Process for preparing 1-substituted 4-cyano-1,2,3-triazoles

Details Process for preparing 1-substituted 4-cyano-1,2,3-triazoles Process for preparing 1-substituted 4-cyano-1,2,3-triazoles

2000-10-18

2001-08-21

Morris, Patricia L. (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06277999

ABSTRACT:

BACKGROUND OF THE INVENTION
1-Substituted 1H-1,2,3-triazoles are widely used industrially. For example, the European Patent Applications with the publication nos. 114347 A2 (EP 114347) and 199262 A1 (EP 199262) describe appropriate triazoles having anticonvulsive action. Compounds of this type are prepared, for example, by reaction of an arylalkyl azide with an alkyne derivative followed, if desired, by subsequent chemical conversions. Actual embodiments can be seen, for example, from the working examples of EP 199262 and EP 11 4347.
It is the aim of a variety of efforts to develop for pharmaceutical active ingredients production processes which are easy to manipulate and economical, result in high yields and ecologically have as few objections as possible.
The invention relates to a novel process for the preparation of 1-substituted 1H-1,2,3-triazole-4-carbonitriles, to novel intermediates and to their use for the production, for example, of pharmaceutical active ingredients.
DESCRIPTION OF THE INVENTION
The invention relates on the one hand to a novel preparation of compounds of the formula (I)
in which R
1
is an aromatic or heteroaromatic radical, aromatic-aliphatic or heteroaromatic-aliphatic radical, a heterocyclic radical, a cycloaliphatic radical, a cycloaliphatic-aliphatic radical or an aliphatic radical, and on the other hand to novel compounds of the formula (I).
An aromatic radical is, for example, mono- or bicyclic carbocyclic aryl which is unsubstituted or mono- or polysubstituted, such as di- or trisubstituted, for example phenyl, naphthyl or biphenylyl.
A heteroaromatic radical is, for example, mono- bi- or tricyclic heteroaryl, for example a 5- or 6-membered and monocyclic radical, which contains-up to and including four identical or different heteroatoms, such as oxygen, sulfur or nitrogen, preferably 1, 2, 3 or 4 nitrogen atoms, an oxygen or a sulfur atom.
Suitable 5-membered heteroaryl radicals are, for example, monoaza-, diaza-, triaza-, tetraaza-, monooxa- or monothiacyclic heteroaryl radicals, such as pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furyl and thienyl, while possible 6-membered radicals are, in particular, pyridyl radicals.
In an aromatic-aliphatic radical, the aromatic moiety, for example, has the meaning which is indicated above for aromatic radicals, while an aliphatic radical is, for example, lower alkyl, lower alkenyl or lower alkynyl. An aromatic-aliphatic radical is, for example, phenyl-lower alkyl, phenyl-lower alkenyl or phenyl-lower alkynyl, furthermore naphthyl-lower alkyl.
In a heteroaromatic-aliphatic radical, the heteroaromatic moiety, for example, has the meaning which is indicated above for heteroaromatic radicals, while an aliphatic radical is, for example, lower alkyl, lower alkenyl or lower alkynyl. A heteroaromatic-aliphatic radical is, for example, pyridyl-lower alkyl.
A heterocyclic radical is, for example, a 5- or 6-membered monocyclic or a bi- or tricyclic radical which contains up to and including four identical or different heteroatoms, such as nitrogen, oxygen or sulfur, preferably one, two or three nitrogen atoms, a sulfur and an oxygen atom. It is also possible for one or two benzene rings to be fused to an appropriate heterocyclic radical. A heterocyclic radical of this type, for example, is a partially hydrogenated 2-oxobenzazepine, such as 2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine.
A cycloaliphatic radical is, for example, cycloalkyl or furthermore cycloalkenyl, which in each case are unsubstituted or mono- or polysubstituted, e.g. disubstituted, e.g. by lower alkyl, carboxyl or lower alkoxycarbonyl. A cycloaliphatic-aliphatic radical is, for example, cycloalkyl-lower alkyl or furthermore cycloalkenyl-lower alkyl.
