Process for producing 1,3-oxazolidine derivatives

Details Process for producing 1,3-oxazolidine derivatives Process for producing 1,3-oxazolidine derivatives

2000-01-27

2001-08-07

Lambkin, Deborah C. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S215000

Reexamination Certificate

active

06271387

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to 1,3-oxazolidine derivatives, which are useful as, for example, pharmaceuticals, agrochemicals, and other fine chemicals or intermediates thereof.
2. Description of the Related Art
As examples of production processes for 1,3-oxazolidine derivatives, a process of reacting a &bgr;-aminoalcohol derivative with an aldehyde, and a process of reacting an ethyleneimine derivative with an aldehyde are known. These processes, however, require &bgr;-aminoalcohol derivatives or ethyleneimine derivatives as materials which may not be significantly available, and therefore are not always satisfactory for general purpose use and are insufficient in yields.
SUMMARY OF THE INVENTION
Accordingly, it is an object of the present invention to provide a process capable of easily obtaining 1,3-oxazolidine derivatives from readily available materials.
It is another object of the invention to provide a process for producing 1,3-oxazolidine derivatives, which process is satisfactory for general purpose use.
A further object of the invention is to provide a process for obtaining 1,3-oxazolidine derivatives in good yields.
After intensive investigations to achieve the above objects, the present inventors found that a reaction between an imine derivative and an epoxy compound can efficiently yield a corresponding 1,3-oxazolidine derivative. The invention has been accomplished on the basis of the above findings.
Specifically, the invention provides, in an aspect, a process for producing 1,3-oxazolidine derivatives, which process includes the step of reacting an imine derivative of the following formula (1):
wherein R
1
and R
2
are each, identical to or different from each other, a hydrogen atom, a hydrocarbon group or a heterocyclic group, R
3
is a hydrogen atom, a hydrocarbon group, a heterocyclic group, a hydroxyl group, a substituted oxy group, or an amino group which may have a substituent, where R
1
and R
2
may be combined to form a ring with the adjacent carbon atom, with an epoxy compound of the following formula (2):
wherein R
4
, R
5
, R
6
, and R
7
are each, identical to or different from one another, a hydrogen atom, a hydrocarbon group or a heterocyclic group, where each combination of R
4
and R
5
, R
6
and R
7
, or R
4
and R6 may be combined to form a ring with the adjacent carbon atom or the adjacent carbon-carbon bond, to yield an oxazolidine derivative of the following formula (3):
wherein R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, and R
7
have the same meanings as defined above.
The reaction may be performed in the presence of, for example, a compound of a Group 3 element of the Periodic Table of Elements, or another metallic compound catalyst.
The term “imine derivative” as used herein means and includes not only imine compounds in a narrow meaning but also oximes, oxime ethers, hydrazone derivatives, and other various compounds each having a C═N bond.
DESCRIPTION OF THE PREFERRED EMBODIMENT
[Imine Derivative]
In the formula (1), the hydrocarbon group in R
1
, R
2
, and R3 includes aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed from these groups combined together. Such aliphatic hydrocarbon groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, hexyl, decyl, and other alkyl groups each having about 1 to 10 (preferably 1 to 6, and more preferably 1 to 4) carbon atoms; vinyl, allyl, 1-butenyl, and other alkenyl groups each having about 2 to 10 (preferably 2 to 6, and more preferably 2 to 4) carbon atoms; ethynyl, propynyl, and other alkynyl groups each having about 2 to 10 (preferably 2 to 6, and more preferably 2 to 4) carbon atoms.
The alicyclic hydrocarbon groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, and other cycloalkyl groups each having about 3 to 12 (preferably 3 to 8, and more preferably 5 or 6) members; cyclopentenyl, cyclohexenyl, and other cycloalkenyl groups each having about 3 to 12 (preferably 3 to 8, and more preferably 5 or 6) members. Examples of the aromatic hydrocarbon groups are phenyl and naphthyl groups.
