ALKYL (E,Z)-2-(2-BENZOYL-2-ETHOXYCARBONYL-1-ETHENYL)AMINO-3-DIMETHYLAMINOPROPENO ATES IN THE SYNTHESIS OF FUSED PYRIMIDINONES - A FACILE ROUTE TO 3-AMINOAZINO-4H-PYRIMIDIN-4-ONE

摘要

Alkyl (E,Z)-2-(2-benzoyl-2-ethoxycarbonyl-1-ethenyl)amino-3-dimethylaminopropeno ates 1a,b react with heteroarylamines 2 to give alkyl 2-(2-benzoyl-2-ethoxycarbonyl-1-ethenyl)amino-3-heteroarylaminopropenoates 3-13. These were cyclized into fused 3-(2-benzoyl-2-ethoxycarbonyl-1-ethenyl)amino-4H-azolo-n (or azino)-pyrimidin-4-ones 14-18. 2-Benzoyl-2-ethoxycarbonyl-1-ethenyl group can be easily removed from 3-(2-benzoyl-2-ethoxycarbonyl-1-ethenyl)amino-8-methyl-4H-pyridol[1,2-a]py rimidin-4-one (14) to give 3-amino-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (19). The structure of 1a was confirmed by X-ray analysis. [References: 22]