Solid phase synthesis of cyanoacetamidines: Fast access to potential bioisosteres of acceptor-substituted guanidines

✍ Scribed by Florencio Zaragoza

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 192 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01694-8

✦ Synopsis

A synthesis of cyanoacetamidines has been developed, which can be realized on solid support. Reaction of resin-bound cyanoacetic acid with aromatic isothiocyanates yielded thioamides, which could be condensed with primary or secondary aliphatic or aromatic amines in the presence of EDC to yield ketene aminals. TFA-mediated cleavage from the support with concomitant decarboxylation gave cyanoacetamidine trifluoroacetates in purities up to 83% (HPLC, 254 nm).