Original scientific paper

Synthesis and Properties of the Stereoisomeric Diethyl 2-Aminocyclohexane-1,6-dicarboxylates

V. Škarić ; Laboratory of Stereochemistry and Natural Products, Institute »Ruder Boskovic«, 41001 Zagreb, Croatia, Yugoslavia
B. Djuras ; Laboratory of Stereochemistry and Natural Products, Institute »Ruder Boskovic«, 41001 Zagreb, Croatia, Yugoslavia
V. Turjak-Zebić ; Laboratory of Stereochemistry and Natural Products, Institute »Ruder Boskovic«, 41001 Zagreb, Croatia, Yugoslavia

Abstract

The stereoisomeric driethyl 2-aminocyclohexane-1,6-dicarboxylates
(Ia-d) have be€!1 synthesised from diethyl 2-hydroxy:iminocyclohexane-
1,6-dicarboxylate (III) a.nd deaminated to corresponding
2-hydroxy derivatives (IIa-d) along w.ith cyclohexenes. The amiir).es
I and the alcohols II were characterized as their N- and 0-benzoyl
dedvatives, respectively. While the oxime III undergoes ~ntramolecular
cyc11sation to give ethyl 3,3a,4,5,6,7-hexahydro-3-oxo-(
2,1)-benzisoxazole-4-carboxylate (IV), spontaneous cyclisation of
c-2-arninocyclohexa.ne-r-1,c-6-dicarboxylate (Id) afforded ethyl 7-
-oxo-6-azabicyclo[3.2.1] octane-8-carboxylate (VI).

Keywords

Hrčak ID:

196465

URI

https://hrcak.srce.hr/196465

Publication date:

23.9.1976.

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