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Literature DB >> 20815385

Cyano Diels-Alder and cyano ene reactions. Applications in a formal [2 + 2 + 2] cycloaddition strategy for the synthesis of pyridines.

Abstract

Two metal-free, formal [2 + 2 + 2] cycloaddition strategies for the construction of polycyclic pyridine derivatives are described that proceed via pericyclic cascade mechanisms featuring the participation of unactivated cyano groups as enophile and dienophile cycloaddition partners.

Entities: Chemical Species

Mesh：

Substances：
Cyanides
Pyridines

Year: 2010 PMID： 20815385 PMCID： PMC2944912 DOI： 10.1021/ja106901u

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

10 in total

1. Construction of pyridine rings by metal-mediated [2 + 2 + 2] cycloaddition.

Authors: Jesús A Varela; Carlos Saá
Journal: Chem Rev Date: 2003-09 Impact factor: 60.622

2. Formal [2 + 2 + 2] cycloaddition strategy based on an intramolecular propargylic ene reaction/Diels-Alder cycloaddition cascade.

Authors: Julia M Robinson; Takeo Sakai; Katsuhiko Okano; Takafumi Kitawaki; Rick L Danheiser
Journal: J Am Chem Soc Date: 2010-08-18 Impact factor: 15.419

Review 3. gem-disubstituent effect: theoretical basis and synthetic applications.

Authors: Michael E Jung; Grazia Piizzi
Journal: Chem Rev Date: 2005-05 Impact factor: 60.622

4. Ene reactions between two alkynes? Doors open to thermally induced cycloisomerization of macrocyclic triynes and enediynes.

Authors: Iván González; Anna Pla-Quintana; Anna Roglans; Anna Dachs; Miquel Solà; Teodor Parella; Jordi Farjas; Pere Roura; Vega Lloveras; José Vidal-Gancedo
Journal: Chem Commun (Camb) Date: 2010-03-09 Impact factor: 6.222

5. Intramolecular ene reaction of 1,6-fullerenynes: a new synthesis of allenes.

Authors: Margarita Altable; Salvatore Filippone; Angel Martín-Domenech; Mireia Güell; Miquel Solà; Nazario Martín
Journal: Org Lett Date: 2006-12-21 Impact factor: 6.005

6. The fascinating construction of pyridine ring systems by transition metal-catalysed [2 + 2 + 2] cycloaddition reactions.

Authors: Barbara Heller; Marko Hapke
Journal: Chem Soc Rev Date: 2007-05-02 Impact factor: 54.564

7. 1-Azadienes in cycloaddition and multicomponent reactions towards N-heterocycles.

Authors: Bas Groenendaal; Eelco Ruijter; Romano V A Orru
Journal: Chem Commun (Camb) Date: 2008-09-08 Impact factor: 6.222

8. Ene reaction of arynes with alkynes.

Authors: Thiruvellore Thatai Jayanth; Masilamani Jeganmohan; Mu-Jeng Cheng; San-Yan Chu; Chien-Hong Cheng
Journal: J Am Chem Soc Date: 2006-02-22 Impact factor: 15.419

9. 2-azabicyclo[2.2.2]octa-3,5-dione via a nitrile Diels-Alder reaction.

Authors: Cynthia K McClure; Jeffrey S Link
Journal: J Org Chem Date: 2003-10-17 Impact factor: 4.354

10. Hetero-Diels-Alder reaction of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with arylsulfonylcyanides. Synthesis and antimicrobial activity of 4-hydroxy-2-(arylsulfonyl)pyridines.

Authors: Ibrar Hussain; Mirza Arfan Yawer; Michael Lalk; Ulrike Lindequist; Alexander Villinger; Christine Fischer; Peter Langer
Journal: Bioorg Med Chem Date: 2008-10-17 Impact factor: 3.641

10 in total

7 in total

1. Why nature eschews the concerted [2 + 2 + 2] cycloaddition of a nonconjugated cyanodiyne. Computational study of a pyridine synthesis involving an ene-Diels-Alder-bimolecular hydrogen-transfer mechanism.

Authors: Yu Lan; Rick L Danheiser; K N Houk
Journal: J Org Chem Date: 2012-01-25 Impact factor: 4.354

2. Nickel-catalyzed cyclizations of enoates and chiral allenes: an approach to domoic acid.

Authors: Ahmad S ElDouhaibi; Refaie M Kassab; Minsoo Song; John Montgomery
Journal: Chemistry Date: 2011-04-27 Impact factor: 5.236

3. Expanding the Chemical Space of Tetracyanobuta-1,3-diene (TCBD) through a Cyano-Diels-Alder Reaction: Synthesis, Structure, and Physicochemical Properties of an Anthryl-fused-TCBD Derivative.

Authors: Luis M Mateo; Luca Sagresti; Yusen Luo; Dirk M Guldi; Tomas Torres; Giuseppe Brancato; Giovanni Bottari
Journal: Chemistry Date: 2021-10-12 Impact factor: 5.020