Richard V. Connors, Elisa Tran, T. Durst
Feb 1, 1996
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0
Influential Citations
12
Citations
Journal
Canadian Journal of Chemistry
Abstract
Irradiation of 2-methylbenzoyl cyanide (3a) in acetonitrile solution results in the formation of its dimer, which upon loss of HCN gives rise to the cycloadduct 7a. The dimerization also proceeds efficiently with derivatives of 3a giving adducts 7b and 7c. When 2-methylaroyl cyanides are photolyzed in the presence of a more reactive acyl cyanide the mixed adducts 8a–e are obtained in excellent yields. The cycloadducts 7a–c and 8a–e react with carbon and nitrogen nucleophiles by a tandem addition–cyclization sequence furnishing substituted naphthols (10a and 10b) and isoquinolones (11a–d), respectively. Isocoumarins 12a and 12b were prepared from the adducts 8a and 8e by treatment with potassium tert-butoxide in THF. Key words: naphthols, isoquinolones, isocoumarins, synthesis of; acyl cyanides; hetero Diels–Alder.