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The dipolar route to naphtho[2,1‐ c ]isoxazoles from the baylis‐hillman adducts of 2‐alkynylbenzaldehydes
Author(s) -
Ji SangHoon,
Hong Wan Pyo,
Ko Seung Ho,
Lee KeeJung
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430344
Subject(s) - chemistry , adduct , nitrile , intramolecular force , medicinal chemistry , nucleophile , cycloaddition , 1,3 dipolar cycloaddition , ion , nucleophilic substitution , stereochemistry , organic chemistry , catalysis
A new synthesis of 4‐carbomethoxynaphtho[2,1‐ c ]isoxazoles 4a‐d from methyl 3‐(alkynylphenyl)‐2‐nitromethyl‐2‐propenoates 2a‐d by the intramolecular nitrile oxide cycloaddition is described. The latter are readily obtained from 2‐alkynylbenzaldehydes through the Baylis‐Hillman adduct acetates 1a‐d followed by nucleophilic substitution of nitrite anion.