Preparation method of trans-3, 4-diaryl dihydrocoumarin compound

Abstract

The invention discloses an effective regioselectivity and diastereoselectivity method. A trans-3, 4-diaryl dihydrocoumarin compound is prepared through [4 + 2] cyclization reaction of alkyne amine and o-hydroxybenzyl alcohol under the condition of non-metal catalysis. Alkyne amine is used as a 2-pi partner and reacts with o-hydroxybenzyl alcohol through the positioning effect of sulfonamide, and various trans-3, 4-diaryl dihydrocoumarin compounds are prepared with good yield and high regioselectivity and diastereoselectivity. The non-metal catalytic reaction method has a wide substrate application range and good functional group tolerance, and can be used for efficiently producing in a gram scale.

Description

technical field [0001] This application belongs to the technical field of basic organic synthesis methodology, and specifically relates to the preparation of trans-3,4-diaryl by the [4+2] cyclization reaction of alkyne amines and o-hydroxybenzyl alcohol under metal-free catalytic conditions A new approach to dihydrocoumarins. Background technique [0002] Heterocyclic structures containing coumarin and its derivatives widely exist in natural products and pharmaceutically active molecular structures, especially trans-3,4-diaryldihydrocoumarin derivatives due to their anti-breast cancer and Good biological activity in anti-osteogen drugs has been widely concerned (see formula 1 below). However, there are still few methods that can be directly used to synthesize such valuable oxygen-containing heterocyclic compounds. Therefore, there is an urgent need to develop novel synthetic strategies to construct trans-3,4-diaryldihydrocoumarins in a flexible, efficient and good diastere...

AI Technical Summary

Problems solved by technology

However, despite these important synthetic pathways disclosed by the prior art, most of the intermolecular [4+2] cyclization reactions have so far been limited to the construction of cis-3,4-diaryldihydrocoumarin backbones structure, while trans products are rarely reported (Org.Biomol.Chem., 2018, 16, 9382; Adv.Synth.Catal., 2018, 360, 1128;)

In addition, alkynes, as synthons with two carbon atoms, react with o-quinone methides (o-QMs) for the preparation of 3,4-diaryldihydrocoumarins The skeleton structure of the protein has not been seen in prior art reports

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