Stereoselective synthesis of (2E) 3-amino-2-(1H-benzimidazol-2-yl)acrylate and symmetric bisacrylates by transamination reactions

✍ Scribed by Richard Brugidou; Jean Pierre Bazureau; Jack Hamelin; Zohra Dahmani; Mustapha Rahmouni

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 214 KB
• Volume: 10
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1999)10:6<446::aid-hc2>3.0.co;2-e

✦ Synopsis

A range of various amines 2(a-i) was tested in transamination reactions using ethyl 2-(1Hbenzimidazol-2-yl)-3-dimethylamino-acrylate 1a. The (E)-s-cis/trans conformation of some representative products 4 was analyzed by 1 H and 13 C NMR spectra. The C-2/C-3 bond of the compounds 3(a-i) is strongly polarized by a push-pull effect. In the same manner, reactions of ethyl 2-(benzoxazol-2-yl)-3-dimethylamino-acrylate 1c with 1,4-diaminobenzene 2i, ethylenediamine 2i, and 1,5-diaminomaphthalene 2k have been investigated and gave directly the corresponding symmetric bis-acrylates 4(a-c) in good yields. ᭧ 1999