Production process and intermediate of tetrazole compound

Details Production process and intermediate of tetrazole compound Production process and intermediate of tetrazole compound

1996-02-08

1999-02-23

Gerstl, Robert

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548250, 564 74, 564226, C07C25186

Patent

active

058745939

DESCRIPTION:

BRIEF SUMMARY
INDUSTRIAL FIELD FOR UTILIZATION

The present invention relates to production processes and intermediates of tetrazole compounds. More particularly, it relates to 2-(tetrazol-5-yl)-4-oxo-4H-benzopyran derivatives which are known to be pharmacologically useful from the viewpoint of their antagonistic action to leukotrienes such as leukotrienes C and D, and it also relates to 2-(tetrazol-5-yl)-1,1'-biphenyl derivatives which are known to be pharmacologically useful from the viewpoint of their antagonistic action to angiotensin II. Further, it relates to processes for producing 5-phenyltetrazole derivatives which are useful as intermediates of the biphenyl derivatives, and it also relates to intermediates which are useful in their production.


Prior Art

As the process for producing tetrazole compounds such as 2-(tetrazol-5-yl)-4-oxo-4H-benzopyran derivatives, 2-(tetrazol-5-yl)-1,1'-biphenyl derivative and 5-phenyltetrazole derivatives, there has been known a process with an azide such as sodium azide, trialkyl tin azide or trimethylsilyl azide.
However, since azides are reacted with water or acids to produce hydrogen azide having toxic and explosive properties, the concentration of hydrogen azide in the gas phase in the upper part of a reactor should be strictly controlled during the reaction. It has been known that azides are liable to form an explosive salt with heavy metals. Therefore, the application of such a process with an azide on an industrial scale is disadvantageous from the viewpoint of its safety. Further, tin reagents such as trialkyl tin azide have drawbacks that they require a complicated procedure for the isolation of a product because of its lipophilicity and that tin-containing waste matters are formed in large quantities.
As the process for producing 2-(tetrazol-5-yl)-1,1'-biphenyl derivatives or 5-phenyltetrazole derivatives, another process is described in J. Org. Chem., 1991, 56, pp. 2395-2400, in which process biphenylcarboxylic acids or phenylcarboxylic acids are converted into their amides with cyanoethylamine, followed by chlorination with phos- phorous pentachloride, and reaction with hydrazine and then with dinitrogen tetroxide gas.
This process, however, has disadvantages that the yield of a desired product is not satisfactory, that the step of deprotecting a cyanoethyl group used as a protecting group is needed, and that the production on an industrial scale finds difficulty in using phosphorous pentachloride.


Objects of the Invention

It is an object of the present invention to provide a process for producing tetrazole compounds with safety in an industrially favorable manner.
It is another object of the present invention to provide intermediates useful for the production of the tetrazole compounds.
These and other objects and excellent advantages will be understood from the following description.


SUMMARY OF THE INVENTION

The present inventors have intensively studied on a process for producing tetrazole compounds. As a result, they have found that the above problems can be solved and the desired products can be obtained with safety in an industrially favorable manner by a process through amidrazone compounds with nitrile compounds as the starting materials, and they have made further studies, thereby completing the present invention.
Thus, the present invention provides: ##STR2##
wherein R.sup.1 is as defined below, characterized in that a nitrile of general formula (2): with R.sup.2 or a phenyl group optionally substituted with X, in which R.sup.2 is a hydroxy group, a halogen atom, an R.sup.3 CONH group, a nitro group, a C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy group; R.sup.3 is a C.sub.1 -C.sub.20 alkyl group, a phenyl group, a phenyl-substituted (C.sub.1 -C.sub.20) alkyl group, a phenyl-substituted (C.sub.1 -C.sub.20) alkoxyphenyl group or a (C.sub.1 -C.sub.20) alkoxyphenyl group; X is a halogen atom, a phenyl group optionally substituted with Y, a C.sub.1 -C.sub.20 alkyl group, a phenyl-substituted (C.sub.1 -C.sub.20) alkyl group, a phenyl-substituted (C.s

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