High-Yield Method for the Preparation of 1,3,4,5-Tetrahydro-7-methoxy-2H-1-benzazepin-2-one with Excellent Regio- and Stereoselectivity

Abstract

We have surveyed the effects of different acid catalysts, reaction times, and temperatures on the yield, regioselectivity, and stereoselectivity and calculated the ketoxime isomerization and activation energy of the title compound. A facile synthetic procedure with good yields and good regio- and stereoselectivity for Beckmann rearrangement of oxime sulfonate with ZnCl₂ in the presence of solvent is developed.

GRAPHICAL ABSTRACT

Keywords:

• Beckmann rearrangement
• ketoxime
• regio- and stereoselectivity

ACKNOWLEDGMENT

This work was supported by the National Natural Science Foundation of China (No. 30860340 and No. 21162031).

Notes

^a Based on the spot size ratio of the products on a TLC plate.

^b GC yield.

^c Isolated yield.

^a Based on the spot size ratio of the products on a TLC plate.

^a Based on the spot size ratio of the products on a TLC plate.

^b GC yield.

^c Isolated yield.

^d Not tested.