One-Pot Synthesis of Hexahydroquinolines via Hantzsch Four-Component Reaction Catalyzed by a Cheap Amino Alcohol

Abstract

An economic, efficient access to hexahydroquinolines was found. In the presence of threo-(1S,2S)-2-amino-1-(4′-nitrophenyl)-1,3-propanediol, a waste product formed in the production of chloromycetin, a one-pot, four-component Hantzsch reaction of dimedone, aldehydes, ethyl acetoacetate, and ammonium acetate at room temperature furnished hexahydroquinoline derivatives in excellent yield. A possible catalytic mechanism was also suggested.

Keywords:

• Amino alcohol
• Hantzsch reaction
• hexahydroquinolines
• one-pot synthesis

ACKNOWLEDGMENT

We thank the National Natural Science Foundation of China (Nos. 20672083 and 20872115) for financial support.

Notes

^a Refers to isolated yield.

^a Refers to isolated yield.

^a Refers to isolated yield.