An efficient and mild conditions synthesis of 2-aza-1,3-dienes fromphospha-λ5-azenes.

✍ Scribed by José Barluenga; Miguel Ferrero; Francisco Palacios

• Book ID: 104216723
• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 140 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)80628-0

✦ Synopsis

Aza-Wittig reaction of N-acrylic phospha-x5-azenes with aldehydes gives 3-ethoxycarbonyl 2-aza-1,3-dienes in very high yields. Compounds containing the 2-aza-1,3-diene group represent a very important class of derivatives as a result of their potential as key intermediates in organic synthesis. Particularly significant is the Diels-Alder reactivity of these substances' for the construction of heterocycles. Previously, several procedures of synthesis 2-4 and some reactions of elec-'gH5 38 25 H2CC12 92 * Obtained from l_(R=Ph) except 3f from I(R=Me).

The synthesis described in this communication provides an easy entry to N-alkyliden and N-aryliden-aminoacrylic acid derivatives 3, making use of readly available starting materials and under mild reaction conditions. These systems could be key intermediates in the synthesis of new aminoacids derivatives l4 and six membered heterocycles 4 .