Chemoselective acid-catalyzed [4 + 2]-cycloaddition reactions of ortho-quinone methides and styrenes/stilbenes/cinnamates

2020 ◽  
Vol 18 (43) ◽  
pp. 8854-8866
Author(s):  
Kornkamon Akkarasereenon ◽  
Kassrin Tangdenpaisal ◽  
Somsak Ruchirawat ◽  
Poonsakdi Ploypradith
Keyword(s):  
Cycloaddition Reactions ◽  
Quinone Methides ◽  
Acid Catalyzed

Chemoselective [4 + 2]-cycloaddition reactions between o-QMs and different olefins—styrenes, stilbenes, and cinnamates—yielded distinct cycloadducts in moderate to good yields.

A New Cycloaddition Profile for ortho-Quinone Methides: Photoredox-Catalyzed [6+4] Cycloadditions for Synthesis of Benzo[b]cyclopenta[e]oxepines

2022 ◽  
Author(s):  
Kenta Tanaka ◽  
Yosuke Asada ◽  
Yujiro Hoshino
Keyword(s):  
Visible Light ◽  
Cycloaddition Reactions ◽  
Quinone Methides

Visible-light-induced [6+4] cycloaddition reactions of ortho-quinone methides have been developed. The reaction of ortho-quinone methides with pentafulvenes in the presence of a thioxanthylium photoredox catalyst afforded benzo[b]cyclopenta[e]oxepines. The present reaction...

Efficient Synthesis of Chromenes from Vinyl o-Quinone Methides via a Brønsted Acid Catalyzed Electrocyclization Process

Synthesis ◽  
2018 ◽  
Vol 50 (12) ◽  
pp. 2416-2422 ◽  
Author(s):  
Man-Su Tu ◽  
Guang-Jian Mei ◽  
Feng Shi ◽  
Si-Jia Liu ◽  
Xiao-Li Jiang ◽  
...  
Keyword(s):  
Efficient Method ◽  
Research Area ◽  
Environmentally Benign ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Efficient Synthesis ◽  
Quinone Methides ◽  
Efficient Approach ◽  
Brönsted Acid ◽  
Acid Catalyzed

An efficient approach for the synthesis of chromene derivatives from vinyl o-quinone methides was established via a Brønsted acid catalyzed electrocyclization. By using this methodology, a series of structurally diversified chromenes was synthesized in a highly atom-economic and environmentally benign manner with generally good to excellent yields (up to 98% yield). This reaction will not only provide an efficient method for the construction of chromene scaffolds, but also enrich the research area of o-quinone methides.

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.

Synthesis of bicyclic vinyl triazenes by Ficini-type reactions

2021 ◽  
Author(s):  
Carl Thomas Bormann ◽  
Farzaneh Fadaei-Tirani ◽  
Rosario Scopelliti ◽  
Kay Severin
Keyword(s):  
Lewis Acid ◽  
Cycloaddition Reactions ◽  
Acid Catalyzed

Cyclobutenyl triazenes are obtained by Lewis acid-catalyzed [2 + 2] cycloaddition reactions of 1-alkynyl triazenes and enones. The triazene group in the product enables rearrangements and functionalizations.

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