Original scientific paper

4,5,6, 7-Tetrahydroindazol-3-one Carboxylic Acids. III. Reductive Cleavage Related to Conformational Analysis of 2-Carboxamide-4,4-dicm.·bethoxy-cyclohexylamine

Đ. Škarić ; Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia
V. Škarić ; Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia
V. Turjak-Zebić ; Institute »Ruder Boskovic«, Zagreb, Croatia, Yugoslavia

Abstract

2-Carboxamide-4,4-dicarbethoxy-cyclohexylamine (II) with
axial amino group satisfied the :necessary geometrical requirement
of coplanarity in an elimination reaction with nitrous acid
yielding mostly cyclohexene derivatives.
The conformational analysis of cyclohexylamine II provided
the evidence for the stereoselectivity of the Raney nickel-catalyst
as well as for stereospeaific reductive openirng of diethyl 4,5,6,
7 -tetrahydroindazol-3-one-5,5-dicarboxylate (I).
The reductive cleavage of I using Raney nickel-catalyst in
ethanol yielded the Schiff base VI besides 2-carboxamide-4,4-
-dicarbethoxy-N-ethylcyclohexylamine (VII). The conformations
of VI and VII were interrelated to that of cyclohexylamine II.
The properties and synthesis of 4,5,6,7-tetrahydroindazol-
3-one-5-carboxylic acid (IX) and its ethylester VIII are described.

Keywords

Hrčak ID:

208325

URI

https://hrcak.srce.hr/208325

Publication date:

28.2.1964.

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