Synthesis of 1-[2-(1,3-benzoxazol-2-yl)-2-oxoethylidene]-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives

Heterocyclization of caprolactam hydrazidine by the action of 2,3-dioxopyrrolo[2,1-a]isoquinolines

“…In previous work [1,2], we showed that the reaction of 2,3-dioxopyrrolo[2,1-a]isoquinolines with several dinucleophiles might proceed with opening of the lactam bond and concurrent heterocyclization. The reactions of these compounds with cyclic hydrazidines have not yet been reported.…”

Reaction of 2,3-dioxopyrrolo[2,1-a]iso-quinolines with binucleophiles

“…These examples show that the reactions of these compounds with binucleophiles may proceed through various pathways, namely, ordinary acylation of the amino group [1], annelation of the heterocycle [2, 4], and heterocyclization with benzoxazole formation [5]. In the present work, we studied the dependence of the structure of the products on the structure of both the binucleophile and the dicarbonyl reagent.…”

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Keywords: o-aminobenzyl alcohol, 2-amino-4-methylphenol, o-aminothiophenol, N-benzylamide, benzyl ester, anthranilic acid hydrazide, caprolactam hydrazidine, o-hydroxybenzylamine, diacyl hydrazide, 5,5-dialkyl-2,3-dioxopyrrolo[2,1-a]isoquinolines, benzoxazole, benzothiazole, and 1,2,4-triazole derivatives.We have already studied the reactions of 2,3-dioxopyrrolo[2,1-a]isoquinolines with several binucleophiles such as aliphatic diamines [1], o-phenylenediamine [2][3][4], and o-aminophenol [5]. These examples show that the reactions of these compounds with binucleophiles may proceed through various pathways, namely, ordinary acylation of the amino group [1], annelation of the heterocycle [2, 4], and heterocyclization with benzoxazole formation [5].

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“…We have already studied the reactions of 2,3-dioxopyrrolo[2,1-a]isoquinolines with several binucleophiles such as aliphatic diamines [1], o-phenylenediamine [2][3][4], and o-aminophenol [5]. These examples show that the reactions of these compounds with binucleophiles may proceed through various pathways, namely, ordinary acylation of the amino group [1], annelation of the heterocycle [2, 4], and heterocyclization with benzoxazole formation [5].…”