Mannich-Type Reaction for Synthesis of 3-Methyl-4-nitroimino-tetrahydro-1,3,5-oxadiazine

Abstract

The reaction of N-methyl-N′-nitroguanidine with 3-methyl-4-nitroimino-tetrahydro-1,3,5-oxadiazine is a Mannich-type reaction. The reaction was catalyzed by several organic and inorganic bases at different reaction times and temperatures. Three inorganic base catalysts [potassium carbonate (K₂CO₃), sodium hydrogen carbonate (NaHCO₃), and sodium hydroxide (NaOH)] and several organic bases (methylamine, ethamine, iso-propylamine, and n-butylamine) have been studied. The results showed that both the inorganic and organic base catalysts can be used as catalysts, with the organic bases performing better. N-Methyl-N′-nitroguanidine reacts to give the title compound 2 and is catalyzed by both acids and bases. The intensity of inorganic base catalysts, reaction temperature, and reaction time had significant effects on the products.

GRAPHICAL ABSTRACT

Keywords:

• Formaldehyde
• Mannich reaction
• 3-methyl-4-nitroimino-tetrahydro-1,3,5-oxadiazine
• N-(1,5-dimethyl-1,3,5-triazinan-2-ylidene)nitramide
• N-(5-ethyl-1-methyl-1,3,5-triazinan-2-ylidene)nitramide
• N-methyl-N′-nitroguanidine

ACKNOWLEDGMENT

We are grateful to the “Nonprofit Industry-Specific (Agriculture)” Technology Support Project of China (No. 200903054) for financial support.

Notes

^a Both compounds 3a and 2 were detected.

^b Only compound 3a was detected.

^a Both compounds 3a and 2 were detected.

^b Only compound 3a was detected.

^a Yield of isolated compound 3a.

^b Yield of isolated compound 2.

^c Yield of isolated compound 3.