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Cyclization of ethyl (E)/(Z)-[2-(1-cyclohexen-1-yl)cyclohexylidene]cyanoacetate to 10-amino-1,2,3,4,5,6,7,8-octahydrophenanthrene-9-carboxylic acid — a route to 1,2,3,4,5,6,7,8-octahydrophenanthrene derivatives

✍ Scribed by Wilamowski, Jaroslaw ;Krasodomski, Wojciech ;Nowak, Barbara ;Sepioł, Janusz J.

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
389 KB
Volume
1995
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Cyclization of ethyl (E)/(Z)‐[2‐(1‐cyclohexen‐1‐yl)cyclohexylidene]cyanoacetate (2) in cold concentrated sulfuric acid affords 10‐amino‐1,2,3,4,5,6,7,8‐octahydrophenanthrene‐9‐carboxylic acid (4) and 3,5,6,7,8,8a‐hexahydro‐3‐oxospiro‐[1__H__‐2‐benzopyran‐1,1′‐cyclohexane]‐4‐carbonitrile (5). The o‐amino acid 4 is employed in the synthesis of several 1,2,3,4,5,6,7,8‐octahydrophenanthrene derivatives: the carboxylic acid 6, o‐hydroxy carboxylic acid 7, and the amine 8. The lactone 5 undergoes decarboxylation on heating yielding a mixture of unsaturated nitriles 9 and 10 which are cyclized to the amine 8.

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