenecarboxaldehyde as coupling partner in the first step.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02831