Reactivity of the Pyrimidine Nitrogen Atom toward an Acetal Moiety: Formation­ of 3-Ethoxy-2,3-dihydroimidazo[1,2-c]pyrimidines by Intramolecular Cyclization of N-(2,2-Diethoxyethyl)pyrimidine-4-amines

Robertas Juskenas; Viktoras Masevicius; Sigitas Tumkevicius

doi:10.1055/s-0033-1339350

Synthesis, Table of Contents

Synthesis 2013; 45(17): 2438-2446
DOI: 10.1055/s-0033-1339350

paper

Reactivity of the Pyrimidine Nitrogen Atom toward an Acetal Moiety: Formation of 3-Ethoxy-2,3-dihydroimidazo[1,2-c]pyrimidines by Intramolecular Cyclization of N-(2,2-Diethoxyethyl)pyrimidine-4-amines

Robertas Juskenas

Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, Lithuania Fax: +370(5)2330987 Email: sigitas.tumkevicius@chf.vu.lt

,

Viktoras Masevicius

Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, Lithuania Fax: +370(5)2330987 Email: sigitas.tumkevicius@chf.vu.lt

,

Sigitas Tumkevicius*

Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, Lithuania Fax: +370(5)2330987 Email: sigitas.tumkevicius@chf.vu.lt

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Abstract

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Abstract

A new protocol was developed for the synthesis of 2,3-dihydroimidazo[1,2-c]pyrimidines, based on an intramolecular reaction between a pyrimidine nitrogen atom and an acetal moiety in the presence of boron trifluoride etherate. The method was expanded to permit the synthesis of the triheterocyclic imidazo[1,2-c]pyrazolo[4,3-e]pyrimidine system.

Key words

acetals - cyclizations - heterocycles - polycycles - pyrimidines - imidazoles

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References

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Supplementary Material

Supporting Information

Reactivity of the Pyrimidine Nitrogen Atom toward an Acetal Moiety: Formation­ of 3-Ethoxy-2,3-dihydroimidazo[1,2-c]pyrimidines by Intramolecular Cyclization of N-(2,2-Diethoxyethyl)pyrimidine-4-amines

Reactivity of the Pyrimidine Nitrogen Atom toward an Acetal Moiety: Formation of 3-Ethoxy-2,3-dihydroimidazo[1,2-c]pyrimidines by Intramolecular Cyclization of N-(2,2-Diethoxyethyl)pyrimidine-4-amines