Synthesis of Compounds Related to Steroids. Reactions of β‐Methyltricarballylic Acid Anhydride with Substituted Naphthalenes
1965; Wiley; Volume: 3; Issue: 1 Linguagem: Inglês
10.1002/ijch.196500003
ISSN1869-5868
Autores Tópico(s)Synthesis of heterocyclic compounds
ResumoAbstract 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.
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