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Indium/Fe( iii ) mediated regioselective -cross-coupling aldol type addition reaction of activated alkenes with isatins/isatinimines in aqueous media

A highly efficient and regioselective -cross coupling aldol type addition reaction of activated alkenes with isatin/isatinimine derivatives in the presence of Indium/Fe( iii ) in THF/H 2 O at room temperature is described. Our synthetic protocol explores a broad substrate scope and smoothly proceeds... Full description

Journal Title: RSC Advances 2015, Vol.5(64), pp.51581-51585
Main Author: Kumar, A. Sanjeeva
Other Authors: Ramesh, Palakuri , Kumar, G. Santosh , Nanubolu, Jagadeesh Babu , Rao, T. Prabhakar , Meshram, H. M.
Format: Electronic Article Electronic Article
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ID: ISSN: 2046-2069 ; DOI: 10.1039/c5ra07216f
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title: Indium/Fe( iii ) mediated regioselective -cross-coupling aldol type addition reaction of activated alkenes with isatins/isatinimines in aqueous media
format: Article
creator:
  • Kumar, A. Sanjeeva
  • Ramesh, Palakuri
  • Kumar, G. Santosh
  • Nanubolu, Jagadeesh Babu
  • Rao, T. Prabhakar
  • Meshram, H. M.
subjects:
  • Reaction Time
  • Joining
  • Media
  • Derivatives
  • Indium
  • Alkenes
  • Activated
  • Aldehydes
  • Chemical and Electrochemical Properties (MD)
  • Chemical and Electrochemical Properties (Ep)
  • Chemical and Electrochemical Properties (Ed)
  • Chemical and Electrochemical Properties (EC)
ispartof: RSC Advances, 2015, Vol.5(64), pp.51581-51585
description: A highly efficient and regioselective -cross coupling aldol type addition reaction of activated alkenes with isatin/isatinimine derivatives in the presence of Indium/Fe( iii ) in THF/H 2 O at room temperature is described. Our synthetic protocol explores a broad substrate scope and smoothly proceeds under base-free conditions. The resulting products are obtained in a short reaction time with moderate to high yields. This is the first example of Mannich-type coupling of isatinimines with activated alkenes to afford the alkyl 3-(2-oxo-3-(phenylamino)indolin-3-yl)propanoates and 3-(3-oxoalkyl)-3-(phenylamino)indolin-2-ones.
language:
source:
identifier: ISSN: 2046-2069 ; DOI: 10.1039/c5ra07216f
fulltext: fulltext
issn:
  • 2046-2069
  • 20462069
url: Link


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titleIndium/Fe( iii ) mediated regioselective -cross-coupling aldol type addition reaction of activated alkenes with isatins/isatinimines in aqueous media
creatorKumar, A. Sanjeeva ; Ramesh, Palakuri ; Kumar, G. Santosh ; Nanubolu, Jagadeesh Babu ; Rao, T. Prabhakar ; Meshram, H. M.
ispartofRSC Advances, 2015, Vol.5(64), pp.51581-51585
identifierISSN: 2046-2069 ; DOI: 10.1039/c5ra07216f
descriptionA highly efficient and regioselective -cross coupling aldol type addition reaction of activated alkenes with isatin/isatinimine derivatives in the presence of Indium/Fe( iii ) in THF/H 2 O at room temperature is described. Our synthetic protocol explores a broad substrate scope and smoothly proceeds under base-free conditions. The resulting products are obtained in a short reaction time with moderate to high yields. This is the first example of Mannich-type coupling of isatinimines with activated alkenes to afford the alkyl 3-(2-oxo-3-(phenylamino)indolin-3-yl)propanoates and 3-(3-oxoalkyl)-3-(phenylamino)indolin-2-ones.
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subjectReaction Time ; Joining ; Media ; Derivatives ; Indium ; Alkenes ; Activated ; Aldehydes ; Chemical and Electrochemical Properties (MD) ; Chemical and Electrochemical Properties (Ep) ; Chemical and Electrochemical Properties (Ed) ; Chemical and Electrochemical Properties (EC);
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titleIndium/Fe( iii ) mediated regioselective -cross-coupling aldol type addition reaction of activated alkenes with isatins/isatinimines in aqueous media
descriptionA highly efficient and regioselective -cross coupling aldol type addition reaction of activated alkenes with isatin/isatinimine derivatives in the presence of Indium/Fe( iii ) in THF/H 2 O at room temperature is described. Our synthetic protocol explores a broad substrate scope and smoothly proceeds under base-free conditions. The resulting products are obtained in a short reaction time with moderate to high yields. This is the first example of Mannich-type coupling of isatinimines with activated alkenes to afford the alkyl 3-(2-oxo-3-(phenylamino)indolin-3-yl)propanoates and 3-(3-oxoalkyl)-3-(phenylamino)indolin-2-ones.
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titleIndium/Fe( iii ) mediated regioselective -cross-coupling aldol type addition reaction of activated alkenes with isatins/isatinimines in aqueous media
authorKumar, A. Sanjeeva ; Ramesh, Palakuri ; Kumar, G. Santosh ; Nanubolu, Jagadeesh Babu ; Rao, T. Prabhakar ; Meshram, H. M.
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abstractA highly efficient and regioselective -cross coupling aldol type addition reaction of activated alkenes with isatin/isatinimine derivatives in the presence of Indium/Fe( iii ) in THF/H 2 O at room temperature is described. Our synthetic protocol explores a broad substrate scope and smoothly proceeds under base-free conditions. The resulting products are obtained in a short reaction time with moderate to high yields. This is the first example of Mannich-type coupling of isatinimines with activated alkenes to afford the alkyl 3-(2-oxo-3-(phenylamino)indolin-3-yl)propanoates and 3-(3-oxoalkyl)-3-(phenylamino)indolin-2-ones.
doi10.1039/c5ra07216f
pages51581-51585
date2015-06-11