Catalyst-free tandem Michael addition/decarboxylation of (thio)coumarin-3-carboxylic acids with indoles: facile synthesis of indole-3-substituted 3,4-dihydro(thio)coumarins

2014 ◽  
Vol 12 (14) ◽  
pp. 2185-2188 ◽  
Author(s):  
Zhuzhou Shao ◽  
Lubin Xu ◽  
Liang Wang ◽  
Hongtao Wei ◽  
Jian Xiao
Keyword(s):  
Carboxylic Acids ◽  
Michael Addition ◽  
Facile Synthesis ◽  
Catalyst Free

The tandem Michael addition/decarboxylation of (thio)-coumarin-3-carboxylic acids with indoles gives biologically important indole-3-substituted dihydrocoumarins in good to excellent yields under catalyst-free conditions.

Catalyst free Michael addition of 3-methyl-2-pyrazolin-5-one to β-nitrostyrenes ‘on water’: a green protocol for facile synthesis of 4-(1-aryl-2-nitroethyl)-3-methyl-1H-pyrazol-5-ol

2013 ◽  
Vol 54 (45) ◽  
pp. 5941-5944 ◽  
Author(s):  
H.M. Meshram ◽  
Nandigama Satish Kumar ◽  
Jagadeesh Babu Nanubolu ◽  
L. Chandrasekhara Rao ◽  
N. Nageswara Rao
Keyword(s):  
Michael Addition ◽  
Facile Synthesis ◽  
Green Protocol ◽  
Catalyst Free

ChemInform Abstract: Catalyst Free Michael Addition of 3-Methyl-2-pyrazolin-5-one to β-Nitrostyrenes “on Water”: A Green Protocol for Facile Synthesis of 4-(1-Aryl-2-nitroethyl)-3-methyl-1H-pyrazol-5-ol.

ChemInform ◽  
2014 ◽  
Vol 45 (10) ◽  
pp. no-no
Author(s):  
H. M. Meshram ◽  
Nadigama Satish Kumar ◽  
Jagadeesh Babu Nanubolu ◽  
L. Chandrasekhara Rao ◽  
N. Nageswara Rao
Keyword(s):  
Michael Addition ◽  
Facile Synthesis ◽  
Green Protocol ◽  
Catalyst Free

Ligand-Enabled γ-C(sp3)–H Olefination of Free Carboxylic Acids

2020 ◽  
Author(s):  
Kiron Kumar Ghosh ◽  
Alexander Uttry ◽  
Francesca Ghiringhelli ◽  
Arup Mondal ◽  
Manuel van Gemmeren
Keyword(s):  
Reaction Mechanism ◽  
Carboxylic Acids ◽  
Michael Addition ◽  
Kinetic Studies ◽  
Wide Range ◽  
Palladium Catalyzed

We report the ligand enabled C(sp3)–H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.<br>

scholarly journals A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst

2020 ◽  
Vol 11 (21) ◽  
pp. 5572-5576 ◽  
Author(s):  
Noboru Hayama ◽  
Yusuke Kobayashi ◽  
Eriko Sekimoto ◽  
Anna Miyazaki ◽  
Kiyofumi Inamoto ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Tertiary Amine ◽  
Michael Addition ◽  
Arylboronic Acid ◽  
Unsaturated Carboxylic Acids

An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported.

Catalyst-Free One-Pot Synthesis of Novel Heteroarylamine Substituted Furo[3,2-c]coumarins

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1589-1592 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Mahnaz Saraei ◽  
Reyhaneh Khoeiniha
Keyword(s):  
Michael Addition ◽  
Aldol Condensation ◽  
Ring Closure ◽  
Dehydration Reaction ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Tandem Process ◽  
First Time

A high-yielding cyclocondensation of 4-hydroxycoumarin, phenylglyoxal monohydrate, and heteroarylamines proceeds without catalysis, which gives novel functionalized furo[3,2-c]coumarins and heteroarylamino alkylation of coumarin products in acetonitrile under reflux, is reported for the first time. This tandem process involves sequentially an aldol condensation, Michael addition, a ring closure, and dehydration reaction.

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