The application of vinylogous iminium salts and related synthons to the preparation of monosubstituted triazolopyrimidines

Keywords

Vinylogous iminium (vinamidinium) salts, 3-chloropropeniminium salts, 3-amino-1, 2, 4-triazole reactions, Regioselective formation of 1, 4-triazolo[1, 5-a]pyrimidines, Three-carbon synthons in heterocycle synthesis

Abstract

The 6-substituted-1,2,4-triazolo[l,5-a)pyrimidines can be regiospecifically prepared via the reaction of 2-substituted vinamidinium salts with 3-amino-1,2,4-triazole under basic conditions. The 7-substituted-1,2,4-triazolo­ [1,5-a)pyrimidines can be regioslectively prepared via the reaction of 1-substituted vinamidinium salts and 3-substituted-3-chloropropeniminium salts with 3-amino-1,2,4-triazole under basic conditions. The reactions of 3-amino-1,2,4-triazole with unsymmetrical vinamidinium salts, chloropropeniminium salts and the other related three-carbon synthons were investigated under a variety of conditions. The best conditions to make 7-substituted triazolopyrimidines are with 3-substituted chloropropeniminium salts and 1-substituted vinamidinium salts under basic conditions.

Notes

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Graduation Date

1993

Semester

Summer

Advisor

Gupton, John T.

Degree

Master of Science (M.S.)

College

College of Arts and Sciences

Department

Chemistry

Format

PDF

Pages

146 pages

Language

English

Length of Campus-only Access

None

Access Status

Masters Thesis (Open Access)

Identifier

DP0028680

Subjects

Arts and Sciences -- Dissertations; Academic; Dissertations; Academic -- Arts and Sciences; Heterocyclic compounds--Synthesis; Pyrimidines--Synthesis; Triazoles; Organonitrogen compounds--Synthesis; Nitrilium salts

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