Synthesis of new 3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-diones via the tandem intramolecular Pinner/Dimroth rearrangement

Heterocyclic communications

article

Nasrin Karimi¹  Abolghasem Davoodnia¹  Mehdi Pordel¹ 

[1] Department of Chemistry, Mashhad Branch, Islamic Azad University

关键词: carboxylic acids;    chromeno[2;    3-d]pyrimidines;    Pinner/Dimroth rearrangement;    POCl3;   

DOI  :  10.1515/hc-2017-0228

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

The reaction of 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4 H -chromene-3-carbonitriles with excess aliphatic carboxylic acids in the presence of phosphoryl chloride (POCl 3 ) afforded new 2-alkyl-5-aryl-8,8-dimethyl-8,9-dihydro-3 H -chromeno[2,3- d ]pyrimidine-4,6(5 H , 7H )-diones in high yields. The suggested mechanism involves a tandem intramolecular Pinner/Dimroth rearrangement. The synthesized compounds were characterized by infrared (IR), proton nuclear magnetic resonance ( 1 H NMR), carbon-13 nuclear magnetic resonance ( 13 C NMR) and elemental analysis.

【 授权许可】

CC BY|CC BY-NC-ND