Addition of nitrogen-, oxygen-, and sulphur-containing nucleophiles to aryl ethynyl ketones

Abstract

Addition of some nitrogen-, oxygen-, and sulphur-containing nucleophiles to the aryl ethynyl ketones (1)–(4) has been examined. Addition of o-phenylenediamine and o-aminophenol yielded the corresponding cis-β-aminovinyl ketones (5)–(7) and (10)–(12). Addition of secondary amines (morpholine and piperidine) yielded the trans-β-aminovinyl ketones (13)–(20). Catechol reacted with aryl ethynyl ketones to furnish 1,3-benzodioxole derivatives (21)–(23), salicylic acid and 2-hydroxy-3-naphthoic acid to give the oxalactones (24)–(30). However, 2-hydroxy-1-naphthoic acid yielded a mixture of the oxalactones (31)–(33) and 3-naphthoxy-1-arylprop-2-enones (35) and (36). Similarly thiosalicylic acid gave the corresponding thialactones (40) and (41) as addition products. Salicylaldehyde reacted with ethynyl phenyl ketone to give 3-benzoylchrom-3-en-2-ol (38).