Issue 0, 1979
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

Vijay K. Tripathi,   Pudukkottai S. Venkataramani  and  Goverdhan Mehta  

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).

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Article information

DOI
https://doi.org/10.1039/P19790000036
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 36-41

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

V. K. Tripathi, P. S. Venkataramani and G. Mehta, J. Chem. Soc., Perkin Trans. 1, 1979, 36 DOI: 10.1039/P19790000036

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