Diphenyl cyanocarbonimide

A similar sequence of reactions occurs with diphenyl cyanocarbonimidate (127). Sequential reaction of (127) with aniline and hydrazine gave 3-amino-5-phenylaminotriazole (Scheme 23) <82JHC1205, 87JHC275). With amino acids as the first nucleophile, more complex triazoles can be formed <93T165>. 

Besides being a key starting material for the preparation of polyorthocarbonates, dichlorodiphenoxy methane is a versatile synthon for the construction of heterocyclic systems of medicinal interest (Ref. 36). Its condensation with cyanamide affords diphenyl cyanocarbonimidate in high yield (Ref. 35) as shown in scheme 38 ... 

Scheme 38 Preparation of diphenyl cyanocarbonimidate from dichloro diphe-noxy methane.

The synthesis of diaryl-1,3i5-triazines 10, a new class of potent non-nucleoside reverse transcriptase inhibitors (NNRTIs) has been reported. The requisite amidines 8 were readily prepared from the corresponding phenylacelonitrilcs, while the isourea partners 9 were obtained in modest yields by the reaction of diphenyl cyanocarbonimidate with the appropriate aniline <01BMCL2229>. 

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