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

A technology of diaryl dihydrocoumarins and compounds, applied in organic chemistry methods, organic chemistry, etc., can solve the problems of rare reports and limitations of trans products

Active Publication Date: 2021-07-13
INST OF NEW MATERIALS & IND TECH WENZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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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.Bio

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

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Embodiment Construction

[0025] Below in conjunction with specific embodiment, the present invention is described in further detail. In the following, unless otherwise specified, all reagents used were purchased from commercial sources without further purification. The progress of the reaction was monitored by TLC. The silica gel used is 300-400 mesh silica gel. Diastereoselectivity and related configurations based on 1 H NMR and obtained by the method of literature Org. Lett., 2018, 20, 4769.

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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...

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Application Information

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IPC IPC(8): C07D311/20
CPCC07D311/20C07B2200/09
Inventor 李龙罗文丰钱鹏程
Owner INST OF NEW MATERIALS & IND TECH WENZHOU UNIV
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