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Literature DB >> 16594694

Synthesis of substituted pyridine derivatives via the ruthenium-catalyzed cycloisomerization of 3-azadienynes.

Abstract

We describe a two-step conversion of various N-vinyl and N-aryl amides to the corresponding substituted pyridines and quinolines, respectively. The process involves the direct conversion of amides, including sensitive N-vinyl amides, to the corresponding trimethylsilyl alkynyl imines followed by a ruthenium-catalyzed protodesilylation and cycloisomerization. A wide range of new alkynyl imines are prepared and readily converted to the corresponding azaheterocycles.

Entities: Chemical

Year: 2006 PMID： 16594694 DOI： 10.1021/ja060626a

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

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Cited

29 in total

1. Synthesis of dihydropyridines and pyridines from imines and alkynes via C-H activation.

Authors: Denise A Colby; Robert G Bergman; Jonathan A Ellman
Journal: J Am Chem Soc Date: 2008-02-27 Impact factor: 15.419

Review 2. 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

3. Pyridine synthesis from oximes and alkynes via rhodium(III) catalysis: Cp* and Cp(t) provide complementary selectivity.

Authors: Todd K Hyster; Tomislav Rovis
Journal: Chem Commun (Camb) Date: 2011-10-10 Impact factor: 6.222

4. 2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

Authors: Kangnan Li; Xinxin Shao; Luke Tseng; Steven J Malcolmson
Journal: J Am Chem Soc Date: 2018-01-04 Impact factor: 15.419

Synthesis of substituted pyridine derivatives via the ruthenium-catalyzed cycloisomerization of 3-azadienynes.

1. Synthesis of dihydropyridines and pyridines from imines and alkynes via C-H activation.

Review 2. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

3. Pyridine synthesis from oximes and alkynes via rhodium(III) catalysis: Cp* and Cp(t) provide complementary selectivity.

4. 2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.

5. Three-component coupling sequence for the regiospecific synthesis of substituted pyridines.

6. 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.

7. Rh(III)-catalyzed regioselective synthesis of pyridines from alkenes and α,β-unsaturated oxime esters.

8. One-pot synthesis of highly functionalized pyridines via a rhodium carbenoid induced ring expansion of isoxazoles.

9. Synthesis of pyridines from ketoximes and terminal alkynes via C-H bond functionalization.

10. Ruthenium-catalyzed cycloisomerization-6pi-cyclization: a novel route to pyridines.