1969-74-0Relevant articles and documents
Dual Catalysis for the Redox Annulation of Nitroalkynes with Indoles: Enantioselective Construction of Indolin-3-ones Bearing Quaternary Stereocenters
Liu, Ren-Rong,Ye, Shi-Chun,Lu, Chuan-Jun,Zhuang, Gui-Lin,Gao, Jian-Rong,Jia, Yi-Xia
, p. 11205 - 11208 (2015)
The enantioselective redox annulation of nitroalkynes with indoles is enabled by gold/chiral phosphoric acid dual catalysis. A range of indolin-3-one derivatives bearing quaternary stereocenters at the C2 position were afforded in good yields and excellen
Intermolecular Interception of α-Oxo Gold Carbenes of Nitroalkyne Cycloisomerization with 1,2-Benzo[ d]isoxazole: Synthesis of Functionalized Quinazoline 1-Oxides
Dhote, Pawan S.,Pund, Kishor A.,Ramana, Chepuri V.
, p. 10874 - 10882 (2021)
The known nitrogen-transfer reagent 1,2-benzo[d]isoxazole has been used to trap the postulated α-oxo gold carbene intermediate involved in the [Au]-catalyzed internal redox process of 2-alkynylnitrobenzenes. This process led us to develop a general conver
One-Pot Synthesis of Fused Indolin-3-Ones via a [3+3] Cycloaddition Reaction
Huang, Lang,Yao, Zhenyu,Huang, Guanghua,Ao, Yaqi,Zhu, Bin,Li, Sanshu,Cui, Xiuling
supporting information, p. 5092 - 5098 (2021/09/25)
A formal [3+3] cycloaddition reaction of azaoxyallyl cations and isatogens generated in situ from α-halo hydroxamates and o-nitroalkynes, respectively, was developed. The cycloisomerization of the o-nitroalkynes, followed by base-mediated elimination of h
Regioselective Cross-Coupling of Isatogens with Boronic Acids to Construct 2,2-Disubstituted Indolin-3-one Derivatives
Song, Qiuling,Xu, Hetao,Yang, Kai,Ye, Mingxing
supporting information, p. 7776 - 7780 (2021/10/25)
Herein we present a transition-metal-free cross-coupling reaction of isatogens with boronic acids through a 1,4-metalate shift of a boron "ate"complex. This coupling reaction provides a feasible method to deliver valuable 2,2-disubstituted indolin-3-one d
Catalytic asymmetric formal [3+2] cycloaddition of isatogens with azlactones to construct indolin-3-one derivatives
Xie, Lihua,Li, Yi,Dong, Shunxi,Feng, Xiaoming,Liu, Xiaohua
supporting information, p. 239 - 242 (2021/01/14)
The chiral amide-guanidine-catalyzed asymmetric formal [3+2] cycloaddition of isatogens with azlactones is presented. This strategy provided a facile and feasible route to chiral indolin-3-one derivatives bearing two contiguous tetrasubstituted stereocent
One-Pot Au[III]-/Lewis Acid Catalyzed Cycloisomerization of Nitroalkynes and [3 + 3]Cycloaddition with Donor-Acceptor Cyclopropanes
Dhote, Pawan S.,Ramana, Chepuri V.
supporting information, p. 6221 - 6224 (2019/08/26)
A one-pot protocol for the synthesis of a tricyclic pseudoindoxyl scaffold from 2-nitroalkynylbenzenes, comprising of an Au(III)-catalyzed nitroalkyne cycloisomerization leading to isatogen and its [3 + 3]-cycloaddition with donor-acceptor cyclopropanes m
CuH-Catalyzed Synthesis of 3-Hydroxyindolines and 2-Aryl-3H-indol-3-ones from o-Alkynylnitroarenes, Using Nitro as Both the Nitrogen and Oxygen Source
Peng, Hui,Ma, Jinhui,Duan, Lingfei,Zhang, Guangwen,Yin, Biaolin
supporting information, p. 6194 - 6198 (2019/08/20)
CuH-catalyzed diasterospecific synthesis of 3-hydroxyindolines and 2-aryl-3H-indol-3-ones have been developed from o-alkynylnitroarenes in the presence of hydrosilane as the reductant. The protocol employs nitro as both nitrogen and oxygen sources for the
C-H alkenylation/cyclization and sulfamidation of 2-phenylisatogens using: N -oxide as a directing group
Guo, Lingmei,Tang, Baolan,Nie, Ruifang,Liu, Yanzhao,Lv, Shan,Wang, Huijing,Guo, Li,Hai, Li,Wu, Yong
supporting information, p. 10623 - 10626 (2019/09/06)
The first example of transition-metal-catalyzed C-H activations of 2-phenylisatogens with alkynes and sulfonyl azides has been developed using N-oxide as the directing group. Ru(ii)-Catalyzed C-H alkenylation/cyclization and Ir(iii)-catalyzed direct C-H sulfamidation proceeded with good yields and excellent functional group tolerance. Importantly, these two transformations provided straightforward routes for the synthesis of indol-3-one derivatives and sulfamidated 2-phenylisatogens respectively, which might be of considerable bioactivities.
One-Pot Synthesis of Indole Derivatives from the Reaction of Nitroalkynes and Alkynes via a Mercury-Carbene Intermediate
Zheng, Min,Chen, Kai,Zhu, Shifa
, p. 4173 - 4182 (2017/09/13)
The cyclization of nitroalkyne catalyzed by Hg(OTf) 2 to produce the corresponding benzo[ c ]isoxazole in excellent yields with high selectivity is reported. On the basis of this strategy, a one-pot method to synthesize indole derivatives has been developed. In this transformation, two Hg-carbene intermediates are proposed to be involved..
2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behaviour and antiplasmodial activities
Najahi, Ennaji,Valentin, Alexis,Fabre, Paul-Louis,Reybier, Karine,Nepveu, Fran?oise
, p. 269 - 274 (2014/04/17)
The synthesis of indolone derivatives and their antiplasmodial activity in vitro against Plasmodium falciparum at the blood stage are described. The 2-aryl-3H-indol-3-ones were synthesized via deoxygenation of indolone-N-oxides. Electrochemical behaviour, antiplasmodial activity and cytotoxicity on human tumor cell lines were compared to those of indolone-N-oxides. The antiplasmodial IC50 (concentrations at 50% inhibition) of these compounds ranged between 49 and 1327 nM. Among them, the 2-(4-dimethylaminophenyl)-5-methoxy- indol-3-one, 7, had the best antiplasmodial activity in vitro (IC50 = 49 nM; FcB1 strain) and selectivity index (SI (CC50 MCF7/IC 50 FcB1) = 423.4). Thus, the hits identified in this deoxygenated series correspond to their structural homologs in the N-oxide series with comparable electrochemical behaviour at the nitrogen-carbon double bond.
