Synthesis and transformations of methyl (E)-2-(acetylamino)-3-cyanoprop-2-enoate und methyl (E)-2-(benzoylamino)-3-cyanoprop-2-enoate, versatile reagents for the preparation of polyfunctional heterocyclic systems

✍ Scribed by Lucija Pizzioli; Brina Ornik; Jurij Svete; Branko Stanovnik

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: German
• Weight: 329 KB
• Volume: 81
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19980810205

✦ Synopsis

Methyl (E)-2-(acetylamino)-3-cyanoprop-2-enoate (2a) and its 2-benzoyl analog 2b were prepared from the corresponding methyl (Z)-2-(acylamino)-3-(dimethylamino)propenoates 1. Multifunctional compounds 2 are versatile synthons for preparation of polysubstituted heterocyclic systems such as pyrroles 4, pyrimidines 5 and 6, pyridazines 7, pyrazoles 8, 9, and 11, and ~sox~zoles 10.

Introduction. ~ Derivatives of 2-amino-3-cyanoprop-2-enoates have been prepared from dichloromaleic anhydride [l] and by condensation of alkyl cyanoformates and analogous compounds with active methylene compounds [2-41. Inspite of the fact that these compounds have been described as precursors for the synthesis of a$-didehydro-aamino acids, reactions involving either CN or ester group have not been reported.