Cascade radical cyclization on 3-propargyl-2-alkenyl indole gives stereoselective access to cyclohepta[b]indole over carbazole
Literature Information
Publication Date
2023-11-27
DOI
10.1039/D3CC05237K
Impact Factor
6.222
Authors
Santosh J. Gharpure, Sanyog Kumari
View Original
Abstract
A protecting group-dependent diastereoselective synthesis of cyclohepta[b]indole over carbazole derivatives is developed. This strategy involves a regioselective 6-exo-trig radical cyclization-cyclopropanation-ring expansion cascade of 3-propargyl-2-alkenyl indole. The cascade radical cyclization was also performed on indole derivatives possessing alkyne, acrylate and vinylogous carbamate moieties, which delivered pyridocarbazole giving credence to the mechanistic hypothesis. Furthermore, cyclohepta[b]indole could be selectively converted to sulfone and sulfoxide as well as benzoazulenoindole via intramolecular Friedel–Crafts acylation.
Related Literature
Influence of surface charge on the formulation of elongated PEG-b-PDLLA nanoparticles
Roxane Ridolfo, David S. Williams, Jan C. M. van Hest
2020-03-31
Communication
DOI: 10.1039/D0PY00280A
Tacticity dependence of single chain polymer folding
Denis Danilov, Elaheh Sedghamiz, Heike Fliegl, Wolfgang Wenzel
2020-04-14
Paper
DOI: 10.1039/D0PY00133C
A 3D printed drug delivery implant formed from a dynamic supramolecular polyurethane formulation
S. Salimi, Y. Wu, M. I. Evangelista Barreiros, A. A. Natfji, S. Khaled, R. Wildman, L. R. Hart, F. Greco, E. A. Clark, C. J. Roberts, W. Hayes
2020-04-21
Paper
DOI: 10.1039/D0PY00068J
Assembly of miscible supramolecular network blends using DDA·AAD hydrogen-bonding interactions of pendent side-chains
Heather M. Coubrough, Matthew Reynolds, James A. Goodchild, Simon D. A. Connell, Johan Mattsson
2020-05-12
Paper
DOI: 10.1039/C9PY01913H
Rapid metal-free synthesis of pyridyl-functionalized conjugated microporous polymers for visible-light-driven water splitting
Zhonghua Cheng, Lei Wang, Yan He, Xingjia Chen, Xiaojun Wu, Hangxun Xu, Yaozu Liao, Meifang Zhu
2020-04-14
Communication
DOI: 10.1039/D0PY00249F
Temporal control of RAFT polymerization via magnetic catalysis
Amin Reyhani, Masood S. Alivand, Kathryn A. Mumford, Greg Qiao
2020-03-16
Paper
DOI: 10.1039/D0PY00220H
Effects of tacticity and chiral center-to-dipole distance on mesogen-free liquid crystalline self-assembly of sulfonyl-containing comb-like polymers
Caleb A. Bohannon, Man-Hin Kwok, Ruipeng Li, Lei Zhu, Bin Zhao
2020-03-30
Paper
DOI: 10.1039/D0PY00199F
Metallopolymer-block-oligosaccharide for sub-10 nm microphase separation
Satoshi Katsuhara, Hiroaki Mamiya, Takuya Yamamoto, Kenji Tajima, Takuya Isono, Toshifumi Satoh
2020-03-31
Paper
DOI: 10.1039/D0PY00271B
Alkene–azide chemistry: a facile, one-step, solvent- and catalyst-free approach for developing new functional monomers and polymers
Santimukul Santra, Ren Bean, Blaze Heckert, Zachary Shaw, Vedant Jain, Lok Shrestha, Raghunath Narayanam, Quentin Austin
2020-05-07
Paper
DOI: 10.1039/D0PY00346H
You might also like
Compound Q&A
How should waste containing 6-Chloro-5-(2'-hydroxy-3'-methoxy-4-biphenylyl)-3-(3-methoxyphenyl)-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (CAS: 1346607-05-3) be handled?
