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Literature DB >> 16178565

One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling.

Mohamed S Mohamed Ahmed¹, Kei Kobayashi, Atsunori Mori.

Abstract

[reaction: see text] Four-component coupling of a terminal alkyne, hydrazine (hydroxylamine), carbon monoxide, and an aryl iodide furnishes pyrazole or isoxazole derivatives in the presence of a palladium catalyst. The reaction proceeds at room temperature and an ambient pressure of carbon monoxide in an aqueous solvent system.

Entities: Chemical

Mesh：

Substances：

Year: 2005 PMID： 16178565 DOI： 10.1021/ol051841j

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

13 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

2. TfOH mediated intermolecular electrocyclization for the synthesis of pyrazolines and its application in alkaloid synthesis.

Authors: Sesuraj Babiola Annes; Pothiappan Vairaprakash; Subburethinam Ramesh
Journal: RSC Adv Date: 2018-08-24 Impact factor: 4.036

3. Stereoselective synthesis of cis- or trans-3,5-disubstituted pyrazolidines via Pd-catalyzed carboamination reactions: use of allylic strain to control product stereochemistry through N-substituent manipulation.

Authors: Natalie C Giampietro; John P Wolfe
Journal: J Am Chem Soc Date: 2008-09-06 Impact factor: 15.419

4. Palladium-catalyzed carbonylation reactions of aryl bromides at atmospheric pressure: a general system based on Xantphos.

Authors: Joseph R Martinelli; Donald A Watson; Dominique M M Freckmann; Timothy E Barder; Stephen L Buchwald
Journal: J Org Chem Date: 2008-08-23 Impact factor: 4.354

5. Synthesis of 5-(Fluoroalkyl)isoxazole Building Blocks by Regioselective Reactions of Functionalized Halogenoximes.

Authors: Bohdan A Chalyk; Kateryna V Hrebeniuk; Yulia V Fil; Konstantin S Gavrilenko; Alexander B Rozhenko; Bohdan V Vashchenko; Oleksandr V Borysov; Angelina V Biitseva; Pavlo S Lebed; Iulia Bakanovych; Yurii S Moroz; Oleksandr O Grygorenko
Journal: J Org Chem Date: 2019-10-30 Impact factor: 4.354

10. Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives.

Authors: Zhi-Cong Geng; Jian Chen; Ning Li; Xiao-Fei Huang; Yong Zhang; Ya-Wen Zhang; Xing-Wang Wang
Journal: Beilstein J Org Chem Date: 2012-10-09 Impact factor: 2.883

One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling.

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

2. TfOH mediated intermolecular electrocyclization for the synthesis of pyrazolines and its application in alkaloid synthesis.

3. Stereoselective synthesis of cis- or trans-3,5-disubstituted pyrazolidines via Pd-catalyzed carboamination reactions: use of allylic strain to control product stereochemistry through N-substituent manipulation.

4. Palladium-catalyzed carbonylation reactions of aryl bromides at atmospheric pressure: a general system based on Xantphos.

5. Synthesis of 5-(Fluoroalkyl)isoxazole Building Blocks by Regioselective Reactions of Functionalized Halogenoximes.

6. Amines as key building blocks in Pd-assisted multicomponent processes.

Review 7. Pyrazoles as potential anti-angiogenesis agents: a contemporary overview.

8. Metal-free synthesis of ynones from acyl chlorides and potassium alkynyltrifluoroborate salts.

9. 3-tert-Butyl-1-(3-nitro-phen-yl)-1H-pyrazol-5-amine.

10. Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives.