Process for producing carbonyl hydrazones

Details Process for producing carbonyl hydrazones Process for producing carbonyl hydrazones

2001-10-26

2004-10-19

Raymoni, Richard L. (Department: 1624)

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C544S311000, C544S060000, C544S123000, C544S295000, C564S229000, C564S247000, C564S147000

Reexamination Certificate

active

06806367

ABSTRACT:

The present invention relates to a process for producing carbonyl hydrazones, their intermediates and the like.
BACKGROUND OF THE INVENTION
Certain herbicidal compounds such as 1-amino-3-substituted-phenyl-2,4(1H,3H)-pyrimidinediones and processes for their preparations are disclosed in WO98/41093, and the like.
It has been required that these compounds can be produced by using appropriate processes for industrial exploitations in terms of yields, raw materials, reaction steps, reaction operations, economical stand points etc.
The present inventors have conducted researches and investigations for these processes. As a result, they have obtained facts and discoveries that these compounds can be prepared using certain rearrangement reactions of substituted aminooxy compounds and that such rearrangement reactions are novel.
SUMMARY OF THE INVENTION
The first aspect of the present invention is to provide a method for producing carbonyl hydrazones of the formula (I) or their salts:
wherein each of R
1
and R
2
is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, OR
3
, SR
3
, COR
3
, COOR
3
or cyano; R
3
is unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted aryl, or unsubstituted or substituted heteroaryl;
R
1
and R
2
may combine together with the adjacent carbon atom of ═CR
1
R
2
to form an unsubstituted or substituted cyclic ring;
each of R
4
and R
5
is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, NR
6
R
7
, OR
8
or SR
9
; each of R
6
, R
7
, R
8
and R
9
is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted alkylcarbonyl, unsubstituted or substituted alkenylcarbonyl, unsubstituted or substituted alkenylcarbonyl, unsubstituted or substituted arylcarbonyl, or unsubstituted or substituted heteroarylcarbonyl;
R
4
and R
5
may combine together with the adjacent skeleton of C/N bond to form a heterocyclic ring;
which comprises rearranging substituted aminooxy compounds of the formula (II) or their salts:
wherein R
1
, R
2
, R
4
and R
5
are as defined above.
The second aspect of the present invention is to provide a process for producing 1-substituted amino-2,4(1H,3H)-pyrimidinediones of the formula (I-a) or their salts:
wherein R
1
and R
2
are as defined above;
each of X and Y is hydrogen, halogen, cyano, nitro, thiocarbamoyl or haloalkyl;
Z is oxygen, sulfur or NR; R is hydrogen, alkyl, alkenyl or alkynyl;
Ar is unsubstituted or substituted aryl, or unsubstituted or substituted heteroaryl;
which comprises rearranging 2-(substituted aminooxy)-4-(3H) pyrimidinones of the formula (II-a) or their salts:
wherein R
1
, R
2
, X, Y, Z and Ar are as defined above.
Among the compounds of the formula (I), said 1-substituted amino-2,4(1H,3H)-pyrimidinediones of the formula (I-a) or their salts are useful in view of the preparation processes of herbicidal and/or desiccant compounds.
The third aspect of the present invention is to provide 2-(substituted-aminooxy)-4-(3H) pyrimidinones of the formula (II-a) or their salts, and to provide a process for producing 2-(substituted aminooxy)-4-(3H) pyrimidinones of the formula (II-a) or their salts:
which comprises reacting 2-halogeno-4-(3H) pyrimidinones of the formula (III-a) or their salts:
wherein Hal is halogen, X, Y, Z and Ar are as defined above, with oxime derivatives of the formula (IV) or their salts:
wherein R
1
and R
2
are as defined above.
The fourth aspect of the present invention is to provide 2-halogeno-4-(3H) pyrimidinones of the formula (III-a) or their salts, and to provide a process for producing 2-halogeno-4-(3H) pyrimidinones of the formula (III-a) or their salts:
which comprises reacting 2,4(1H,3H)-pyrimidinediones of the formula (V-a) or their salts:
wherein X, Y, Z and Ar are as defined above, with a halogenating agent.


REFERENCES:
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patent: 149242 (1985-07-01), None
March J., “Advanced Organic Chemistry—Reactions, Mechanisms, and Structure”, 4thEdition, (c) 1992, pp. 1141-1142.

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