Waste containing 6-Chloro-5-(2'-hydroxy-3'-methoxy-4-biphenylyl)-3-(3-methoxyphe...
1346607-05-36-Chloro-5-(2'-hydro...
Compound Q&A
What are the main uses of (3alpha,5alpha)-3-Hydroxypregnane-11,20-dione (CAS: 23930-19-0)?
(3alpha,5alpha)-3-Hydroxypregnane-11,20-dione is primarily used in the pharmaceu...
23930-19-0(3alpha,5alpha)-3-Hy...
Compound Q&A
What is the market or research trend for 4-Amino-6-chloro-2-pyridinecarboxylic acid (CAS: 546141-56-4)?
The market for 4-Amino-6-chloro-2-pyridinecarboxylic acid (CAS: 546141-56-4) is ...
546141-56-44-Amino-6-chloro-2-p...
Compound Q&A
Are there alternatives to (2-Benzoylethyl)trimethylammonium chloride (CAS: 24472-88-6) in synthesis?
Alternatives to (2-Benzoylethyl)trimethylammonium chloride (CAS: 24472-88-6) in ...
24472-88-6(2-Benzoylethyl)trim...
Compound Q&A
Is N-[4-Nitro-3-(trifluoromethyl)phenyl]acetamide (CAS: 393-12-4) safe?
N-[4-Nitro-3-(trifluoromethyl)phenyl]acetamide (CAS: 393-12-4) is generally safe...
393-12-4N-[4-Nitro-3-(triflu...
Compound Q&A
Are there alternatives to [(4R,5R,6S)-5-hydroxy-10-imino-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-4-yl]methyl dihydrogen phosphate (CAS: 39679-56-6) in synthesis?
Alternative reagents such as other phosphates or similar functional groups can b...
39679-56-6[(4R,5R,6S)-5-hydrox...
Compound Q&A
Are there alternatives to N,N'-Bis(3-aminopropyl)-1,3-propanediamine (CAS: 4605-14-5) in synthesis?
There are alternatives to N,N'-Bis(3-aminopropyl)-1,3-propanediamine (CAS: 4605-...
4605-14-5N,N'-Bis(3-aminoprop...
Compound Q&A
What precautions should be taken when handling Aluminium trihexadecanoate (CAS: 555-35-1)?
When handling Aluminium trihexadecanoate, it is important to use appropriate per...
555-35-1Aluminium trihexadec...
Compound Q&A
What is (1,1-Dioxido-3-oxo-1,2-benzothiazol-2(3H)-yl)acetic acid (CAS: 52188-11-1)?
(1,1-Dioxido-3-oxo-1,2-benzothiazol-2(3H)-yl)acetic acid is a chemical compound ...
52188-11-1(1,1-Dioxido-3-oxo-1...
Compound Q&A
Are there alternatives to 5,5-dimethyloxolan-2-one (CAS: 3123-97-5) in synthesis?
Several alternatives to 5,5-dimethyloxolan-2-one (CAS: 3123-97-5) can be used in...
3123-97-55,5-dimethyloxolan-2...
Source Journal
Chemical Communications
CiteScore:
8.6
Self-citation Rate:
4.7%
Articles per Year:
2458
ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular Chemistry
Recommended Compounds
![2-Methyl-2-propanyl (2E)-5-chloro-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]pentanoate structure](https://static.chemtradehub.com/structs/122/1225232-42-7-ee03.webp "2-Methyl-2-propanyl (2E)-5-chloro-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]pentanoate structure")
2-Methyl-2-propanyl (2E)-5-chloro-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]pentanoate
CAS Number:
1225232-42-7
Molecular Formula:
C21H27ClN2O3
![Benzyl 2-{[(tert-butoxy)carbonyl]amino}acetate structure](https://static.chemtradehub.com/structs/542/54244-69-8-6399.webp "Benzyl 2-{[(tert-butoxy)carbonyl]amino}acetate structure")
tert-Butyl 4-chloro-5-methoxypyridin-3-ylcarbamate
CAS Number:
1045858-17-0
Molecular Formula:
C11H15ClN2O3
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.