Efficient synthesis of naphtho[1,2-e][1,3]oxazine derivatives via a chemoselective reaction with the aid of low-valent titanium reagent

Daqing Shi; Shaofeng Rong; Guolan Dou; Manman Wang

doi:10.1021/cc900073w

Efficient synthesis of naphtho[1,2-e][1,3]oxazine derivatives via a chemoselective reaction with the aid of low-valent titanium reagent

J Comb Chem. 2010 Jan-Feb;12(1):25-30. doi: 10.1021/cc900073w.

Authors

Daqing Shi¹, Shaofeng Rong, Guolan Dou, Manman Wang

Affiliation

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, PR China. dqshi@suda.edu.cn

PMID: 19863097
DOI: 10.1021/cc900073w

Abstract

A series of new naphtho[1,2-e][1,3]oxazine derivatives such as trans-1,3-diaryl-1H-naphtho[1,2-e][1,3]oxazine-2(3H)-carbonyl chloride, 1-aryl-2-benzyl-1,2- dihydronaphtho[1,2-e][1,3]oxazine-3-one, and trans-1,3-diaryl-1H-naphtho[1,2-e] [1,3]oxazine-2(3H)-carbaldehyde were selectively synthesized via a chemoselective reaction of 1,3-diaryl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines and triphosgene or triethyl orthoformate, respectively, induced by different low-valent titanium systems. This method has the advantages of short reaction time (15 min), convenient manipulation, and high chemoselectivity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Combinatorial Chemistry Techniques / methods*
Magnetic Resonance Spectroscopy
Molecular Structure
Naphthols / chemical synthesis*
Oxazines / chemical synthesis*
Substrate Specificity
Time Factors
Titanium / chemistry*

Substances

Naphthols
Oxazines
Titanium