THE REACTIVITY OF NAPHTHOPYRAN-2-ONE DERIVATIVES TOWARD NUCLEOPHILIC AND ELECTROPHILIC REAGENTS

Abstract

Abstract Claisen condensation of 4-methyl(2H)naphtho[1,2-6]pyran-2-one (1) with esters, gave 4-acetonyl (2H) naphtha[1.2-bIpyran-2-one derivatives (2a-d), while compound (1) condensed with hydrazines and primary amines and gave N-(substituted)-4-methyl benzo [h] quinoline-2 (1H) one derivatives (3s-d). Compound (1) reacted with Grignard reagents and gave alkyl (or aryl) 2-methylethyl l-hydroxynaphthyl ketones (4.-d). while (1) reacted with P,S, and gave 4-methyl (2H) naphtho[1.2-blpyran-2-thione (5) and 4-methyl(2H)naphtho[1,2-6]thiopyran-2-one (6). Compound (5) reacted with Grignard reagents and gave (4.-e) too. Compound (6) reacted with Grignard reagents and gave (7). Both compounds (5 and 6) reacted with primary amines and gave compound (3). The addition of (1) to acrylonitrile gave 2-Oxo(ZH)naphtho[1.2-61pryan-4-butyramide (8). while bromination of (1) gave 3,6-dibromo-4-methyl(2H)naphtho[1,2-b]pyran-2-one (9)