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.
Shi
Daqing
D
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
Rong
Shaofeng
S
Dou
Guolan
G
Wang
Manman
M
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