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Synfacts 2008(1): 0017-0017  
DOI: 10.1055/s-2007-991462
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Imidazo[1,2-c]quinazolines from Isothiocyanatobenzonitriles

Contributor(s): Victor Snieckus, Jignesh J. Patel
A. Bodtke, W.-D. Pfeiffer, H. Görls, H. Dollinger, P. Langer*
Universität Greifswald, Universität Jena, Boehringer Ingelheim Pharma GmbH & Co. KG, Biberach/Riss, Universität Rostock and Leibniz-Institut für Katalyse an der Universität Rostock e.V., Germany
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

Substituted 5-thioxo- and 5-oxo-6H-imidazo[1,2-c]quinazolines were synthesized by treatment of various functionalized α-aminoketones with 2-isothiocyanatobenzonitriles and 2-isocyanatobenzonitrile. Compound C (X = S) was further transformed to D by simple S-alkylation and the latter was subsequently converted into 1,2,4-triazolo[4,3-a]-imidazo[1,2-c]quinazolines E. All cyclizations proceeded well with good regioselectivity and in good yields.