Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines
Literature Information
Alexander V. Aksenov, Dmitrii A. Aksenov, Nicolai A. Aksenov, Leonid G. Voskressensky
The polyphosphoric acid-mediated reaction of 2-(2-aminophenyl)indenes with nitroalkenes was tested in the frame of synthetic studies towards CDK inhibitors with the paullone core. Unexpectedly, this reaction proceeded via a different mechanistic pathway affording derivatives of the natural alkaloid isocryptolepine. The scope of this unusual transformation was investigated and a mechanistic rationale explaining this outcome is offered.
Recommended Journals

Atomization and Sprays

Electroanalysis

Medicinal Chemistry Research

Main Group Chemistry

Critical Reviews in Solid State and Materials Sciences

Journal of Chemical Sciences

Heteroatom Chemistry

Journal of Asian Natural Products Research

Polycyclic Aromatic Compounds

Journal of the Indian Institute of Science
Related Literature
Palladium-catalyzed enantioselective [5 + 4] annulation of ortho-quinone methides and vinylethylene carbonates
Chao Xia, Dong-Chao Wang, Gui-Rong Qu
DOI: 10.1039/D0QO00128G
Bicyclic acetals: biological relevance, scaffold analysis, and applications in diversity-oriented synthesis
Elena Lenci, Fernanda I. Saldívar-Gonzalez, José L. Medina-Franco
DOI: 10.1039/C8OB02808G
Access to cyano-substituted pyrazolines through copper-catalyzed cascade cyanation/cyclization of unactivated olefins
Fei Meng, Qin Fang, Weidong Yuan, Ning Xu, Shujun Cao, Jianlin Chun, Jie Li, Honglin Zhang, Yingguang Zhu
DOI: 10.1039/D0QO00282H
A semipinacol rearrangement of vinylogous α-ketol cocatalyzed by a cinchona-based primary amine and N-Boc-phenylglycines: mechanisms, roles of catalysts and the origin of enantioselectivity
Chao-Xian Yan, Fang-Ling Yang, Ka Lu, Xing Yang, Pan-Pan Zhou, Xiangfeng Shao
DOI: 10.1039/D0QO00506A
Design, synthesis and glycosidase inhibition studies of novel triazole fused iminocyclitol-δ-lactams
Venkatesan Santhanam, Pradeep Pant, B. Jayaram, Namakkal G. Ramesh
DOI: 10.1039/C8OB03084G
Organocatalytic 1,5-trifluoromethylthio-sulfonylation of vinylcyclopropane mediated by visible light in the water phase
Junkai Liu, Hong Yao, Xinnan Li, Hongyu Wu, Aijun Lin, Hequan Yao, Jinyi Xu, Shengtao Xu
DOI: 10.1039/D0QO00343C
Chiral strong Brønsted acid-catalyzed enantioselective addition reaction of simple olefins with ethyl glyoxylate
Jun Kikuchi, Yuki Aizawa, Masahiro Terada
DOI: 10.1039/D0QO00448K
One-pot stapling of interchain disulfides of antibodies using an isobutylene motif
Shuang Sun, Padma Akkapeddi, Nuria Martínez-Sáez, Vukosava M. Torres, Carlos Cordeiro, Omar Boutureira
DOI: 10.1039/C8OB02877J
You might also like
What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?
(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...
What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?
When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...
Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?
There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...
What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?
1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...
Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?
Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...
What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?
2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...
How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?
Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...
How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?
2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...
What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?
Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...
Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?
In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...
Source Journal
Organic & Biomolecular Chemistry

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.
![N,N'-1,2-Ethanediylbis[2-(vinylsulfonyl)acetamide] structure N,N'-1,2-Ethanediylbis[2-(vinylsulfonyl)acetamide] structure](https://static.chemtradehub.com/structs/667/66710-66-5-b556.webp)

![N-[(5,6-Dichloro-1H-benzimidazol-2-yl)methyl]-9-(1-methyl-1H-pyrazol-4-yl)-2-(4-morpholinyl)-9H-purin-6-amine structure N-[(5,6-Dichloro-1H-benzimidazol-2-yl)methyl]-9-(1-methyl-1H-pyrazol-4-yl)-2-(4-morpholinyl)-9H-purin-6-amine structure](https://static.chemtradehub.com/structs/238/2387704-62-1-25f4.webp)

