- Reductive aromatization of oxindoles to 3-substituted indoles
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A practical and scalable approach for the synthesis of 3-substituted indoles is delineated via hydride nucleophilic addition to 3-substituted-2-oxindoles. The reaction proceeds through reductive aromatization involving indolinium ion intermediate. A wide range of 3-functionalized indoles have been synthesized. The method is employed for the synthesis of 3,3?-bis-indoles and a dimeric 3-indole derivative. Moreover, this protocol is used to obtain naturally occuring amino acid tryptamine.
- Mandal, Tirtha,Chakraborti, Gargi,Dash, Jyotirmayee
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- Synthesis of 3-ethynyl-3-hydroxy-2-oxindoles and 3-hydroxy-3-(indol-3-yl) indolin-2-ones using CuWO4 nanoparticles as recyclable heterogeneous catalyst in aqueous medium
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A simple method for the direct activation of phenyl acetylenes (spC-H activation) and selective synthesis of 3-hydroxy-3-(indol-3-yl) indolin-2-ones and 3,3′-bis(indolyl)indolin-2-ones (via Friedel-Crafts alkylation reaction) is reported in presence of Cu
- Paplal, Banoth,Sathish, Kota,Nagaraju, Sakkani,Kashinath, Dhurke
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- 3-Hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one as a versatile intermediate for retro-Henry and Friedel-Crafts alkylation reactions in aqueous medium
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The first example of a retro-Henry type reaction is reported using 3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-ones which are prepared via catalyst-free Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin. These compounds were used
- Nagaraju, Sakkani,Sathish, Kota,Paplal, Banoth,Satyanarayana, Neeli,Kashinath, Dhurke
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supporting information
p. 14045 - 14050
(2019/09/18)
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- Thiourea-Catalyzed Enantioselective Malonate Addition onto 3-Sulfonyl-3′-indolyl-2-oxindoles: Formal Total Syntheses of (-)-Chimonanthine, (-)-Folicanthine, and (+)-Calycanthine
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A general approach to bispyrroloindolines via a key thiourea-catalyzed addition of malonates to 3-sulfonyl-3′-indolyl-2-oxindoles is reported. The enantioselelective process is found to be highly effective (up to 94% ee), where a C-C bond formation leads
- Babu, K. Naresh,Roy, Avishek,Singh, Manvendra,Bisai, Alakesh
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supporting information
p. 6327 - 6331
(2018/10/20)
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- The first synthesis of cis-N,N′-dialkylisoindigo derivatives from 3-indolyl-2-oxindoles with DDQ
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cis-N,N′-Dialkylisoindigo derivatives were synthesized for the first time by the reaction of 3-indolyl-2-oxindoles with DDQ in aqueous 1,4-dioxane. cis-Isoindigo derivatives were completely isomerized to the corresponding trans-isomers by heating the solu
- Seo, Da Young,Roh, Hwa Jung,Jo, Hwi Yul,Cho, Sung,Kim, Jae Nyoung
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supporting information
p. 1005 - 1009
(2018/02/23)
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- Experimental and theoretical investigations of regioselective functionalization of 3-hydroxy bisindoles with thiols
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An instant and efficient p-TSA·H2O-catalyzed sulfenylation reaction of 3-hydroxy bisindole derivatives is reported. This highly regioselective approach afforded C-3 functionalized products in excellent yield, and this methodology was found to b
- Sharma, Nitika,Peddinti, Rama Krishna
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supporting information
p. 9259 - 9268
(2019/01/03)
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- FeCl3-Catalyzed Allylation Reactions onto 3-Hydroxy-2-oxindoles: Formal Total Syntheses of Bis-cyclotryptamine Alkaloids, (±)-Chimonanthine, and (±)-Folicanthine
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An FeCl3-catalyzed efficient strategy for the allylation reactions of 3-hydroxy-2-oxindoles with allyltrimethylsilane has been developed. The reaction affords a variety of 2-oxindoles having quaternary center at the pseudobenzylic position in an operationally simple and inexpensive procedure. Control experiments using enantioenriched 3-hydroxy-2-oxindole show that the reaction proceeds through in situ generated 2H-indol-2-one (8). The methodology presents an efficient and concise access to the pyrroloindoline alkaloids (±)-deoxyeseroline (1a), (±)-esermethole (1b), (±)-physostigmine (1c), (±)-phenserine (1d), and (±)-physovenine (1e). Eventually, we extrapolated the scope of this methodology to the formal total syntheses of dimeric cyclotyrptamine alkaloids (±)-chimonanthine (3a), (±)-folicanthine (3c), and (±)-calycanthine (4).
- Kinthada, Lakshmana K.,Medisetty, Sai Raghavendra,Parida, Amarchand,Babu, K. Naresh,Bisai, Alakesh
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p. 8548 - 8567
(2017/08/23)
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- 5,5′-Bistriazoles as axially chiral, multidentate ligands: Synthesis, configurational stability and catalytic application of their scandium(iii) complexes
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The design and development of 5,5′-bistriazoles featuring aminomethyl substituents is discussed. An efficient synthetic procedure for the selective preparation of 4,4′-bis(aminomethyl)-5,5′-bistriazoles from commercially available propargylamine derivativ
- Etayo, Pablo,Escudero-Adán, Eduardo C.,Pericàs, Miquel A.
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p. 4830 - 4841
(2017/10/19)
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- Tf2NH-Catalyzed Amide Synthesis from Vinyl Azides and Alcohols
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Triflimide (Tf2NH) specifically catalyzed reactions of alcohols and vinyl azides, enabling efficient construction of amides with C-C bond formation through nucleophilic attack of vinyl azides onto the putative carbocation intermediates derived from alcohols are described.
- Zhang, Feng-Lian,Zhu, Xu,Chiba, Shunsuke
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supporting information
p. 3138 - 3141
(2015/06/30)
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- Catalytic Enantioselective Decarboxylative Allylations of a Mixture of Allyl Carbonates and Allyl Esters: Total Synthesis of (-)- and (+)-Folicanthine
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A highly enantioselective decarboxylative allylation of a mixture of enol carbonates and allyl esters has been achieved. The strategic viability of this methodology has been demonstrated through the total synthesis of cyclotryptamine alkaloids (-)- and (+)-folicanthine (1 a) and the formal total synthesis of (-)-chimonanthine (1 b), (+)-calycanthine (1 c), and (-)-ditryptophenaline (1 d).
- Ghosh, Santanu,Chaudhuri, Saikat,Bisai, Alakesh
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supporting information
p. 17479 - 17484
(2016/01/25)
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- "on water" expedient synthesis of 3-indolyl-3-hydroxy oxindole derivatives and their anticancer activity in vitro
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A series of 3-indolyl-3-hydroxy oxindole derivatives (n = 41) were synthesized by the green aminocatalytic method with excellent yields under mild reaction conditions. All the newly synthesized derivatives were subjected to evaluate their cytotoxic proper
- Sai Prathima, Parvathaneni,Rajesh, Pamanji,Venkateswara Rao, Janapala,Sai Kailash, Uppalapati,Sridhar, Balasubramanian,Mohan Rao, Mandapati
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supporting information
p. 155 - 159
(2014/07/22)
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- Kaolin/KOH is an efficient heterogeneous catalyst for the synthesis of 3-hydroxy-3-indolyl oxindoles
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3-Hydroxy-3-indolyl oxindoles were synthesized from isatins and indoles in good to excellent yields by using heterogeneous catalyst kaolin preloaded with KOH. Taylor & Francis Group, LLC.
- Srihari,Murthy, M. Marthanda
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experimental part
p. 2684 - 2692
(2011/08/05)
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