Original scientific paper

Synthesis of Isomeric Hexahydro- and Perhydroisoindol-1-ones

V. Škarić ; Laboratory of Stereochemistry and Natural Products, »Ruder Bo!ikovic« Institute, 41001 Zagreb, Croatia, Yugoslavia
D. Frgačić ; Laboratory of Stereochemistry and Natural Products, »Ruder Bo!ikovic« Institute, 41001 Zagreb, Croatia, Yugoslavia
V. Turjak-Zebić ; Laboratory of Stereochemistry and Natural Products, »Ruder Bo!ikovic« Institute, 41001 Zagreb, Croatia, Yugoslavia

Abstract

Catalytic hydrogenation of triethyl 2-cyanocyclohex-1-(XIV)
and -2(XV)-ene-1,5,5-tricarboxylates yielded the corresponding 2-
-cyanocyclohexane (XVII) and diethyl perhydroisoindol-1-one-6,6-
-dicarboxylate (V), the latter being formed through spontaneous
intramolecular cyclisation of triethyl 2-aminomethylcyclohexane-
1,5,5-tricarboxylate (XXI). Regiospecific reductions and isomerisations
of cyanocyclohexenes (XIV) and (XV), and their conversion
into corresponding hexahydroisoindol-1-ones (IV) and (III) were
shown to depend on the hydrogenating conditions and catalysts.

Keywords

Hrčak ID:

195985

URI

https://hrcak.srce.hr/195985

Publication date:

26.6.1978.

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