Facile Synthesis of 2-Arylindoles through Plancher-Type Rearrangement of 3-Alkyl-3-Arylindolenines

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 1994-1999
Author(s):  
Santhosh Chittimalla ◽  
Chennakesavulu Bandi ◽  
Vinod Gadi ◽  
Siva Gunturu
Keyword(s):  
Michael Addition ◽  
Facile Synthesis ◽  
Type C ◽  
High Yields

3-Alkylindoles on reaction with a cyclohexa-2,4-dien-1-one catalyzed by BF3·OEt2 gave the corresponding 3-alkyl-3-arylindolenines in high yields through a tandem Michael addition/aromatization sequence. In the presence of HCl, these indolenine derivatives underwent a facile Plancher-type C-3 to C-2 aryl rearrangement to deliver the corresponding 2-arylindoles.

scholarly journals Asymmetric Michael Addition of Malononitrile with Chalcones via Rosin-Derived Bifunctional Squaramide

Catalysts ◽  
2019 ◽  
Vol 10 (1) ◽  
pp. 14
Author(s):  
Ning Lin ◽  
Qiu-Xiang Wei ◽  
Li-Hua Jiang ◽  
Yan-Qiu Deng ◽  
Zhen-Wei Zhang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Carbonyl Compounds ◽  
Catalyst Loading ◽  
Facile Synthesis ◽  
Asymmetric Michael Addition ◽  
High Yields ◽  
Experimental Findings

A rosin-derived bifunctional squaramide catalyzed asymmetric Michael addition of malononitrile with chalcones was discovered. This protocol provides a methodology for the facile synthesis of chiral γ-cyano carbonyl compounds in high yields and enantioselectivities (up to 99% yield and 90% ee) with a lower catalyst loading (0.3 mol%). The predominant R-configured adducts were obtained by this organocatalystic reaction, according to the experimental findings.

scholarly journals Enantioselective synthesis of seven-membered carbo- and heterocyles by organocatalyzed intramolecular Michael addition

RSC Advances ◽  
2016 ◽  
Vol 6 (36) ◽  
pp. 30166-30169 ◽  
Author(s):  
James O. Guevara-Pulido ◽  
José M. Andrés ◽  
Deisy P. Ávila ◽  
Rafael Pedrosa
Keyword(s):  
Michael Addition ◽  
Enantioselective Synthesis ◽  
High Yields

Enantioenriched seven membered rings have been prepared in high yields and stereoselectivities by intramolecular Michael addition of functionalized enals catalyzed by Jorgensen–Hayashi catalyst.

Facile Synthesis of Indolines by a Tandem Nitro-reduction Aza Michael Addition Reaction

Heterocycles ◽  
2013 ◽  
Vol 87 (10) ◽  
pp. 2023 ◽  
Author(s):  
Jason Guy Taylor ◽  
Wellington Martins Ventura ◽  
Luiz Guilherme Souza de Assis
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Michael Addition Reaction ◽  
Facile Synthesis ◽  
Nitro Reduction

scholarly journals A Facile Synthesis of Polysubstituted Pyrroles by One-Pot Three-Component Reaction

2012 ◽  
Vol 9 (4) ◽  
pp. 2239-2244 ◽  
Author(s):  
Hossein Anaraki-Ardakani ◽  
Maziar Noei ◽  
Mina Karbalaei-Harofteh ◽  
Shahab Zomorodbakhsh
Keyword(s):  
Room Temperature ◽  
Facile Synthesis ◽  
One Pot ◽  
Pyrrole Derivatives ◽  
Dialkyl Acetylenedicarboxylates ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields ◽  
Neutral Conditions

A new and efficient one-pot synthesis of polysubstituted pyrrole derivatives by three-component reaction between dialkyl acetylenedicarboxylates, triphenylphosphine, 2-aminopyridin derivatives in the presence of arylglyoxals is described. The reactions were performed in dichloromethane at room temperature and neutral conditions and afforded high yields of products.

Synthesis of 4-arylethyl-6-arylpyrimidine-2-thiols through aza-Michael addition/nucleophilic addition/aromatization tandem reactions

2018 ◽  
Vol 24 (1) ◽  
pp. 23-26
Author(s):  
Zheng Li ◽  
Wenli Song ◽  
Jiaojiao He ◽  
Yan Du ◽  
Jingya Yang
Keyword(s):  
Efficient Method ◽  
Michael Addition ◽  
Nucleophilic Addition ◽  
Tandem Reactions ◽  
Reaction Conditions ◽  
High Yields ◽  
Work Up

Abstract An efficient method for the synthesis of the title compounds by reactions of divinyl ketones with thiourea is described. This protocol has the advantages of high yields, mild reaction conditions and simple work-up procedure.

A bromine-radical mediated three-component reaction comprising allenes, electron-deficient alkenes and allyl bromides: facile synthesis of 2-bromo-1,7-dienes

2014 ◽  
Vol 50 (45) ◽  
pp. 5993-5996 ◽  
Author(s):  
Takashi Kippo ◽  
Ilhyong Ryu
Keyword(s):  
Coupling Reaction ◽  
Facile Synthesis ◽  
Three Component Reaction ◽  
High Yields ◽  
Three Component Coupling

A bromine-radical mediated three-component coupling reaction was effectively achieved by the use of allenes, electron-deficient alkenes, and allyl bromides and led to the synthesis of 2-bromo-1,7-dienes in good to high yields.

scholarly journals Enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes catalyzed by binaphthyl-derived organocatalysts

2012 ◽  
Vol 8 ◽  
pp. 699-704 ◽  
Author(s):  
Saet Byeol Woo ◽  
Dae Young Kim
Keyword(s):  
Michael Addition ◽  
Catalyst Loading ◽  
High Yields ◽  
Low Catalyst Loading

The highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes, promoted by binaphthyl-modified chiral bifunctional organocatalysts is described. This reaction afforded the chiral functionalized naphthoquinones in high yields (81–95%) and excellent enantioselectivities (91–98% ee) under low catalyst loading (1 mol %).

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