Diastereoselective Synthesis of Tetrahydroquinolines Bearing Oxindole Scaffolds via Annulation of in Situ Generated p ‐Quinone Methides

2020 ◽  
Vol 362 (13) ◽  
pp. 2755-2759 ◽  
Author(s):  
Junwei Wang ◽  
Lei Zhao ◽  
Lin Zhao ◽  
Xiang Pan ◽  
Cheng Lv ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Quinone Methides

Diastereoselective Synthesis of Tetrahydroquinolines via [4 + 2] Annulation between in Situ Generated p-Quinone Methides and Nitroalkenes

2018 ◽  
Vol 20 (19) ◽  
pp. 5995-5998 ◽  
Author(s):  
Junwei Wang ◽  
Xiang Pan ◽  
Jian Liu ◽  
Lin Zhao ◽  
Ying Zhi ◽  
...  
Keyword(s):  
Diastereoselective Synthesis ◽  
Quinone Methides

scholarly journals Diastereoselective synthesis of CF3-dihydrobenzofurans by [4+1] annulation of in situ-generated CF3-o-quinone methides and sulfur ylides

RSC Advances ◽  
2020 ◽  
Vol 10 (63) ◽  
pp. 38588-38591
Author(s):  
Babli K. Jha ◽  
Jaggaraju Prudhviraj ◽  
Prathama S. Mainkar ◽  
Nagender Punna ◽  
Srivari Chandrasekhar
Keyword(s):  
Diastereoselective Synthesis ◽  
Quinone Methides ◽  
Reaction Conditions ◽  
Sulfur Ylides

The first [4 + 1] annulation reaction of in situ-generated highly electrophilic CF3-ortho-quinone methides with sulphur ylides has been put forth under mild reaction conditions to access CF3-dihydrobenzofurans.

scholarly journals Highly Diastereoselective Synthesis of Tetrahydroquinoline Derivatives via [4 + 2] Annulation of Ortho-Tosylaminophenyl-Substituted Para-Quinone Methides and Cyanoalkenes

2021 ◽  
Vol 9 ◽  
Author(s):  
Taiwei Dong ◽  
Peifeng Wei ◽  
Min Li ◽  
Feng Gao ◽  
Yuan Qin
Keyword(s):  
Biologically Active ◽  
Structural Motif ◽  
Diastereoselective Synthesis ◽  
Atom Economy ◽  
Quinone Methides ◽  
One Pot ◽  
Reaction Performance ◽  
High Yields ◽  
Active Natural

As a privileged structural motif, tetrahydroquinoline skeletons widely exist in biologically active natural products and pharmaceuticals. In this protocol, a highly diastereoselective [4 + 2] annulation of ortho-tosylaminophenyl-substituted p-QMs and cyanoalkenes to construct tetrahydroquinoline derivatives has been successfully achieved. This strategy proceeds efficiently under mild condition, offering straightforward route to a variety of 4-aryl-substituted tetrahydroquinolines with high yields, excellent diastereoselectivities, broad functional group tolerance as well as gram-scale capacity. Moreover, a one-pot reaction sequence utilizing in situ generated p-QMs under the similar condition to build tetrahydroquinoline framework is smoothly conducted with good reaction performance as well as step and atom economy.

Lewis acid-catalyzed tandem cyclization of in situ generated o-quinone methides and arylsulfonyl hydrazides for a one-pot entry to 3-sulfonylbenzofurans

2019 ◽  
Vol 6 (24) ◽  
pp. 3929-3933 ◽  
Author(s):  
Fan-Xiao Meng ◽  
Ruo-Nan Wang ◽  
Hong-Li Huang ◽  
Shu-Wen Gong ◽  
Qian-Li Li ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Quinone Methides ◽  
One Pot ◽  
Acid Catalyzed ◽  
Tandem Cyclization ◽  
First Time

Lewis acid-mediated one-pot tandem cyclization of o-QMs with arylsulfonyl hydrazides was described for the first time and the corresponding 3-sulfonylbenzofuran products were obtained in moderate to good yields.

scholarly journals Asymmetric Synthesis of 2,3-Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o -Quinone Methides

2017 ◽  
Vol 23 (21) ◽  
pp. 5137-5142 ◽  
Author(s):  
Nicole Meisinger ◽  
Lukas Roiser ◽  
Uwe Monkowius ◽  
Markus Himmelsbach ◽  
Raphaël Robiette ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Quinone Methides

scholarly journals Correction: An organic-base catalyzed asymmetric 1,4-addition of tritylthiol to in situ generated aza-o-quinone methides at the H2O/DCM interface

2019 ◽  
Vol 55 (64) ◽  
pp. 9567-9567
Author(s):  
Xianghui Liu ◽  
Kai Wang ◽  
Wengang Guo ◽  
Yan Liu ◽  
Can Li
Keyword(s):  
Organic Base ◽  
Quinone Methides

Correction for ‘An organic-base catalyzed asymmetric 1,4-addition of tritylthiol to in situ generated aza-o-quinone methides at the H2O/DCM interface’ by Xianghui Liu et al., Chem. Commun., 2019, 55, 2668–2671.

Synthesis of 4-styrylcoumarins via FeCl3-promoted cascade reactions of propargylamines with β-keto esters

2019 ◽  
Vol 17 (16) ◽  
pp. 4005-4013 ◽  
Author(s):  
Li-Qin Yan ◽  
Xiaoting Cai ◽  
Xinwei He ◽  
Hui Wang ◽  
Mengqing Xie ◽  
...  
Keyword(s):  
Cascade Reactions ◽  
Cyclization Reaction ◽  
Quinone Methides ◽  
Keto Esters ◽  
Tandem Cyclization

A versatile and highly regioselective FeCl3-promoted tandem cyclization reaction of in situ generated alkynyl o-quinone methides (o-AQMs) with β-keto esters has been developed.

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