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A convenient synthesis of di- and trisubstituted 2-aminoimidazoles from 1-amidino-3-trityl-thioureas

✍ Scribed by Jitendra C. Kaila; Arshi B. Baraiya; Amit N. Pandya; Hitesh B. Jalani; Kamala K. Vasu; V. Sudarsanam

Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 388 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.04.083

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✦ Synopsis

a b s t r a c t Convenient synthesis of 2-amino-1,5-disubstituted and 2-amino-1,4,5-trisubstituted imidazoles has been reported using readily available starting materials and simple reagents under mild conditions. Guanylation of 1-amidino-3-trityl-thioureas 1 and 7 using mercury(II) chloride (Caution) as a thiophile resulted in corresponding guanidines 2 and 8 which on reaction with a-bromo ketones yielded 2-tritylaminoimidazoles. Deprotection of 2-tritylaminoimidazoles using trifluoroacetic acid at room temperature furnished desired 2-aminoimidazoles 4 and 10 in good to moderate yields.

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