Molecular-iodine catalyzed selective construction of cyclopenta[b]indoles from indoles and acetone: a green gateway to indole-fused cycles

Literature Information

Publication Date 2023-10-31
DOI 10.1039/D3OB01561K
Impact Factor 3.876
Authors

Bipul Sarma, Utpal Bora


View Original

Abstract

Molecular-iodine catalyzed access to an important class of bio-relevant indole derivatives, cyclopenta[b]indoles, has been achieved via a cascade addition/intramolecular cyclization reaction of indoles and acetone. Explorations of diverse substitution patterns revealed an essential substrate-control in the reaction. The high-density electronic core of indole is pivotal in favouring the formation of indolyl-cyclopenta[b]indole derivatives; in contrast, the electron deficiency of the core hindered the cyclization process, directing the formation of bis(indolyl)propanes. Investigations on the mechanistic pathway revealed that bis(indolyl)alkanes were the intermediates for the addition–cyclization process. This simple experimental method provides sustainable synthetic access to cyclopentannulated indoles.

Related Literature

Total synthesis, structural revision and biological evaluation of γ-elemene-type sesquiterpenes

Changchun Yuan, Shangyong Zhong, Xingyi Li, Yanhong Wang, Miao-Miao Xun, Yunli Bai, Kongkai Zhu

2018-10-03 Paper

DOI: 10.1039/C8OB02005A

Differential substituent effects of β-halogens in water-soluble porphyrins

Justin C. Biffinger, Haoran Sun, Andrew P. Nelson, Stephen G. DiMagno

2003-01-24 Paper

DOI: 10.1039/B209345F

Characterization of binary solvent mixtures: the water–acetonitrile mixture

Francisco García-Blanco

2003-01-06 Paper

DOI: 10.1039/B210405A

Syntheses and anti-cancer activity of CO-releasing molecules with targeting galactose receptors

Jili Li, Jinlong Zhang, Qiuping Zhang, Zhongjie Bai, Quanyi Zhao, Dian He, Zhen Wang, Yonglin Chen, Bin Liu

2018-10-09 Paper

DOI: 10.1039/C8OB01921E

Synthesis of a tweezer-like bis(arylthiaalkoxy)calix[4]arene as a cation sensor for ion-selective electrodes: an investigation of the influence of neighboring halogen atoms on cation selectivity‡

Xianshun Zeng, Langxing Chen, Xuebing Leng, Fengbo Xu, Qinshan Li, Xiwen He, Wenqin Zhang, Zheng-Zhi Zhang

2003-02-25 Paper

DOI: 10.1039/B211381C

Tuning the keto equilibrium in 4-substituted dipicolinic acid derivatives

Anne-Sophie Chauvin, Sandrine Gras, Jean-Claude G. Bünzli

2003-01-22 Paper

DOI: 10.1039/B211267C

You might also like

Compound Q&A

How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?

2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...

615-45-22-Methylbenzene-1,4-...
Compound Q&A

Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...

132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A

What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?

(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...

871826-15-2(6-Chloropyridazin-3...
Compound Q&A

What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?

2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...

77772-72-62-Fluoro-3-methylphe...
Compound Q&A

What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?

When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...

177476-75-43-Methoxy-4-nitroben...
Compound Q&A

What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?

When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...

211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A

What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?

4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...

90347-86-74-Ethynylbenzamide
Compound Q&A

What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?

3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...

186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A

What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?

(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...

500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A

What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?

Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...

102196-18-92-[4-(Hydroxymethyl)...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.