4679-81-6Relevant articles and documents
UNUSUAL AROMATIC HYDROXYLATION IN THE PHOTOOXYGENATION OF 1-ISOPROPYLIDENE-2-INDANONE AND RELATED COMPOUNDS
Ensley, Harry E.,Balakrishnan, P.,Hogan, Christopher
, p. 1625 - 1628 (1989)
1-Isopropylidene-2-indanone (1) reacts with singlet oxygen in non-nucleophilic solvents to give the epoxyphenol 3.Compound 3 can be deoxygenated by treatment with P(OR)3, to afford the regiospecifically hydroxylated phenol 5.
A practical variation on the Leuckart reaction
Tournier, Lucie,Zard, Samir Z.
, p. 971 - 973 (2005)
S-Aryldiazo xanthates, derived from the corresponding diazonium salts by reaction with potassium O-ethyl xanthate, undergo a radical chain reaction with loss of nitrogen; the intermediate aromatic radical can be captured by an internal olefin to give bicy
Visible light induced hydrodifluoromethylation of alkenes derived from oxindoles with (difluoromethyl)triphenylphosphonium bromide
Hu, Wei-Qiang,Xu, Xiu-Hua,Qing, Feng-Ling
, p. 73 - 79 (2018/02/09)
A visible light induced hydrodifluoromethylation of alkenes derived from oxindoles with (difluoromethyl)triphenylphosphonium bromide was developed. This reaction delivers a series of previously unknown difluoromethylated oxindoles containing C–CF2H quaternary centers in moderate to excellent yields. The resulting CF2H-containing oxindoles are potentially useful in drug discovery.
Regio- and diastereoselective vinylogous Mannich addition of 3-alkenyl-2-oxindoles to α-fluoroalkyl aldimines
Liu, Yingle,Yang, Yi,Huang, Yangen,Xu, Xiu-Hua,Qing, Feng-Ling
supporting information, p. 67 - 72 (2015/02/19)
An efficient asymmetric vinylogous Mannich (AVM) addition reaction of 3-alkenyl-2-oxindoles to α-fluoroalkyl aldimines has been developed. This reaction provided various optical active α-alkylidene-δ-amino-δ-fluoroalkyl oxindoles in excellent yields, complete γ-site regioselectivity, and excellent diastereoselectivities.
Reductive coupling of isatins with ketones and aldehydes by low-valent titanium
Kise, Naoki,Sasaki, Kouta,Sakurai, Toshihiko
, p. 9668 - 9675 (2015/01/08)
The reductive coupling of isatins with ketones and aldehydes by Zn-TiCl4 in THF gave two- and four-electron reduced products, 3-hydoxy-3-(1-hydoxyalkyl)oxindoles and 3-alkylideneoxindoles, selectively by controlling the reaction conditions. Alt
Synthesis of spiro[furan-3,3′-indolin]-2′-ones by PET-catalyzed [3+2] reactions of spiro[indoline-3,2′-oxiran]-2-ones with electron-rich olefins
Wang, Lihong,Li, Zhanshan,Lu, Lianhong,Zhang, Wei
supporting information; experimental part, p. 1483 - 1491 (2012/03/09)
An efficient procedure for the synthesis of spiro[furan-3,3′-indolin] -2-ones and dispiro[cycloalkane-1,2′-furan-3′,3″-indolin]- 2″-ones has been achieved in high yields and stereoselectivity by photoinduced electron transfer-catalyzed [3+2] reactions of substituted spiro[indoline-3,2′-oxiran]-2-ones with olefins. The reactions proceed by ring opening of spiro[indoline-3,2′-oxiran]-2-ones via C β-O bond cleavage and subsequent cycloaddition with olefins by using 2,4,6-triphenylpyrylium tetarfluoroborate (TPT) as a sensitizer.
A comparison of the photosensitized rearrangement and the Lewis-acid-catalyzed rearrangement of spirooxindole epoxides
Wang, Lihong,Su, Yibing,Xu, Xinmin,Zhang, Wei
supporting information, p. 6606 - 6611 (2013/01/15)
Spirooxindole epoxides undergo smooth rearrangement either under photosensitization conditions or under Lewis acid catalysis to give different products. The photosensitized rearrangement of spirooxindole epoxides leads to 3-acyl-2-indolones, such as spiro
Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: Reaction development and applications
Trost, Barry M.,Zhang, Yong
supporting information; experimental part, p. 2916 - 2922 (2011/05/02)
We report a full account of our work towards the development of Mo-catalyzed asymmetric allylic alkylation reactions with 3-alkyloxindoles as nucleophiles. The reaction is complementary to the Pd-catalyzed reaction with regard to the scope of oxindole nucleophiles. A number of 3-alkyloxindoles were alkylated successfully under mild conditions to give products with excellent yields and good-to-excellent enantioselectivities. Applications of this method to the preparation of indoline alkaloids such as (-)-physostigmine, ent-(-)-debromoflustramine B, and the indolinoquinoline rings of communesin B are reported.
Photoinduced Cyclizations of Mono- and Dianions of N-Acyl-o-chloroanilines and N-Acyl-o-chlorobenzylamines as General Methods for the Synthesis of Oxindoles and 1,4-Dihydro-3(2H)-isoquinolinones
Goehring, R. Richard,Sachdeva, Yesh P.,Pisipati, Jyothi S.,Sleevi, Mark C.,Wolfe, James F.
, p. 435 - 443 (2007/10/02)
Formation of the monoanions of a series of N-acyl-N-alkyl-o-chloroanilines by means of LDA in THF followed by irradiation with near-UV light affords 1,3-dialkyloxindoles in good yields.Similar photoinduced cyclizations of dianions derived from N-acyl-o-chloroanilines leads to 3-alkyloxindoles.Photocyclizations of mono- and dianion prepared from α,β-unsaturated o-haloanilides proceed to form 3-alkylideneoxindoles.Carbanions derived from N-acyl-o-chlorobenzylamines also undergo photoassisted ring closure to afford 1,4-dihydro-3(2H)-isoquinolinones.The influence of near-UV light and the effect of inhibitors implicate a radical-chain mechanism as the major reaction pathway in this convenient new method for oxindole and isoquinolinone synthesis.
