5-Nitro-2-furoyl chloride

Solvolysis rate constants of 5-nitro-2-furoyl chloride in 27 different solvents were well correlated with the extended Grunwald-Winstein equation, with sensitivity values of 1.20 0.05 and 0.37 0.02 for I and m, respectively. These data, the range of values found for A// and AS, and the solvent kinetic isotope effect (SKIE, MeOH MeOD) of 2.65 were in accord with an 5 2 mechanism. ... 

A soln. of cinnamaldehyde thiosemicarbazone in dry tetrahydrofuran stirred at room temp, with 1.4 equivalents of NaHCOg, a soln. of an equimolar quantity of 5-nitro-2-furoyl chloride in the same solvent added, stirred 2 hrs., and refluxed 30 min. cinnamaldehyde S-(5-nitro-2-furoyl)thiosemicarbazone. Y 87%. F. e. s. W. S. Sherman and A. A. Alter, J. Org. Chem. 21, 2237 (1962). 

Acylation of the common starting 3,4-diaminonitrobenzene with furoyl chloride proceeds on the more basic amino group meta to the nitro group to give 140. This is then cyclized to imidazole 141 by means of acetic anhydride. Reduction of the nitro group (142), followed by condensation with ethyl acetoacetate affords furodazole (143) [26]. 

A soln. of 5-nitrofuran-2-carboxylic acid chloride in dioxane added dropwise to an ice-cooled suspension of an equimolar amount of 4-hydroxy-4-methyl-3-thio-semicarbazide and NaHCOg in dioxane containing some water with stirring, whidi is continued 3 hrs. at room temp. l-(5-nitro-2-furoyl)-4-hydroxy-4-methyl-3-thiosemicarbazide. Y 82%. F. e. and ring closure of the products s. E. Muller and P. Grobner, M. 106, 27 (1975). 

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See also in sourсe #XX -- [ ]

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