Thermal ring expansion of 2-azidoselenochromenes: first synthetic examples of 1,3-benzoselenazepines.
The thermolysis of 2-azido-2-tert-butyl-2H-selenochromenes (2a, b), which were easily obtained by the reaction of the corresponding 1-benzoselenopyrylium salts (1) with sodium azide, resulted in a ring expansion to give the novel stable 1,3-benzoselenazepines (5a, b) with denitrogenation in good yields.
Sashida
Haruki
H
Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, Japan. h-sashida@hokuriku-u.ac.jp
Minamida
Hiroshi
H
D001552:Benzazepines / Q000138:chemical synthesis*; D001578:Benzopyrans / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D016566:Organoselenium Compounds / Q000138:chemical synthesis*; D019810:Sodium Azide / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
D001552:Benzazepines; D001578:Benzopyrans; D007202:Indicators and Reagents; D016566:Organoselenium Compounds; D019810:Sodium Azide