Michiko Enkaku

Formation of 3H-1,3-benzodiazepines from quinoline N-acylimides

Photolysis of the quinoline N-imides (3) having an electron-donating substituent in the 6- or 8-position affords the corresponding 3H-1,3-benzodiazepines (4), whereas quinolines having an electron-donating group in the other positions or an electron-withdrawing group give no diazepines.

Photolysis of thieno-, furo-, and pyrrolo-[b]pyridine N-imides: formation of 3H-1,3-diazepines

Photolysis of pyridine N-ethoxycarbonylimides condensed with thiophen, furan, and pyrrole rings on the b-side of the pyridine ring affords the corresponding novel 1H-1,2- and 3H-1,3-diazepines, respectively.

Acylations of 1H-1,2-thieno-and 1H-1,2-benzo-diazepines: ring-conversion into 1,3-diazepines

Treatment of the 1H-1,2-thienodiazepine (1) and the 1H-1,2-benzodiazepines (7) having an electron-donating substituent in the 7-position with ethyl chloroformate, acetyl chloride, or benzoyl chloride in benzene results in ring-conversion to give the corresponding 1,3-diazepines (3) and (12).

Formation of novel 1H-1,3-benzodiazepines in the photolysis of isoquinoline N-imides

Photolysis of the 1-substituted isoquinoline N-ethoxycarbonylimides (1) affords 1H-1,3-benzodiazepines (2) and the results of some reactions of this new ring are also reported.

Thermal and photochemical rearrangements of 3H-thieno-1,2-diazepines

Photolysis of the 3H-thieno-1,2-diazepines (1) affords the 3-vinylthienopyrazoles (2), whereas their thermolysis gives the thienylpyrazoles (3)via a [1,5] hydrogen shift in the diazepine ring; this mechanism has been confirmed by a deuterium-labelling experiment.