Synthesis of Dinitro-Substituted Furans, Thiophenes, and Azoles

Autor:	Anatoliy V. Vakulenko, Alan R. Katritzky, Reddy Damavarapu, Jothilingam Sivapackiam, Bogdan Draghici
Rok vydání:	2008
Předmět:	chemistry.chemical_compound Nitrate Chemistry Nitric acid Nitration Organic Chemistry Hydrazine Hydrogen peroxide Medicinal chemistry Catalysis Derivative (chemistry)
Zdroj:	Synthesis. 2008:699-706
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-2008-1032187
Popis:	Direct nitration of the corresponding mononitro furans with fuming nitric acid, thiophenes with acetyl nitrate, and thiazoles with trifluoroacetyl nitrate, gave dinitro-substituted furans, thiophenes, and thiazoles. The nitrations of 2-alkylthiophenes with 3 and 5 molar equivalents of acetyl nitrate, generated in situ, are discussed. Reactions of the mononitro furans with fuming nitric acid gave 1,1,5,5-tetrasubstituted dihydrofurans as by-products. Treatment of 5-methyl-4-nitroisoxazole with hydrazine or its methyl or phenyl derivative, followed by oxidation of the corresponding 4-amino-5-nitro-1H -pyrazoles with hydrogen peroxide (50%) gave 4,5-dinitro -1H -pyrazoles. A safe one-pot synthesis of 1-alkyl-3,5-dinitro-1H -[l,2,4]triazoles was developed from dicyandiamide.
Databáze:	OpenAIRE
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