Cut and sew: benzofuran-ring-opening enabled cyclopentenone ring formation

2020 ◽  
Vol 56 (84) ◽  
pp. 12817-12820
Author(s):  
Kai Wang ◽  
Chenghao Jiang ◽  
Zhenming Zhang ◽  
Chunyu Han ◽  
Xuewei Wang ◽  
...  
Keyword(s):  
Ring Opening ◽  
Cascade Reaction ◽  
Ring Formation ◽  
Acid Catalyzed

A broad range of fully substituted cyclopentenones are constructed efficiently via an acid catalyzed cascade reaction involving an unprecedented benzofuran-ring-opening.

Synthesis of Azocane- and Oxocane-Annulated Furans by a [2+2] Photocycloaddition–Ring-Opening Cascade

Synthesis ◽  
2020 ◽  
Author(s):  
Thorsten Bach ◽  
Xinyao Li ◽  
Christian Jandl
Keyword(s):  
Double Bond ◽  
Uv Irradiation ◽  
Alkyl Group ◽  
Ring Opening ◽  
Cascade Reaction ◽  
Coumarin Derivatives ◽  
Ring Opening Reaction ◽  
Acid Catalyzed ◽  
Subsequent Acid

AbstractThe title compounds were synthesized from readily available quinolone and coumarin derivatives by a cascade reaction (12 examples, 90–98% yield). The cascade comprised a [2+2] photocycloaddition which occurred upon sensitized irradiation at λ = 420 nm (or direct UV irradiation at λ = 366 nm) and a subsequent acid-catalyzed ring-opening reaction. A variety of substituents are compatible with the conditions and a 3-alkyl group in the coumarin (or quinolone) is crucial to achieve a high chemoselectivity. Key to the success of the ring opening is the formation of a 4,5,5a-trihydrocyclobuta-2H-furan containing a strained bridgehead double bond which stems from the allenyl group tethered to the 4-position of the starting materials.

ChemInform Abstract: Ring Formation and Ring Opening Reactions of a Dihydrothiadiazine Cycle Fused to 1,2,4-Triazole.

ChemInform ◽  
2009 ◽  
Vol 40 (13) ◽  
Author(s):  
Alexandra A. Kolodina ◽  
Alexandr V. Lesin ◽  
Yulia V. Nelyubina
Keyword(s):  
Ring Opening ◽  
Ring Formation ◽  
Ring Opening Reactions

Chemoenzymatic cascade for stilbene production from cinnamic acid catalyzed by ferulic acid decarboxylase and an artificial metathease

2019 ◽  
Vol 9 (20) ◽  
pp. 5572-5576 ◽  
Author(s):  
M. A. Stephanie Mertens ◽  
Daniel F. Sauer ◽  
Ulrich Markel ◽  
Johannes Schiffels ◽  
Jun Okuda ◽  
...  
Keyword(s):  
Ferulic Acid ◽  
Cinnamic Acid ◽  
Olefin Metathesis ◽  
Metal Contamination ◽  
Cascade Reaction ◽  
Acid Decarboxylase ◽  
Efficient Removal ◽  
Ferulic Acid Decarboxylase ◽  
Acid Catalyzed ◽  
Removal Of Metal

We report a chemoenzymatic cascade reaction for stilbene production combining decarboxylation and olefin metathesis with efficient removal of metal contamination.

Acid Catalyzed a-Pyrone Ring Formation Reactions

Heterocycles ◽  
1994 ◽  
Vol 37 (3) ◽  
pp. 1705 ◽  
Author(s):  
Okan Tarhan ◽  
Cihangir Tanyeli ◽  
Ayhan S. Demir ◽  
�demir �arslan ◽  
Idris Mecidoglu
Keyword(s):  
Ring Formation ◽  
Pyrone Ring ◽  
Acid Catalyzed

ChemInform Abstract: Lewis Acid Catalyzed Cascade Reaction to Carbazoles and Naphthalenes via Dehydrative [3 + 3]-Annulation.

ChemInform ◽  
2014 ◽  
Vol 45 (52) ◽  
pp. no-no
Author(s):  
Shaoyin Wang ◽  
Zhuo Chai ◽  
Yun Wei ◽  
Xiancui Zhu ◽  
Shuangliu Zhou ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Cascade Reaction ◽  
Acid Catalyzed
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