Divergent Pathways for Reactions of 3-Formylchromone with Cyclic Secondary Amines in Alcoholic Media

Author:

Korzhenko Kirill S.,Osipov Dmitry V.ORCID,Osyanin Vitaly A.1,Klimochkin Yuri N.

Affiliation:

1. Department of Organic Chemistry, Samara State Technical University

Abstract

Reaction of 3-formylchromone with cyclic secondary amines in methanol results in (E)-2-methoxy-3-(R2N-methylene)chroman-4-ones, while use of ethanol leads to (E)-2-morpholino-3-(morpholino­methylene)chroman-4-one or enaminoketones as dihydropyran ring-opening products. The solubility of the formed products in alcoholic media is postulated to be a key factor that determines the reaction pathway.

Funder

Russian Foundation for Basic Research

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Materials Science (miscellaneous),Biomaterials,Catalysis

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