New efficient synthesis of pyrimido[1,6-c]quinazolin-4-ones by a Biginelli 3CC/Staudinger/aza-Wittig sequence |
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Authors: | Wen-Jing Li |
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Institution: | Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079, PR China |
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Abstract: | 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 pyrimido1,6-c]quinazolin-4-ones 4, 6 or 8 in moderate to good yield. |
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Keywords: | GPCTVKCTVBHIQG-UHFFFAOYSA-N JYXNJQSUDCKJFA-UHFFFAOYSA-N PCUOVTMIEFEYPW-UHFFFAOYSA-N XYUKBHBHTUIJLL-UHFFFAOYSA-N WBUQRRDCFXJZFU-UHFFFAOYSA-N WOXVSMZPSPUADH-UHFFFAOYSA-N |
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