A Three-Component Catalyst-Free Approach to Regioselective Synthesis of Dual Highly Functionalized Fused Pyrrole Derivatives in Water–Ethanol Media: Thermodynamics versus Kinetics

2014 ◽  
Vol 2 (5) ◽  
pp. 1155-1163 ◽  
Author(s):  
Xue-Bing Chen ◽  
Zhi-Cheng Liu ◽  
Li-Fen Yang ◽  
Sheng-Jiao Yan ◽  
Jun Lin
Keyword(s):  
Regioselective Synthesis ◽  
Pyrrole Derivatives ◽  
Catalyst Free

ChemInform Abstract: Catalyst-Free Three-Component Domino Reactions for Regioselective Synthesis of Multi-Functional Fused Pyrroles.

ChemInform ◽  
2015 ◽  
Vol 46 (41) ◽  
pp. no-no
Author(s):  
Xue-Bing Chen ◽  
Sheng-Jiao Yan ◽  
An Su ◽  
Wei Liu ◽  
Jun Lin
Keyword(s):  
Regioselective Synthesis ◽  
Domino Reactions ◽  
Catalyst Free

Catalyst-free three-component domino reactions for regioselective synthesis of multi-functional fused pyrroles

Tetrahedron ◽  
2015 ◽  
Vol 71 (29) ◽  
pp. 4745-4751 ◽  
Author(s):  
Xue-Bing Chen ◽  
Sheng-Jiao Yan ◽  
An Su ◽  
Wei Liu ◽  
Jun Lin
Keyword(s):  
Regioselective Synthesis ◽  
Domino Reactions ◽  
Catalyst Free

Regioselective synthesis of spiro isoxazole‐oxindole‐tetrahydrothiophene hybrids via cascade reactions under catalyst‐free conditions

2019 ◽  
Vol 57 (1) ◽  
pp. 469-476 ◽  
Author(s):  
Sakkani Nagaraju ◽  
Kota Sathish ◽  
Neeli Satyanarayana ◽  
Banoth Paplal ◽  
Dhurke Kashinath
Keyword(s):  
Cascade Reactions ◽  
Regioselective Synthesis ◽  
Catalyst Free

Catalyst‐free one‐pot regioselective synthesis of benzo[ d ]imidazo[2,1‐ b ]thiazoles by heating or grinding

2019 ◽  
Vol 56 (11) ◽  
pp. 3055-3064 ◽  
Author(s):  
Kalawati Meena ◽  
Mohit Saroha ◽  
Ishani Khurana ◽  
Amita Malik ◽  
Pramod K. Rai ◽  
...  
Keyword(s):  
Regioselective Synthesis ◽  
One Pot ◽  
Catalyst Free

ChemInform Abstract: Regioselective Synthesis of Functionalized [1,8]Naphthyridine Derivatives via Three-Component Domino Reaction under Catalyst-Free Conditions.

ChemInform ◽  
2015 ◽  
Vol 46 (26) ◽  
pp. no-no
Author(s):  
Xian Feng ◽  
Jian-Jun Wang ◽  
Juan-Juan Zhang ◽  
Cheng-Pao Cao ◽  
Zhi-Bin Huang ◽  
...  
Keyword(s):  
Regioselective Synthesis ◽  
Domino Reaction ◽  
Catalyst Free

Improved Catalyst-Free Synthesis of Pyrrole Derivatives in Aqueous Media

Synlett ◽  
2013 ◽  
Vol 24 (14) ◽  
pp. 1791-1794 ◽  
Author(s):  
Fatemeh Tamaddon ◽  
Farideh Amirpoor
Keyword(s):  
Aqueous Media ◽  
Pyrrole Derivatives ◽  
Catalyst Free

Regioselective Synthesis of 2,5-Disubstituted Pyrroles via Stepwise Iododesilylation and Coupling Reactions

2018 ◽  
Vol 71 (3) ◽  
pp. 95 ◽  
Author(s):  
Qixin Yu ◽  
Xiaoyu Li ◽  
Xinyue Wang ◽  
Jianhui Liu
Keyword(s):  
Pyrrole Ring ◽  
Coupling Reaction ◽  
Regioselective Synthesis ◽  
Coupling Reactions ◽  
Pyrrole Derivatives ◽  
Final Choice ◽  
Tetrabutylammonium Fluoride ◽  
Pyrrole Nitrogen

A new protocol has been developed for the regioselective preparation of 2,5-disubstituted pyrroles. This approach is based on a stepwise iododesilylation and a subsequent coupling reaction, involving a 6-step pathway starting from the simplest pyrrole. A variety of 2,5-disubstituted pyrrole derivatives are accessible in moderate to good yields. In this study, the protection group for the pyrrole nitrogen is carefully chosen and N,N-dimethylaminosulfonyl is the final choice, which facilitates the subsequent double lithiation and makes the pyrrole moiety more stable. However, the attempted removal of this group fails under several different conditions. Instead, unexpected dimethylaminosulfonyl migration to the β-position of the pyrrole ring in the presence of tetrabutylammonium fluoride is observed.

Combinatorial synthesis of spiro[indoline-3,2′-pyrrole] derivatives via a three-component reaction under catalyst-free conditions

RSC Advances ◽  
2016 ◽  
Vol 6 (13) ◽  
pp. 10412-10418 ◽  
Author(s):  
Guanghao Shi ◽  
Xinwei He ◽  
Yongjia Shang ◽  
Meihua Xie
Keyword(s):  
Amino Acid ◽  
Combinatorial Synthesis ◽  
Pyrrole Derivatives ◽  
Catalyst Free ◽  
Three Component Reaction ◽  
Acid Esters

Reported here is a convenient catalyst-free method for preparing a series of spiro[indoline-3,2′-pyrroles] from a three-component reaction of isatins, α-amino acid and phenylpropiolic acid esters in refluxing isopropanol with high regioselectivity and yields.

Sign in / Sign up

Export Citation Format

Share Document