Chemistry and Chemical Biology ETDs

Babu George

Publication Date

3-28-1976

Abstract

When an N-ethoxycarbonylthioamide is treated with dinucleophi l ic reagents containing a primary or secondary amino group and another nucleophilic group, reaction occurs initially between the amino group of the reagent and the thiocarbonyl of the substrate with elimination of hydrogen sulfide and formation of a carbon, nitrogen double bond. The intermediate thus formed may subsequently cyclize in either of two different manners depending upon the relative positions of the two nucleophilic groups in the reagent.

A. If the second nucleophilic group is adjacent to the amino group, or separated from it by one carbon atom, cyclization involves nucleophilic attack at the carbonyl of the intermediate and elimination of ethanol. In this case a heterocyclic ring is formed which contains a carbonyl group and three heteroatoms (the two nucleophilic atoms of the reagent and the nitrogen atom of the substrate) at 1,2,4 or 1 ,3,5 relative positions. Thus, the reaction of N-ethoxycarbonylthioamides with the following dinucleophilic reagents yields the indicated products.

Language

English

Document Type

Dissertation

Degree Name

Chemistry

Level of Degree

Doctoral

Department Name

Department of Chemistry and Chemical Biology

First Committee Member (Chair)

Eleftherios Paul Papadopoulos

Second Committee Member

Guido Herman Daub

Third Committee Member

Robert Edwin Tapscott

Fourth Committee Member

David Lee Vander Jagt

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