Literature DB >> 18831568

Et3N-induced demethylation-annulation of 3-alkynyl-4-methoxy-2-pyridones and structurally related compounds in the synthesis of furan-fused heterocycles.

David Conreaux1, Sébastien Belot, Philippe Desbordes, Nuno Monteiro, Geneviève Balme.   

Abstract

Various 3-iodo-4-methoxypyridin-2-ones and related pyrone and coumarin derivatives have been demonstrated as readily available precursors of 2-substituted furan-fused heterocycles by means of in situ sequential Sonogashira-acetylide coupling, dealkylation, and regioselective furan annulation reactions. A Et3N-induced S(N)2 process has been established that accounts for the dealkylation process.

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Year:  2008        PMID： 18831568     DOI： 10.1021/jo8014038

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

Review 1.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

Review 2.  Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.

Authors:  Imtiaz Khan; Aliya Ibrar; Sumera Zaib
Journal:  Top Curr Chem (Cham)       Date:  2021-01-05

3.  Expeditious entry to novel 2-methylene-2,3-dihydrofuro[3,2-c] chromen-2-ones from 6-chloro-4-hydroxychromen-2-one and propargylic alcohols.

Authors:  Noel Nebra; Alba E Díaz-Álvarez; Josefina Díez; Victorio Cadierno
Journal:  Molecules       Date:  2011-08-02       Impact factor: 4.411

Review 4.  Synthetic Routes to Coumarin(Benzopyrone)-Fused Five-Membered Aromatic Heterocycles Built on the α-Pyrone Moiety. Part 1: Five-Membered Aromatic Rings with One Heteroatom.

Authors:  Eslam Reda El-Sawy; Ahmed Bakr Abdelwahab; Gilbert Kirsch
Journal:  Molecules       Date:  2021-01-18       Impact factor: 4.411

Review 5.  Furo[3,2-c]coumarins carrying carbon substituents at C-2 and/or C-3. Isolation, biological activity, synthesis and reaction mechanisms.

Authors:  Iván Cortés; L Javier Cala; Andrea B J Bracca; Teodoro S Kaufman
Journal:  RSC Adv       Date:  2020-09-10       Impact factor: 4.036

6.  Rhodium(i)-catalyzed C6-selective C-H alkenylation and polyenylation of 2-pyridones with alkenyl and conjugated polyenyl carboxylic acids.

Authors:  Haoqiang Zhao; Xin Xu; Zhenli Luo; Lei Cao; Bohan Li; Huanrong Li; Lijin Xu; Qinghua Fan; Patrick J Walsh
Journal:  Chem Sci       Date:  2019-09-09       Impact factor: 9.825
  6 in total

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