SYNTHESIS AND REACTIVITY OF ENAMINONE OF NAPHTHO[B]1,4-OXAZINE: ONE POT SYNTHESIS OF NOVEL ISOLATED AND HETEROCYCLE-FUSED DERIVATIVES WITH ANTIMICROBIAL AND ANTIFUNGAL ACTIVITIES

2015 Islam H. El Azab*, **, # and Khaled M. Khaled**, ***

#Phone: +2097480446; fax: +2097480450; e-mail: ihelmy2003@yahoo.com; i.helmy@tu.edu.sa

*On leave from Chemistry Department, Faculty of Science, Aswan University, Aswan 81528, Egypt;
**Chemistry Department, Faculty of Science, Taif University, Al-Haweiah, P.O. box 888, Zip code 21974, Taif, Saudi Arabia;
***Chemistry Department, Faculty of Education, Ain Shams University, Roxy, Cairo, Egypt

Received December 8, 2014; in final form January 23, 2015

The synthesis of the multifunctional, hitherto unreported 3-(3-(dimethylamino)acryloyl)-2H-naphtho[1,2-b][1,4]oxazin-2-one was described and its utility as a versatile building block was demonstrated for the synthesis of some new pyrimidines, pyrazoles, isoxazoles, pyrazolo[a]pyrimidines, triazolo[a]pyrimidines, pyrido[d]pyrimidines, pyrido[d]pyrimidines, piperidines, pyrido[a]benzimidazoles, 2H-pyran-3-carboxamides, benzofurans, naphtho[b]furans and pyrazolo[c][1,2,4]triazines of potential biological activities. The synthesized compounds were characterized by IR, 1H NMR, 13C NHR and mass spectral data. Some of the compounds were evaluated for antimicrobial activities.

Keywords: 2-nitrosonaphthalen-1-ol, naphtho[b][1,4]oxazin-2-one, ethyl acetoacetate, dimethylformamide-dimethylacetal, enaminone.