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Literature DB >> 14870847

A study of the synthesis of triazoles using microwave irradiation.

Kenneth A Savin¹, Michael Robertson, Doug Gernert, Steven Green, Erik J Hembre, Jessie Bishop.

Abstract

Herein we describe the conversion of a known [3+2] cycloaddition reaction between an azide and an acetylene from a thermally promoted reaction to a microwave assisted process. Modification of conditions including concentration, temperature, solvent type and time were investigated. This methodology study led us to use high concentration and high temperatures to achieve the desired fast reaction times and high yields.

Entities: Chemical

Mesh：

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Year: 2003 PMID： 14870847 DOI： 10.1023/b:modi.0000006801.27748.3b

Source DB: PubMed Journal: Mol Divers ISSN： 1381-1991 Impact factor: 2.943

5 in total

Review 1. Biotransformation reactions of five-membered aromatic heterocyclic rings.

Authors: Deepak K Dalvie; Amit S Kalgutkar; S Cyrus Khojasteh-Bakht; R Scott Obach; John P O'Donnell
Journal: Chem Res Toxicol Date: 2002-03 Impact factor: 3.739

2. Synthesis of C-carbamoyl-1,2,3-triazoles by microwave-induced 1,3-dipolar cycloaddition of organic azides to acetylenic amides.

Authors: Alan R Katritzky; Sandeep K Singh
Journal: J Org Chem Date: 2002-12-13 Impact factor: 4.354

3. Synthesis and pharmacological evaluation of CNS activities of [1,2,3]triazolo[4,5-b][1,5]-, imidazolo[4,5-b][1,5]-, and pyrido[2,3-b][1,5]benzodiazepines. 10-Piperazinyl-4H-1,2,3-triazolo[4,5-b][1,5]benzodiazepines with neuroleptic activity.

Authors: J K Chakrabarti; T M Hotten; I A Pullar; D J Steggles
Journal: J Med Chem Date: 1989-10 Impact factor: 7.446

4. Bioisosteres of arecoline: 1,2,3,6-tetrahydro-5-pyridyl-substituted and 3-piperidyl-substituted derivatives of tetrazoles and 1,2,3-triazoles. Synthesis and muscarinic activity.

Authors: E K Moltzen; H Pedersen; K P Bøgesø; E Meier; K Frederiksen; C Sánchez; H Løve Lembøl
Journal: J Med Chem Date: 1994-11-25 Impact factor: 7.446

5. Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy) [1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-ones with combined H1-antihistamine and mast cell stabilizing properties.

Authors: D R Buckle; C J Rockell; H Smith; B A Spicer
Journal: J Med Chem Date: 1986-11 Impact factor: 7.446

5 in total

3 in total

A study of the synthesis of triazoles using microwave irradiation.

Review 1. Biotransformation reactions of five-membered aromatic heterocyclic rings.

2. Synthesis of C-carbamoyl-1,2,3-triazoles by microwave-induced 1,3-dipolar cycloaddition of organic azides to acetylenic amides.

3. Synthesis and pharmacological evaluation of CNS activities of [1,2,3]triazolo[4,5-b][1,5]-, imidazolo[4,5-b][1,5]-, and pyrido[2,3-b][1,5]benzodiazepines. 10-Piperazinyl-4H-1,2,3-triazolo[4,5-b][1,5]benzodiazepines with neuroleptic activity.

4. Bioisosteres of arecoline: 1,2,3,6-tetrahydro-5-pyridyl-substituted and 3-piperidyl-substituted derivatives of tetrazoles and 1,2,3-triazoles. Synthesis and muscarinic activity.

5. Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy) [1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-ones with combined H1-antihistamine and mast cell stabilizing properties.

1. In situ generation and intramolecular Schmidt reaction of keto azides in a microwave-assisted flow format.

2. One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor.

3. Dimerization of propargyl and homopropargyl 6-azido-6-deoxy-glycosides upon 1,3-dipolar cycloaddition.