Efficient synthesis of naphtho[1,2-e][1,3]oxazine derivatives via a chemoselective reaction with the aid of low-valent titanium reagent.
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.
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
Daqing
D
Shi
Shaofeng
S
Rong
Guolan
G
Dou
Manman
M
Wang
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis*; D010078:Oxazines / Q000138:chemical synthesis*; D013379:Substrate Specificity; D013997:Time Factors; D014025:Titanium / Q000737:chemistry*
D009284:Naphthols; D010078:Oxazines; D014025:Titanium