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Literature DB >> 23808576

One-pot construction of 3,3'-bisindolylmethanes through Bartoli indole synthesis.

Takumi Abe¹, Shuuhei Nakamura, Reiko Yanada, Tominari Choshi, Satoshi Hibino, Minoru Ishikura.

Abstract

A one-pot approach to 3,3'-bisindolylmethane derivatives from nitrobenzene derivatives through the Bartoli indole synthesis was developed, in which the acid used to quench the reaction markedly affected its outcome. Quenching the reaction with concd HCl produced 3,3'-bisindolylmethane in contrast to the formation of 7-substituted indole by quenching with NH4Cl.

Entities: Chemical

Mesh：

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Year: 2013 PMID： 23808576 DOI： 10.1021/ol401486s

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

9 in total

1. Catalyst-free visible-light-induced condensation to synthesize bis(indolyl)methanes and biological activity evaluation of them as potent human carboxylesterase 2 inhibitors.

Authors: Yi-Shu Zhao; Hong-Li Ruan; Xiu-Yang Wang; Chen Chen; Pei-Fang Song; Cheng-Wei Lü; Li-Wei Zou
Journal: RSC Adv Date: 2019-12-03 Impact factor: 4.036

2. Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane.

Authors: J Pablo García Merinos; Heraclio López Ruíz; Yliana López; Susana Rojas Lima
Journal: Lett Org Chem Date: 2015-06 Impact factor: 0.867

3. Porous metal oxides derived from Cu-Al layered double hydroxide as an efficient heterogeneous catalyst for the Friedel-Crafts alkylation of indoles with benzaldehydes under microwave irradiation.

Authors: Thanh-Truc Hoang Nguyen; Xuan-Trang Thi Nguyen; Chinh Quoc Nguyen; Phuong Hoang Tran
Journal: Heliyon Date: 2018-11-24

4. Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy.

Authors: Tomoki Itoh; Yuusuke Chiba; Shunsuke Kawaguchi; Yuki Koitaya; Yuuma Yoneta; Koji Yamada; Takumi Abe
Journal: RSC Adv Date: 2019-04-03 Impact factor: 4.036

5. Bis-indolylation of aldehydes and ketones using silica-supported FeCl₃: molecular docking studies of bisindoles by targeting SARS-CoV-2 main protease binding sites.

Authors: Barnali Deb; Sudhan Debnath; Ankita Chakraborty; Swapan Majumdar
Journal: RSC Adv Date: 2021-09-16 Impact factor: 4.036

One-pot construction of 3,3'-bisindolylmethanes through Bartoli indole synthesis.

1. Catalyst-free visible-light-induced condensation to synthesize bis(indolyl)methanes and biological activity evaluation of them as potent human carboxylesterase 2 inhibitors.

2. Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane.

3. Porous metal oxides derived from Cu-Al layered double hydroxide as an efficient heterogeneous catalyst for the Friedel-Crafts alkylation of indoles with benzaldehydes under microwave irradiation.

4. Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy.

5. Bis-indolylation of aldehydes and ketones using silica-supported FeCl₃: molecular docking studies of bisindoles by targeting SARS-CoV-2 main protease binding sites.

Review 6. Chemistry of trisindolines: natural occurrence, synthesis and bioactivity.

Review 7. Technologies for Solubility, Dissolution and Permeation Enhancement of Natural Compounds.

8. A new approach for the synthesis of bisindoles through AgOTf as catalyst.

9. Synthesis, antioxidant and cytoprotective activity evaluation of C-3 substituted indole derivatives.