Mechanistic and exploratory investigations into the synthesis of 1, 3, 5-triaroylbenzenes from 1-aryl-2-propyn-1-ones and 1, 3, 5-triacetylbenzene from 4-methoxy-3- …

T Iwado, K Hasegawa, T Sato, M Okada…

Index: Iwado, Tatsuya; Hasegawa, Keiya; Sato, Toshiyuki; Okada, Masaki; Sue, Kiwamu; Iwamura, Hiizu; Hiaki, Toshihiko Journal of Organic Chemistry, 2013 , vol. 78, # 5 p. 1949 - 1954

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Citation Number: 10

Abstract

Neat 1-phenyl-and 1-(p-tolyl)-2-propyn-1-ones (1 and 1′, respectively) were heated in water without any additive at 150° C for 2 h to give 1, 3, 5-tribenzoyl-and 1, 3, 5-tri-(p-toluoyl) benzenes (2 and 2′, respectively) in 74 and 52% yields, respectively. The crossed reactions of 1 with the enolate of p-toluoylacetaldehyde (3′) and 1′ with the enolate of benzoylacetaldehyde (3) were carried out to give unsymmetrically substituted 1-toluoyl-3, ...