Chemistry and Chemical Biology ETDs

David B. Cox

Publication Date

5-20-1953

Abstract

Recent work by Castle and Kruse (16) has partially elucidated the range of reactivity of the chlorine atom in the compounds 4-chlorocinnoline and 4-chloro-6,7-dimethoxycinnoline. Condensations between the chlorinated cinnolines and certain phenylacetonitriles were found to proceed readily; however, condensations with compounds of the malonic ester type were unsuccessful. It was found that hydrolysis of the condensation product obtained from 4-chlorocinnoline and phenylacetontrile by hot 60% sulfuric acid caused decarboxylation of the intermediate acid, the final product being 4-benzylcinnoline. This compound has a formal resemblance to the basic ring structure of papaverine.

Project Sponsors

Upjohn Company

Language

English

Document Type

Dissertation

Degree Name

Chemistry

Level of Degree

Doctoral

Department Name

Department of Chemistry and Chemical Biology

First Committee Member (Chair)

Raymond N. Castle

Second Committee Member

Ernest Lynne Martin

Third Committee Member

Richard LeRoy Ferm

Fourth Committee Member

Guido Herman Daub

Fifth Committee Member

Jesse LeRoy Riebsomer

Sixth Committee Member

Milton Kahn

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