Construction of diverse spirooxindoles via a domino reaction of arylamines, but-2-ynedioates and 3-hydroxy-3-(indol-3-yl)indolin-2-ones
Literature Information
Ling-Yun Zhu, Jing Sun, Dan Liu, Chao-Guo Yan
An iodine-promoted domino reaction of arylamines/benzylamines, dialkyl but-2-ynedioates and 3-hydroxy-3-(indol-3-yl)indolin-2-ones showed very interesting molecular diversity. The reaction in acetonitrile at 65 °C in the presence of 30% mmol I2 resulted in spiro[indoline-3,1′-pyrido[4,3-b]indoles] in satisfactory yields. When anilines without para-substituents were used in the reaction, a direct substitution of the hydroxyl group to 2-(phenylamino)maleate at the para-position of aniline gave chain products in good yields. Additionally, similar reactions with benzylamines not only gave spiro[indoline-3,1′-pyrido[4,3-b]indoles], but also afforded spiro[indoline-3,1′-pyrano[4,3-b]indol]-2-ones in lower yields. A plausible domino annulation mechanism was rationally proposed for the formation of different kinds of polycyclic compounds.
Related Literature
HIV-1 protease: mechanism and drug discovery
Ashraf Brik, Chi-Huey Wong
DOI: 10.1039/B208248A
Dirhodium(ii)-catalyzed ortho C–H amination of sterically congested N,N-dialkylanilines
Motoki Ito, Tomoya Nakagawa, Kazuhiro Higuchi, Shigeo Sugiyama
DOI: 10.1039/C8OB01974F
Cyclopropanation of alkenes with metallocarbenes generated from monocarbonyl iodonium ylides
Tristan Chidley, Graham K. Murphy
DOI: 10.1039/C8OB02636J
Studies of 4-arylthiazolylhydrazones derived from 1-indanones as Trypanosoma cruzi squalene epoxidase inhibitors by molecular simulations
Lucas E. Fabian
DOI: 10.1039/C8OB02310G
Antitumor benzothiazoles. Frontier molecular orbital analysis predicts bioactivation of 2-(4-aminophenyl)benzothiazoles to reactive intermediates by cytochrome P4501A1
Sean E. O'Brien, Helen L. Browne, Tracey D. Bradshaw, Andrew D. Westwell, Malcolm F. G. Stevens, Charles A. Laughton
DOI: 10.1039/B209067H
Direct determination of single-to-double stranded DNA ratio in solution using steady-state fluorescence measurements
Lori Beach, Claude Schweitzer, J. C. Scaiano
DOI: 10.1039/B209284K
Novel 3-phenylprop-2-ynylamines as inhibitors of mammalian squalene epoxidase
David L. Musso, Morris J. Clarke, James L. Kelley, G. Evan Boswell, Grace Chen
DOI: 10.1039/B209165H
Resolution of the non-steady-state kinetics of the elimination of HBr from 2-(p-nitrophenyl)ethyl bromide in alcohol/alkoxide media
Kishan L. Handoo, Yun Lu, Yixing Zhao, Vernon D. Parker
DOI: 10.1039/B208634D
New strategies and building blocks for functionalised 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene derivatives, including pyrrolo-annelated derivatives and π-extended systems with intramolecular charge-transfer‡
Christian A. Christensen, Martin R. Bryce, Andrei S. Batsanov, Jan Becher
DOI: 10.1039/B211153P
Origins of the enantioselectivity of a palladium catalyst with BINOL–phosphoric acid ligands
DOI: 10.1039/C8OB02271B
You might also like
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 ...
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...
What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?
(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...
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...
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...
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 ...
What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?
4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...
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...
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...
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...
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.











![Methyl 2-[5-(3-Phenoxyphenyl)-2H-tetrazol-2-yl]acetate structure Methyl 2-[5-(3-Phenoxyphenyl)-2H-tetrazol-2-yl]acetate structure](https://static.chemtradehub.com/structs/130/1305320-60-8-84b4.webp)
![trans-2-{[(Tert-butoxy)carbonyl]amino}cyclobutane-1-carboxylic acid structure trans-2-{[(Tert-butoxy)carbonyl]amino}cyclobutane-1-carboxylic acid structure](https://static.chemtradehub.com/structs/951/951173-25-4-27cd.webp)