Such hydrocarbon groups formed from an aliphatic hydrocarbon group and an alicyclic hydrocarbon group combined together include, but are not limited to, cyclopentylmethyl, cyclohexylmethyl, 2-cyclohexylethyl, and other C
3
-C
12
cycloalkyl-C
1
-C
4
alkyl groups, and other cycloalkyl-alkyl groups. Examples of hydrocarbon groups formed from an aliphatic hydrocarbon group and an aromatic hydrocarbon group combined together are C
7
-C
4
aralkyl groups, and other aralkyl groups; and a phenyl group substituted with about one to four C
1
-C
4
alkyl groups, and other alkyl-substituted aryl groups.
Preferred hydrocarbon groups include, for example, C
1
-C
10
alkyl groups, C
2
-C
10
alkenyl groups, C
2
-C
10
alkynyl groups, C
6
-C
10
aromatic hydrocarbon groups, C
3
-C
12
cycloalkyl-C
1
-C
4
alkyl groups, and C
7
-C
14
aralkyl groups.
The hydrocarbon groups may have a variety of substituents, such as a halogen atom, an oxo group, a hydroxyl group, substituted oxy groups (e.g., alkoxy groups, aryloxy groups, aralkyloxy groups, and acyloxy groups), a carboxyl group, substituted oxycarbonyl groups, substituted or unsubstituted carbamoyl groups, a cyano group, a nitro group, substituted or unsubstituted amino groups, and heterocyclic groups.
Heterocyclic rings to constitute the heterocyclic group in R
1
, R
2
, and R
3
include aromatic heterocyclic rings and non-aromatic heterocyclic rings. Such heterocyclic rings include, but are not limited to, heterocyclic rings each having an oxygen atom as a hetero atom, heterocyclic rings each having a sulfur atom as a hetero atom, and heterocyclic rings each having a nitrogen atom as a hetero atom. Examples of the oxygen-containing heterocyclic rings are furan, tetrahydrofuran, oxazole, isoxazole, and other 5-membered rings; 4-oxo-4H-pyran, tetrahydropyran, morpholine, and other 6-membered rings; and benzofuran, isobenzofuran, 4-oxo-4H-chromene, chroman, isochroman, and other condensed rings. The sulfur-containing heterocyclic rings include, but are not limited to, thiophene, thiazole, isothiazole, thiadiazole, and other 5-membered rings; 4-oxo-4H-thiopyran, and other 6-membered rings; and benzothiophene and other condensed rings. Examples of the nitrogen-containing heterocyclic rings include pyrrole, pyrrolidine, pyrazole, imidazole, triazole, and other 5-membered rings; pyridine, pyridazine, pyrimidine, pyrazine, piperidine, piperazine, and other 6-membered rings; and indole, indoline, quinoline, acridine, naphthyridine, quinazoline, purine, and other condensed rings. The heterocyclic rings may each have a substituent. Such substituents include, for example, those as exemplified in the description of the hydrocarbon groups, alkyl groups (e.g., methyl, ethyl, and other C
1
-C
4
alkyl groups), cycloalkyl groups, and aryl groups (e.g., phenyl and naphthyl groups).
As rings formed by R
1
and R
2
combined together with the adjacent carbon atom, there may be mentioned cyclobutane, cyclopentane, cyclohexane, cyclohexene, cyclooctane, cyclododecane, and other non-aromatic carbocyclic rings (cycloalkane rings and cycloalkene rings) and non-aromatic heterocyclic rings each having about 3 to 20 (preferably 3 to 15, and more preferably 5 to 12) members. These rings may have any of the aforementioned substituents, and to these rings, another ring (a non-aromatic or aromatic ring) may be condensed.
The substituted oxy groups in R
3
include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutyloxy, and other alkoxy groups (preferably, C
1
-C
10
alkoxy groups, and more preferably, C
1
-C
6
alkoxy groups) phenoxy group, and other aryloxy groups; and benzyloxy, 2-phenylethyloxy, and other aralkyloxy groups. Examples of the amino group which may have a substituent in R
3
include amino group; methylamino, dimethylamino, ethylamino, di

Affiliated with

Also associated with

Rating

Process for producing 1,3-oxazolidine derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for producing 1,3-oxazolidine derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for producing 1,3-oxazolidine derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2474569