Tandem reactions of 1,3-diacid chlorides with 2-methylimidazoline and 2-methyl-1,4,5,6-tetrahydropyrimidine: one-pot synthesis of 1,8-naphthyridinetetraones

Guozhong Ye; Aihua Zhou; William P Henry; Yingquan Song; Sabornie Chatterjee; Debbie J Beard; Charles U Pittman Jr

doi:10.1021/jo8009177

Tandem reactions of 1,3-diacid chlorides with 2-methylimidazoline and 2-methyl-1,4,5,6-tetrahydropyrimidine: one-pot synthesis of 1,8-naphthyridinetetraones

J Org Chem. 2008 Jul 4;73(13):5170-2. doi: 10.1021/jo8009177. Epub 2008 Jun 11.

Authors

Guozhong Ye¹, Aihua Zhou, William P Henry, Yingquan Song, Sabornie Chatterjee, Debbie J Beard, Charles U Pittman Jr

Affiliation

¹ Department of Chemistry, Mississippi State University, Mississippi State, Mississippi 39762, USA.

PMID: 18543994
DOI: 10.1021/jo8009177

Abstract

The reactions of 2-methylimidazoline and 2-methyl-1,4,5,6-tetrahydropyrimidine with 1,3-diacid chlorides, in the presence of Et3N in refluxing MeCN give highly functionalized potentially bioactive 1,8-naphthyridinetetraones. 2-Methylimidazoline and 2-methyl-1,4,5,6-tetrahydropyrimidine can be viewed as tridentate nucleophiles which give four consecutive tandem nucleophilic attacks on electrophiles.