Stereochemical Aspects during Substitution Reaction of c-4-Bromo-r-1-cyano-c-3-methoxy-1,2,3,4-tetrahydroisoquinoline Derivatives with Amines

doi:10.1248/CPB.45.1414

Paper

Stereochemical Aspects during Substitution Reaction of c-4-Bromo-r-1-cyano-c-3-methoxy-1,2,3,4-tetrahydroisoquinoline Derivatives with Amines

Published Sep 15, 1997 · M. Sugiura, K. Asai, Y. Hamada

Chemical & Pharmaceutical Bulletin

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2

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Abstract

2-Acyl (or sulfonyl)-c-4-bromo-r-1-cyano-t-3-methoxy-1, 2, 3, 4-tetrahydroisoquinolines treated with primary or secondary amines are stereoselectively converted into 4-amino-1, 2, 3, 4-tetrahydroisoquinoline derivatives in high yields. The 1, 4-trans and 3, 4-trans configuration of the products has been determined by X-ray crystallography. The formation of an isoquinoline o-quinone type compound 5 is suggested as an intermediate in the reaction process.

Study Snapshot

This study demonstrates a high-yield stereoselective conversion of 2-Acyl-c-4-bromo-r-1-cyano-t-3-methoxy-1,2,3,4-tetrahydroisoquinolines with primary or secondary amines, resulting in 4-

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Stereochemical Aspects during Substitution Reaction of c-4-Bromo-r-1-cyano-c-3-methoxy-1,2,3,4-tetrahydroisoquinoline Derivatives with Amines

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