Chemistry and Chemical Biology ETDs

Publication Date

6-26-1972

Abstract

The current interest in the biological activity of certain 1 ,4-disubstituted pyrido[2 ,3-d]pyridazines prompted the investigation of various derivatives of the isomeric pyrido[3,4-d]pyridazine ring system. Thus, 1,4 ­ dichloro[3,4-d]pyridazine was treated with thiourea and the intermediate thiouronium salt hydrolyzed to give pyrido[3, 4-d]pyridazine-1,4(2H,3H)-dithione which was subsequently alkylated to give 1,4-bis(alkylthio)pyrido­[3,4-d]pyridazines. On the other hand, 1,4-bis(arylthio)­pyrido[3,4-d]pyridazines were prepared by the reaction of 1,4-dichloropyrido[3,4-d]pyridazine with various substituted thiophenols. Furthermore, treatment of 1,4-dichloropyrido[3,4-d]­pyridazine with a variety of substituted anilines gave the corresponding 1,4-disubstituted aniline derivatives, whereas reaction with alkylamines afforded only the 1(4)-chloro-4(1)-alkylaminopyrido[3,4-d]pyridazines. When 1-chloropyrido[3,4-d]pyridazine-4(3H)-one or 4-chloropyrido[3,4-d]pyridazine-1(2H)-one was treated with hydrazine, the corresponding 1-hydrazinopyrido[3,4-d]­pyridazine-4(3H)-one or 4-hydrazinopyrido[3,4-d]pyridazine 1(2H)-one was obtained. Subsequent cyclization of these compounds with nitrous acid yielded 6-hydroxypyrido[4,3-d]-tetrazolo[1,5-b]pyridazine and 6-hydroxypyrido[3,4-d]-tetrazolo[1,5-b]pyridazine, respectively, while treatment with diethoxymethyl acetate afforded 6-hydroxypyrido[4,3-d]-s-triazolo[4,3-b]pyridazine and 6-hydroxypyrido[3,4-d]-s­triazolo[4,3-b]pyridazine, accordingly.

Language

English

Document Type

Thesis

Degree Name

Chemistry

Level of Degree

Masters

Department Name

Department of Chemistry and Chemical Biology

First Committee Member (Chair)

Raymond N. Castle

Second Committee Member

Guido Herman Daub

Third Committee Member

David Lee Vander Jagt

Fourth Committee Member

Eleftherios Paul Papadopoulos

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