A new convenient synthetic route towards 2-(hetero)aryl-substituted thieno[3,2-b]indoles using Fischer indolization

2018 ◽  
Vol 16 (26) ◽  
pp. 4821-4832 ◽  
Author(s):  
Roman A. Irgashev ◽  
Alexander S. Steparuk ◽  
Gennady L. Rusinov
Keyword(s):  
Synthetic Route ◽  
Fischer Indole Synthesis ◽  
Fischer Indolization ◽  
Indole Synthesis

A series of 2-(hetero)aryl-substituted thieno[3,2-b]indoles has been successfully prepared using an effective three-step strategy based on Fischer indole synthesis.

Fischer Indole Synthesis with Selected 2,3-Dideoxy-D-glycero-aldopentose Derivatives. Conversion of D-Xylose to (2S)-3-(Indol-3-yl)propane-1,2-diol

1996 ◽  
Vol 61 (2) ◽  
pp. 298-304 ◽  
Author(s):  
Stevan Lajšic ◽  
Gordana Cetkovic ◽  
Mirjana Popsavin ◽  
Velimir Popsavin ◽  
Dušan Miljković
Keyword(s):  
Acid Hydrolysis ◽  
Raney Nickel ◽  
Good Yield ◽  
Dimethyl Acetal ◽  
Fischer Indole Synthesis ◽  
Fischer Indolization ◽  
Efficient Route ◽  
Indole Synthesis ◽  
Hydrolysis Of

Two independent routes towards (2S)-3-(indol-3-yl)propane-1,2-diol (11) were achieved starting from 3,5-di-O-acetyl-1,2-O-cyclohexylidene-α-D-xylofuranose (1). Ethanethiolysis of 1 afforded acyclic diethyl dithioacetal 2 which was further O-deacetylated to give 3. Selective benzoylation of 3 gave 5-O-benzoyl derivative 4. Treatment of 4 with N-bromosuccinimide in methanol gave methyl furanoside 5 which was further desulfurized over Raney nickel to afford 6. An acid hydrolysis of 6 gave hemiacetal 7 which upon treatment with phenylhydrazine, according to standard Fischer indolization procedure, yielded a mixture of chiral indoles 10. O-Debenzoylation of 10 gave the crystalline diol 11. A more efficient route towards the chiral indole 11 included the initial dethioacetalation of 2 into dimethyl acetal 8 which was further desulfurized over Raney nickel to give the corresponding 2,3-dideoxy derivative 9. Direct Fischer indolization of 9 with phenylhydrazine, followed by O-deacetylation of intermediate 12, afforded the expected indole 11 in good yield.

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

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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