SIX-MEMBERED RING FORMATION DURING FISCHER INDOLE SYNTHESIS

1958 ◽  
Vol 80 (20) ◽  
pp. 5574-5575 ◽  
Author(s):  
H. Rapoport ◽  
J. R. Tretter
Keyword(s):  
Membered Ring ◽  
Ring Formation ◽  
Fischer Indole Synthesis ◽  
Indole Synthesis

scholarly journals Convenient Synthesis of 6,7,12,13-Tetrahydro-5H-Cyclohepta[2,1-b:3,4-b’]diindole Derivatives Mediated by Hypervalent Iodine (III) Reagent

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 960 ◽  
Author(s):  
Lei Peng ◽  
Xiaofei Zhang ◽  
Chunhao Yang
Keyword(s):  
Oxidative Coupling ◽  
Biological Activities ◽  
Condensation Reaction ◽  
Large Family ◽  
Membered Ring ◽  
Hypervalent Iodine ◽  
Fischer Indole Synthesis ◽  
Convenient Synthesis ◽  
First Time ◽  
Indole Synthesis

Bisindolyl alkaloids represent a large family of natural and synthetic products that display various biological activities. Among the bisindole compounds, 6,7,12,13-tetrahydro-5H-cyclohepta[2,1-b:3,4-b’]diindoles have received little attention. Only two methods have been developed for the construction of the 6,7,12,13-tetrahydro-5H-cyclohepta[2,1-b:3,4-b’]diindole scaffold thus far, including the classical Fischer indole synthesis conducted by reacting indole-fused cycloheptanone and hydrazines, and the condensation reaction to build the seven-membered ring. Here, we report for the first time a new route to synthesize 6,7,12,13-tetrahydro-5H-cyclohepta[2,1-b:3,4-b’]diindoles through intramolecular oxidative coupling of 1,3-di(1H-indol-3-yl)propanes in the presence of PIFA, DDQ and TMSCl with moderate to excellent yields.

Modular Counter-Fischer–Indole Synthesis through Radical-Enolate Coupling

2021 ◽  
Vol 23 (3) ◽  
pp. 1096-1102
Author(s):  
Hyunho Chung ◽  
Jeongyun Kim ◽  
Gisela A. González-Montiel ◽  
Paul Ha-Yeon Cheong ◽  
Hong Geun Lee
Keyword(s):  
Fischer Indole Synthesis ◽  
Indole Synthesis

Ring formation via β-keto ester dianions

1977 ◽  
Vol 55 (6) ◽  
pp. 996-1000 ◽  
Author(s):  
Phaik-Eng Sum ◽  
Larry Weiler
Keyword(s):  
Membered Ring ◽  
Ring Formation ◽  
Methyl Acetoacetate ◽  
Keto Ester ◽  
Keto Esters

The reaction of α,ω-dihalides with the dianion of methyl acetoacetate gives a mixture of mono- and bisalkylated products. The monoalkylated products can be cyclized via the monoanion to cyclic β-keto esters with a seven- or eight-membered ring. Alternatively these monoalkylated products can be cyclized via the dianion to γ-cyclopentyl- or γ-cyclohexyl-β-keto esters.

A continuous flow microwave-assisted fischer indole synthesis of 7-Ethyltryptophol

2017 ◽  
Vol 121 ◽  
pp. 144-148 ◽  
Author(s):  
Jianguo Xu ◽  
Jiangang Yu ◽  
Yi Jin ◽  
Jie Li ◽  
Zhiqun Yu ◽  
...  
Keyword(s):  
Continuous Flow ◽  
Microwave Assisted ◽  
Fischer Indole Synthesis ◽  
Indole Synthesis

scholarly journals Polyphosphate Ester as a Synthetic Agent. V. The Fischer Indole Synthesis with Polyphosphate Ester

1966 ◽  
Vol 14 (9) ◽  
pp. 934-939 ◽  
Author(s):  
Yuichi Kanaoka ◽  
Yoshio Ban ◽  
Koichi Miyashita ◽  
Kimiko Irie ◽  
Osamu Yonemitsu
Keyword(s):  
Fischer Indole Synthesis ◽  
Indole Synthesis

One-Pot Reactions Involving the Fischer Indole Synthesis and Friedel–Crafts Reactions

2018 ◽  
Vol 61 (7-8) ◽  
pp. 685-688 ◽  
Author(s):  
Hien Vuong ◽  
Samantha Duarte ◽  
Douglas A. Klumpp
Keyword(s):  
One Pot ◽  
Fischer Indole Synthesis ◽  
Indole Synthesis
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