Process for preparing 1-amino-1,2,3-triazole

Details Process for preparing 1-amino-1,2,3-triazole Process for preparing 1-amino-1,2,3-triazole

1996-04-30

1998-03-17

Morris, Patricia L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D24904

Patent

active

057288410

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to a novel process for preparing 1-amino-1,2,3-triazole which is an intermediate for producing 1,2,3-triazole, a starting material for antibiotics useful as drug.


BACKGROUND ART

Several processes for preparing N-amino-1,2,3-triazole derivatives have hitherto been known (see Adv. in Heterocycl. Chem., Vol. 53, p. 113 (1992)).
These conventional techniques have their several disadvantages and are not necessarily satisfactory when applied to industrial production. For example, a process starting with 1,2,3-triazole has such problems that 1,2,3-triazole itself is expensive, and the positional selectivity of 1- or 2-amination and chemical yield in the amination are low (see Zh. Org. Khim., Vol. 28, p. 1320 (1992) and Japanese Patent Publication (unexamined) No. Hei 5-502884 (International Patent Publication No. WO 92/00981)). A process starting with glyoxal bisbenzoyl-hydrazone requires two steps, and the chemical yield reached is as extremely low as not higher than 10%. Moreover, the working efficiency of the process, when applied to mass production of N-amino-1,2,3-triazole from the glyoxal bisbenzoylhydrazone, is inordinately poor (see Ber. d. D. Chem. Gesellschaft, Vol. 42, p. 659 (1909)).
Processes for preparing a 1-amino-1,2,3-triazole derivative represented by formula (V): ##STR3## wherein R.sup.1 and R.sup.2, which may be the same or different, each represent a phenyl group, a methyl group, a hydrogen atom, etc.; and R.sup.3 represents a benzoyl group, a urethane derivative residue, a hydrogen atom, etc., provided that R.sup.1, R.sup.2 and R.sup.3 are not simultaneously a hydrogen atom, represented by formula (IV): ##STR4## wherein R.sup.1, R.sup.2, and R.sup.3 are as defined above, are known, as disclosed in Ber. d. D. Chem. Gesellschaft Vol. 59B, p. 1742 (1926), Tetrahedron Lett., No. 34, p. 3295 (1967), and Synthesis, p. 482 (1976). However, each of these processes requires an expensive or highly toxic reagent, such as activated manganese dioxide, lead tetraacetate, silver oxide or potassium ferricyanide, in excess, e.g., in an amount of 2 to 5 equivalents to the 1,2-bishydrazone derivative. Therefore, the processes not only incur increased production cost but give rise to an environmental problem in disposal of waste water. In addition, the publications have no mention of synthesis of unsubstituted 1-amino-1,2,3-triazole by ring closure of unsubstituted glyoxal bishydrazone.
An object of the present invention is to provide a process for preparing 1-amino-1,2,3-triazole on an industrial scale which is safe, easy to carry out, and economical with solving the problems caused by the conventional techniques.


Disclosure of Invention

(1) The present invention relates to a process for preparing 1-amino-1,2,3-triazole represented by formula (III): ##STR5## comprising cyclizing glyoxal bishydrazone represented by formula (I): ##STR6## by reaction with an aqueous hydrogen peroxide solution in the presence of a catalytic amount of a transition metal oxide represented by formula (II): same or different, each represent an integer of 1 to 5.
(2) The present invention also relates to a process for preparing 1-amino-1,2,3-triazole represented by formula (III) in the above process (1), which comprises cyclizing glyoxal bishydrazone represented by formula (I) by reaction with manganese dioxide.
The steps involved for the preparation of 1,2,3-triazole via 1-amino-1,2,3-triazole (III) prepared by the process of the present invention are illustrated by the following reaction scheme: ##STR7##
Glyoxal bishydrazone (I) which is used as a starting material in the present invention is a known compound and can be synthesized in accordance with, e.g., the process described in Chem. Ber., Vol. 101, p. 1594 (1968). In some detail, glyoxal bishydrazone (I) can be obtained by reacting glyoxal (VI) or an aqueous solution thereof with hydrazine monohydrate (VII) or an aqueous solution thereof with or without a solvent. The resulting glyoxal bishydrazone (I) may be used either as prepared

REFERENCES:
Adv. in Heterocyclic. Chem., 53, 113 (1992).
Zh. Org. Khim. 28, 1320 (1992).
Ber., 42, 659 (1909).
Ber., 59B, 1742 (1926).
Tetrahedron Lett., No. 34, 3295 (1967).
Synthesis, 482 (1976).
J. Chem. Soc., Perkin Trans. I., 1 (1975).

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