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

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

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‐[1H‐2‐benzopyran‐1,1′‐cyclohexane]‐4‐carbonitrile (5). The o‐amino...

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Veröffentlicht in:Liebigs Annalen 1995-08, Vol.1995 (8), p.1567-1570
Hauptverfasser: Wilamowski, Jaroslaw, Krasodomski, Wojciech, Nowak, Barbara, Sepioł, Janusz J.
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Ethyl alkylidenecyanoacetates
Phenanthrenes
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container_end_page 1570
container_issue 8
container_start_page 1567
container_title Liebigs Annalen
container_volume 1995
creator Wilamowski, Jaroslaw
Krasodomski, Wojciech
Nowak, Barbara
Sepioł, Janusz J.
description 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‐[1H‐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.
doi_str_mv 10.1002/jlac.1995199508216
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subjects Ethyl alkylidenecyanoacetates
Phenanthrenes
title 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
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