Premium
Synthesis of Compounds Related to Steroids. Reactions of β‐Methyltricarballylic Acid Anhydride with Substituted Naphthalenes
Author(s) -
Harnik M.,
Jensen E. V.
Publication year - 1965
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.196500003
Subject(s) - chemistry , succinic anhydride , reagent , organic chemistry , condensation , acid anhydride , naphthalene , friedel–crafts reaction , medicinal chemistry , catalysis , physics , epoxy , thermodynamics
β‐Methyltricarballylic acid anhydride (I) reacted with the Grignard reagent from 1‐iodo‐6‐methoxynaphthalene to give the keto acid (III) which was converted into the tricyclic intermediate (VIb). Friedel‐Crafts condensation of the anhydride (1) with 2‐methoxynaphthalene led to the isolation of the acids (XII) and (IXc). As in the case of 7‐methoxy‐1‐acetnaphthalide, condensation of 7‐bromo‐1‐acetnaphthalide with succinic anhydride gave only the 3‐substituted product (XVIIa). Condensation of 1‐acetnaphthalide with succinic anhydride lead to acidic products in which the naphthalene nucleus is substituted mostly in the β‐position.