1,1-Disubstituted-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indolecarboxylic acid esters and ketones. The base catalyzed transformation of 1-(2′,3′,4′,9′-tetrahydrospiro[cyclohexane-1,1′-[1H]pyrido[3,4-b]indol]-2-yl)alkanones into 2-(4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)-1 -alkylcyclohexanols

Author:

Bobowski George,Shavel John

Publisher

Wiley

Subject

Organic Chemistry

Reference7 articles.

1. Synthesis of 1-substituted-2,3,4,9-tetrahydro-(2-oxopropyl)-1H-pyrido [3,4-b] indoles and their base-catalyzed rearrangements toN- [2-[2-(1-alkyl-3-oxobutenyl)-1H-indol-3-yl] ethyl]acetamides

2. The ratio of 10 to 11 as determined by tlc and 1H nmr of the crude mixture was only approximate. However, the amount of isolated minor isomer 11 by direct crystallization was much less (cf. Table III) since a considerable amount of it invariably remained in the mother liquor.

3. 2′,3′,4′,9′-Tetrahydrospiro[cyclohexane-1,1′-(1h)pyrido[3,4-b]indol]-2-ones and their transformations into 2,3,4,4a,5,6,9,14-octahydro-4a-hydroxy-1h,8h-pyrido[3,4-b:2,1-i']diindole-5-carbonitriles and 5-substituted 2,3,4,4a,9,14-hexahydro-4a-hydroxy-1H,8H-indolo[2′,3′:3,4]-pyrido[1,2-c]benzimidazol-6-(5H)ones

4. As shown in Table IV, yields of isolated pure products 12 are considerably lower since some decomposition unavoidably occurred under reaction conditions.

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