An aliphatic radical is, for example, lower alkyl, lower alkenyl or furthermore lower alkynyl, which are unsubstituted or in each case mono-or polysubstituted, e.g. disubstituted, e.g. by halogen, by free or esterified or amidated carboxyl, such as lower alkoxycarbonyl, carbamoyl or mono- or di-lower alkylated carbamoyl, by hydroxyl which can also be etherified, by S(O)
m
—R
0
or by a hydrocarbon radical, such as lower alkyl, lower alkenyl or lower alkynyl, which in turn can be unsubstituted or substituted, for example by halogen or hydroxyl; m being 0, 1 or 2 and R
0
being an aliphatic radical. Etherified hydroxyl is, in particular, lower alkoxy or lower alkenyloxy, furthermore phenyl-lower alkoxy and phenoxy.
Aromatic and heteroaromatic radicals can be unsubstituted or mono- or polysubstituted, e.g. di- or trisubstituted, for example by substituents selected from: halogen, hydroxyl which can also be etherified, S(O)
m
—R
0
and a hydrocarbon radical which in turn can be unsubstituted or substituted, for example by halogen or hydroxyl; m being 0, 1 or 2 and R
0
being an aliphatic radical.
If not defined differently, the general definitions used above and below have the following meanings:
The expression “lower” means that appropriate groups and compounds in each case in particular contain up to and including 7, preferably up to and including 4, carbon atoms.
Naphthyl is 1- or 2-naphthyl.
Biphenylyl is 2-, 3- or, in particular, 4-biphenylyl.
Pyrrolyl is, for example, 2- or 3-pyrrolyl. Pyrazolyl is 3- or 4-pyrazolyl. Imidazolyl is 2- or 4-irmidazolyl. Triazolyl is, for example, 1H-1,2,4-triazol-2-yl or 1,3,4-triazol-2-yl. Tetrazolyl is, for example, 1,2,3,4-tetrazol-5yl, furyl is 2- or 3-furyl and thienyl is 2- or 3-thienyl, while pyridyl can be 2-, 3- and 4-pyridyl.
Lower alkyl is in particular C
1
-C
7
alkyl, e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and furthermore includes corresponding pentyl, hexyl and heptyl radicals. C
1
-C
4
alkyl is preferred.
Lower alkenyl is in particular C
3
-C
7
alkenyl and is for example, 2-propenyl or 1-, 2- or 3-butenyl. C
3
-C
5
alkenyl is preferred.
Lower alkynyl is in particular C
3
-C
7
alkynyl and is preferably propargyl.
Phenyl lower alkyl is in particular phenyl-C
1
-C
4
alkyl and is preferably benzyl, 1- and 2-phenethyl, while phenyl-lower alkenyl and phenyl-lower alkynyl are in particular phenyl- C
3
-C
5
alkenyl and -alkynyl, in particular 3-phenylallyl and 3-phenylpropargyl.
Naphthyl-lower alkyl is in particular naphthyl-C
1
-C
4
alkyl and is, for example, 1- or 2-naphthylmethyl, -ethyl, -n-propyl or -n-butyl.
Pyridyl-lower alkyl is in particular pyridyl-C
1
-C
4
alkyl and is, for example, 2-, 3- or 4-pyridylmethyl, -ethyl, -n-propyl or -n-butyl.
Cycloalkyl is, for example, C
3
-C
8
cycloalkyl, which can be unsubstituted or substituted, for example by lower alkyl and is, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. Cyclopentyl and cyclohexyl are preferred.
Cycloalkenyl is in particular C
3
-C
7
cycloalkenyl and is preferably cyclopent-2-enyl, cyclopent-3-enyl, cyclohex-2-enyl and cyclohex-3-enyl.
Cycloalkyl-lower alkyl is in particular C
3
-C
8
cycloalkyl-C
1
-C
4
alkyl and is, for example, cyclopentyl- or cyclohexylmethyl or -ethyl, while cycloalkyl-lower alkenyl is in particular C
3
-C
8
cycloalkyl-C
3
-C
4
alkenyl and is, for example, cyclopentyl- or cyclohexylprop-2-enyl or cyclo-2-butenyl.
Lower alkoxy is in particular C
1
-C
7
alkoxy and is, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy and furthermore includes corresponding pentyloxy, hexyloxy and heptyloxy radicals. C
1
-C
4
alkoxy is preferred.
Lower alkenyloxy is in particular C
3
-C
7
alkenyloxy and is, for example, allyloxy or but-2-enyloxy or but-3-enyloxy. C
3
-C
5
alkenyloxy is preferred.
Phenyl-lower alkoxy is in particular phenyl-C
1
-C
4
alkoxy, such as benzyloxy, 1- or 2-phenylethoxy, 3-phenylpropyloxy or 4-phenylbutyloxy.
Lower alkoxycarbonyl is in particular C
2
-C
8
alkoxycarbonyl and is, for example, methoxy-, ethoxy-, propyloxy- or pivaloyloxycarbonyl. C
2
-C
5
alkoxycarbonyl is preferred.
Halogen is in particular fluorine, chlorine or bromine, and furthermore includes iodine.
Japanese Patent Application J 56 127-363 describes a syn

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