Syntheses of N-Substituted Thymine Thioacetamides. A Novel Approach to Site Selective Acylation of Diaminoalkanes

Jaroslaw Spychala

doi:https://doi.org/10.1016/s0040-4020(00)00704-3

Syntheses of N-Substituted Thymine Thioacetamides. A Novel Approach to Site Selective Acylation of Diaminoalkanes

Abstract

A new series of N-substituted thiocarbamoyl derivs. contg. histamine, tryptamine, and other moieties having at least one amino group attached to an aliph. chain has been synthesized from (1-thyminyl)thioacetamide in good isolated yields (69-86%). N-[2-(4-Imidazolyl)ethyl](1-thyminyl)thioacetamide was hydrolyzed to its amide on prolonged heating in water. Ammonium sulfide (20-22% soln. in water) has found interesting new applications in the efficient synthesis of N-[2-(3-indolyl)ethyl](1-thyminyl)thioacetamide and site selective acylation of diaminoalkanes, starting directly from nitriles.

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Jaroslaw Spychala dr

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Category:: Magazine publication
Type:: Magazine publication
Published in:: TETRAHEDRON no. 56, edition 40, pages 7981 - 7986,
ISSN: 0040-4020
Publication year:: 2000
Bibliographic description:: Jaroslaw Spychala, Syntheses of N-Substituted Thymine Thioacetamides. A Novel Approach to Site Selective Acylation of Diaminoalkanes, Tetrahedron, vol. 56(40), pages 7981-7986, 2000.
DOI:: Digital Object Identifier (open in new tab) https://doi.org/10.1016/s0040-4020(00)00704-3
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