New efficient synthesis of pyrimido[1,6-c]quinazolin-4-ones by a Biginelli 3CC/Staudinger/aza-Wittig sequence

作者：Li, Wen-Jing; Liu, Shuai; He, Ping; Ding, Ming-Wu^*

来源：Tetrahedron, 2010, 66(41): 8151-8159.

DOI：10.1016/j.tet.2010.08.046

• ONE-POT SYNTHESIS
• ONE-STEP FUSION
• CONDENSATION REACTION
• IMPROVED PROTOCOL
• CHLORIDE
• DIHYDROPYRIMIDINONES
• 3-COMPONENT
• FACILE
• AZIDES

Dihydropyrimidinone azides 1, obtained from trimethylsilyl chloride-catalyzed Biginelli reaction of 2-azidobenzaldehyde, ethyl acetoacetate, and urea (or thiourea) at room temperature, reacted with triphenylphosphine to give iminophosphorane 2. A tandem aza-Wittig reaction of iminophosphorane 2 with isocyanate, acyl chloride or CS2 in the presence of K2CO3 or NEt3 generated pyrimido[1,6-c]quinazolin-4-ones 4, 6 or 8 in moderate to good yield.

• 出版日期2010-10-9
• 单位华中师范大学