Cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes

2021 ◽  
Author(s):  
Lei Yang ◽  
Shun Zhou ◽  
Jian-Qiang Zhao ◽  
Yong You ◽  
Zhen-Hua Wang ◽  
...  
Keyword(s):  
Aldol Reaction ◽  
Catalyst Free ◽  
Sulfonium Ylides

The first catalyst-free cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes was developed. A series of thieno[2,3-b]indoles and benzothiophenes were smoothly obtained in high to excellent...

Diversity-Oriented Synthesis via Catalyst-Free Addition of Ketones to [e]-Fused 1H-Pyrrole-2,3-diones

Synthesis ◽  
2018 ◽  
Vol 50 (24) ◽  
pp. 4897-4904 ◽  
Author(s):  
Ekaterina Stepanova ◽  
Andrey Maslivets ◽  
Svetlana Kasatkina ◽  
Maksim Dmitriev
Keyword(s):  
Intramolecular Cyclization ◽  
Aromatic Hydrocarbons ◽  
Michael Addition ◽  
Aldol Reaction ◽  
Synthetic Approach ◽  
Reaction Conditions ◽  
Diversity Oriented Synthesis ◽  
Catalyst Free ◽  
Solvent Free Conditions ◽  
Reaction Proceeds

A facile synthetic approach towards two distinct pyrrole-based heterocyclic scaffolds has been developed by the interaction of 1H-pyrrole-2,3-diones fused at the [e]-side to a 1,4-benzoxazin-2-one or quinoxalin-2(1H)-one moiety with ketones. The described interaction proceeds either as an aldol reaction or as a Michael addition/intramolecular cyclization depending on the reaction conditions. The disclosed aldol reaction proceeds with good diastereoselectivity under catalyst-free conditions when the reaction is carried out in aromatic hydrocarbons. Products of the cascade Michael addition/intramolecular cyclization reaction are predominantly formed under catalyst-free and solvent-free conditions. The proposed strategy provides facile access to pharmaceutically interesting pyrrole-based polyheterocycles.

An efficient catalyst-free Mukaiyama-aldol reaction of fluorinated enol silyl ethers with tryptanthrin

2015 ◽  
Vol 13 (33) ◽  
pp. 8906-8911 ◽  
Author(s):  
Fu-Min Liao ◽  
Yun-Lin Liu ◽  
Jin-Sheng Yu ◽  
Feng Zhou ◽  
Jian Zhou
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Aldol Reaction ◽  
Efficient Catalyst ◽  
Silyl Ethers ◽  
Mukaiyama Aldol Reaction ◽  
Catalyst Free ◽  
Mukaiyama Aldol ◽  
Enol Silyl Ethers ◽  
Fluoroalkyl Group

We report an efficient Mukaiyama-aldol reaction of tryptanthrin with fluorinated enol silyl ethers, which is carried out in methanol without the use of any catalyst. This represents the first modification of tryptanthrin by a fluoroalkyl group, which is applied to the total synthesis of the difluoro analogues of the natural product Phaitanthrin B.

ChemInform Abstract: Catalyst-Free Aldol Reaction in a Water Medium.

ChemInform ◽  
2016 ◽  
Vol 47 (36) ◽  
Author(s):  
Weirong Yao ◽  
Yanli Cui ◽  
Peipei Wang ◽  
Yangyi Mao
Keyword(s):  
Aldol Reaction ◽  
Water Medium ◽  
Catalyst Free

Catalyst-Free Aldol Reaction in a Water Medium

2016 ◽  
Vol 13 (4) ◽  
pp. 293-296 ◽  
Author(s):  
Weirong Yao ◽  
Yanli Cui ◽  
Peipei Wang ◽  
Yangyi Mao
Keyword(s):  
Aldol Reaction ◽  
Water Medium ◽  
Catalyst Free

Catalyst-free synthesis of α1-oxindole-α-hydroxyphosphonates via phospha-aldol reaction of isatins employing N-heterocyclic phosphine (NHP)-thiourea

2016 ◽  
Vol 14 (38) ◽  
pp. 8952-8956 ◽  
Author(s):  
Nagaraju Molleti ◽  
Jun Yong Kang
Keyword(s):  
Critical Role ◽  
Aldol Reaction ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Catalyst Free ◽  
Brönsted Acid

A catalyst-free phospha-aldol reaction of isatins with NHP-thiourea has been developed and the critical role of the Brønsted acid in this transformation is unveiled.

The Role of Water in the Catalyst-Free Aldol Reaction of Water-Insoluble N -Methyl-2,4-thiazolidinedione with N -Methylisatin from QM/MM Monte Carlo Simulations

ChemPhysChem ◽  
2017 ◽  
Vol 18 (15) ◽  
pp. 2123-2131 ◽  
Author(s):  
Jianming Zhao ◽  
Fen He ◽  
Fan Zhang ◽  
Xin Yang ◽  
Zhiyue Tian ◽  
...  
Keyword(s):  
Monte Carlo ◽  
Monte Carlo Simulations ◽  
Aldol Reaction ◽  
Catalyst Free

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex

2020 ◽  
Author(s):  
José Tiago Menezes Correia ◽  
Gustavo Piva da Silva ◽  
Camila Menezes Kisukuri ◽  
Elias André ◽  
Bruno Pires ◽  
...  
Keyword(s):  
Electron Donor ◽  
Functional Group ◽  
Photoexcited Electron ◽  
One Pot ◽  
Quaternary Centers ◽  
Metal Free ◽  
Acceptor Complex ◽  
Catalyst Free ◽  
Donor Acceptor ◽  
Radical Cascade

A metal- and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donor-aceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. <a>The method provides an operationally simple, robust and step-economical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential one-pot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches</a>.

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