October 13, 2024, 08:29:15 AM
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Topic: carbohydrazide derivatives  (Read 1053 times)

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Offline NATO

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carbohydrazide derivatives
« on: September 25, 2024, 12:57:47 PM »
I do know that semicarbazide(aminourea) react with formic acid to form 1,2,4-triazol-3-one (1:1 molar ratio). Will carbohydrazide (diaminourea) react the same way to form amino-triazolone? Could tetrazinone be formed instead of amino-triazolone ?

Carbohydrazide cyclocondensate with aldehydes to form tetrazines



Will Carbohydrazide react with formaldehyde to form 1,2,4,5-tetrazine-3-one ?

Offline rolnor

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Re: carbohydrazide derivatives
« Reply #1 on: September 26, 2024, 03:27:19 AM »
Two nitrogens on the same sp3 carbon is not very stable, its like an aminal. I dont think this will happen spontaneously, maybe you can force this somehow.

Offline NATO

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Re: carbohydrazide derivatives
« Reply #2 on: September 28, 2024, 06:32:15 AM »
After searching it a bit, amiNes like to react with C=O bonds, forming -N=C- +H2O while amiDes react with -OH bonds forming -NH-C- +H2O. So CHZ with formic acid will for sure react with the amine forming O=C-(NH-NH2)-(NH-N=CH-OH). Now the -OH group will not react with the second amiNe group (-NH3). If it will, it will react with the amiDe (-NH-) group closing the ring, forming amino-triazol-one. Now the point is, how reactive the -NH group going to be with the -OH group ? In the case of semicarbazide, the amiDe group is a primary amiDe, easily reacting with the -OH group forming -NH-C- and clozing the ring, but in the case of CHZ, one H is replaced with the amiNe group, making the amiDe less reactive right ?

Offline rolnor

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Re: carbohydrazide derivatives
« Reply #3 on: September 29, 2024, 03:29:33 AM »

I am not sure that I follow, the molecule you have as product is not stable I think, not on silica-tlc, and I doubt it will form at all, you could search Reaxsys or Casreact and see if you can make these compounds

Offline NATO

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Re: carbohydrazide derivatives
« Reply #4 on: October 01, 2024, 05:15:21 AM »
How Reaxsys or Casreact works ? I could not figured out.

Offline rolnor

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