Synthesis of N -Acyl- N ′-Sulfonyl Hydrazides from Sulfonyl Hydrazides and Activated Amides.

A methodology was developed for synthesizing N -acyl- N '-sulfonyl hydrazides through acyl substitution reactions between activated amides and arylsulfonyl hydrazides. Optimization of the reaction conditions revealed that using Cs₂CO₃ as a base and 1,4-dioxane as a solvent at 25 °C for 12 hours produced the highest yields. Among various amides tested, N -benzoylsuccinimide was found to be the most reactive, with reduced reactivity observed for N -mesityl-, N -tosyl-, and N -Boc-substituted tertiary benzoyl amides. Cross-reactions between a diverse range of N -benzoylsuccinimides and arylsulfonyl hydrazides successfully produced the corresponding N -acyl- N′ -sulfonyl hydrazides with yields ranging from 63% to 94%. [ABSTRACT FROM AUTHOR]