METHOD OF PRODUCING TETRASUBSTITUTED 4-DIAZO-5,5-DIALKYL-2,2-DIARYLDIHYDROFURAN-3(2H)-ONES Russian patent published in 2015 - IPC C07D307/58 C07D307/66 

FIELD: chemistry.

SUBSTANCE: invention relates to an efficient and ecologically clean method of producing 4-diazo-5,5-dialkyl-2,2-diaryldihydrofuran-3(2H)-ones of formula 1 , where Alk, Alk' = Me, Et, cycloalkyl or other alkyl groups, and Ar, Ar' = Ph, p-MeO-C6H4, p-F-C6H4, p-Cl-C6H4 and other substituted or unsubstituted aryl groups, via a multistep process from 1,1-dialkylprop-2-yn-1-ols and benzophenones, wherein the introduction of a diazo-function into the molecular structure is carried out by nitrating 2,2-dialkyl-5,5-diaryldihydrofuran-3(2H)-ones with sodium nitrite in an aqueous-organic solution of hydrochloric acid, condensing the formed 2,2-dialkyl-5,5-diarylfuran-3,4(2H,5H)-diones with p-toluenesulphonyl hydrazide and converting tosylhydrazones into target 4-diazo-5,5-dialkyl-2,2-diaryldihydrofuran-3(2H)-ones in an aqueous alkaline solution with output of up to 97% at the final step of said ecologically clean process and total output of up to 37%.

EFFECT: method avoids the use of environmentally hazardous substances at all steps; the obtained compounds can be used as precursors in the synthesis of biologically active and medicinal preparations.

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