Cu(II)-catalyzed efficient construction of 1,3-naphthoxazines from 2-naphthols, amidines and N, N-dimethylethanolamine

Herein, we report a Cu(II)-catalyzed multi-component reaction for the facile synthesis of 1,3-naphthoxazines from amidines and ortho-quinone methides, which are in situ-generated from 2-naphthols and N, N-dimethylaminoethanol (DMEA). DMEA acts as a unique and efficient C1 synthon as well as reaction...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2023-10, Vol.146, p.133651, Article 133651
Main Authors: Geng, Meiqi, Kuang, Jinqiang, Miao, Maozhong, Ma, Yongmin
Format: Article
Language:English
Subjects:
1,3-Naphthoxazine
2-Naphthol
Amidine
N,N-dimethylethanolamine
o-QMs
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Herein, we report a Cu(II)-catalyzed multi-component reaction for the facile synthesis of 1,3-naphthoxazines from amidines and ortho-quinone methides, which are in situ-generated from 2-naphthols and N, N-dimethylaminoethanol (DMEA). DMEA acts as a unique and efficient C1 synthon as well as reaction solvent. A variety of 1,3-naphthoxazines with diverse functional groups were provided in moderate to excellent yields. We report a Cu(II)-catalyzed efficient method for the synthesis of 1,3-naphthoxazines via [4 + 2] cyclization of amidines and in situ-generated ortho-quinone methides (o-QMs) from readily amailable 2-naphthols and N,N-dimethylethanolamine (DMEA). DMEA acts as both reaction solvent and C1 synthon in the transformation. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2023.133651