Process for producing 1-substituted tetrahydroquinazolines

Details Process for producing 1-substituted tetrahydroquinazolines Process for producing 1-substituted tetrahydroquinazolines

C - Chemistry, Metallurgy

07

D

C07D 239/96 (2006.01) C07D 401/06 (2006.01) C07D 403/02 (2006.01)

Patent

CA 2190236

A process for producing 1-substituted tetrahydroquinazolines represented by the formula (III): Image (III) wherein Z represents a methylene group which is optionally substituted by an alkyl group; R6 represents an alkyl group or an aralkyl group; R1 and R2 independently represent a hydrogen atom, a halogen atom, a nitro group, an azido group, an alkyl group, an alkenyl group, an aralkyl group, an alkoxy groupm, an alkoxycarbonyl group, an acyloxy group, or an amino group represented by XNR4R5 in which X represents a direct bond, an alkylene group or a carbonyl group, and N, R4 and R5 may form together a five- or six-membered heterocyclic ring or R4 and R5 independently represent an alkyl group or an acyloxy alkyl group; and R3 represents a hydrogen atom, a halogen atom, a nitro group, an azido group, an alkyl group, an alkenyl group, an aralkyl group, an alkoxy group, or an alkoxycarbonyl group which comprises reacting tetrahydroquinazolines represented by the formula (I): Image (I) wherein R1, R2 and R3 are as defined above with hexamethyldisilazane; and reacting the resultant product with a chloroalkanoate represented by the formula (II): Cl-Z-CO-O-R6 (II) wherein Z and R6 are as defined above in the presence of an iodide of an alkaline metal, followed by desilylation.

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