1. 4-Methyltetrahydro1,3oxazolo2,3-b1,3oxazol-4-ium derivatives of the general formula (1),
wherein:
R1 is phenyl; 2-nitrophenyl; 3-nitrophenyl; 4-nitrophenyl; 2-bromophenyl; 3-bromophenyl; 4-bromophenyl; 2,3-dibromophenyl; 2,4-dibromophenyl; 2-chlorophenyl; 3-chlorophenyl; 4-chlorophenyl; 2,4-dichlorophenyl; 3,4-dichlorophenyl; 3,5-dichlo-rophenyl; 2,6-dichlorophenyl; 2-iodophenyl; 4-iodophenyl; 2-methoxyphenyl; 3-methoxyphenyl; 4-methoxyphenyl; 2,5-dimethoxyphenyl; 3,4-dimethoxyphenyl; 2,3,4-trimethoxyphenyl; 3,4,5-trimethoxyphenyl; 2-methylphenyl; 3-methylphenyl; 4-methylphenyl; 3,5-dimethylphenyl; 2,4-dimethylphenyl; 2-fluorophenyl; 3-fluorophenyl; 4-fluorophenyl; 3,4-difluorophenyl; 2,3-difluorophenyl; 3,5-difluorophenyl; 2,4-difluorophenyl; 2,3,4,5-tetrafluorophenyl; 2-(methoxycarbonyl)phenyl; 3-(methoxycarbonyl)phenyl; 4-(methoxycarbonyl)phenyl; 2-(trifluoromethyl)phenyl; 3-(trifluoromethyl)phenyl; 4-(trifluoromethyl)phenyl; 4-tert-butylphenyl; 2-phenylophenyl; 3-phenylophenyl; 4-phenylophenyl; 4-benzoylphenyl; 4-benzyloxyphenyl; 4-(methylsulphonyl)phenyl; 2-cyanophenyl; 3-cyanophenyl; 4-cyanophenyl; 4-formylphenyl; 4-methylthiophenyl; 3-phenoxyphenyl; 4-phenoxyphenyl; 2,4-diphenoxyphenyl; 2,4-dinitrophenyl; 4-(aminosulfonyl)phenyl; 2-pyridyl; 3-pyridyl; 4-pyridyl; 2-furyl; 2-thienyl; 2-benzobfuryl; 1-naphthyl or 2-naphthyl;
X is chloride, bromide or iodide,
or
bis{4-methyltetrahydro1,3oxazolo2,3-b1,3oxazol-4-ium} derivatives of the general formula (3),
wherein:
R3 is benzene-1,4-diyl; benzene-1,3-diyl; 1,2-dioxoethan-1,2-diyl; biphenyl-4,4\u2032-diyl; methanediyldibenzene-4,1-diyl; oxodibenzene-4,1-diyl or carbonyldibenzene-4,1-diyl;
X is chloride, bromide or iodide,
or
tris{4-methyltetrahydro1,3oxazolo2,3-b1,3oxazol-4-ium} derivatives of the general formula (5),
wherein:
R5 is benzene-1,3,5-triyl;
X is chloride, bromide or iodide.
2. 4-(2-Oxoethyl)tetrahydro1,3oxazolo2,3-b1,3oxazol-4-ium derivatives of the general formula (2),
wherein:
R2 is phenyl; 2-fluorophenyl; 3-fluorophenyl; 4-fluorophenyl; 2,4-difluorophenyl; 2,5-difluorophenyl; 2,6-difluorophenyl; 2,3,4-trichlorophenyl; 2,3,4,5-tetrafluorophenyl; 2-chlorophenyl; 3-chlorophenyl; 4-chlorophenyl; 2,4-dichlorophenyl; 3,4-dichlorophenyl; 2,5-dichlorophenyl; 2-bromophenyl; 3-bromophenyl; 4-bromophenyl; 3-iodophenyl; 4-iodophenyl; 2-hydroxyphenyl; 3-hydroxyphenyl; 4-hydroxyphenyl; 2,4-dihydroxyphenyl; 2,3-dihydroxyphenyl; 3,4-dihydroxyphenyl; 2,5-dihydroxyphenyl; 2-(acetyloxy)phenyl; 3-(acetyloxy)phenyl; 4-(acetyloxy)phenyl; 2,4-bis(acetyloxy)phenyl; 3,4-bis(acetyloxy)phenyl; 2,5-bis(acetyloxy)phenyl; 1,3-benzodioxol-5-yl; 2-phenylophenyl; 3-phenylophenyl; 4-phenylophenyl; 2-nitrophenyl; 3-nitrophenyl; 4-nitrophenyl; 2,4-dinitrophenyl; 3,4-dinitrophenyl; 2,5-dinitrophenyl; 4-chloro-3-nitrophenyl; 2-chloro-3-nitrophenyl; 2-methylphenyl; 3-methylphenyl; 4-methylphenyl; 2,4-dimethylphenyl; 3,4-dimethylphenyl; 2-methoxyphenyl; 3-methoxyphenyl; 4-methoxyphenyl; 3,4-dimethoxyphenyl; 2,4-dimethoxyphenyl; 2,5-dimethoxyphenyl; 3,4,5-trimethoxyphenyl; 4-ethylphenyl; 3-benzyloxyphenyl; 4-benzyloxyphenyl; 4-phenoxyphenyl; 2-cyanophenyl; 3-cyanophenyl; 4-cyanophenyl; 2-aminophenyl; 3-aminophenyl; 4-aminophenyl; 3-(trifluoromethyl)phenyl; 4-(trifluoromethyl)phenyl; 4-carbamoylphenyl; 4-sulfamoylphenyl; 4-(methylsulfonyl)phenyl; 4-(methoxycarbonyl)phenyl; 4-(acetylamino)phenyl; 4-(N,N-dimethylamino)phenyl; 4-tert-bu-.tylphenyl; trifluoromethyl; trichloromethyl; 2-pyridyl; 3-pyridyl; 4-pyridyl; 1-naphthyl; 2-naphthyl; 2-furyl; 2-benzobfuryl; 2-thienyl; amino; methylamino; dimethylamino; phenylamino; diphenylamino; benzylamino or dibenzylamino;
X is chloride, bromide or iodide,
or
bis{4-(2-oxoethyl)tetrahydro1,3oxazolo2,3-b1,3oxazol-4-ium} derivatives of general formula (4),
wherein:
R4 is benzene-1,4-diyl; benzene-1,3-diyl; biphenyl-4,4\u2032-diyl or oxydibenzene-4,1-diyl;
X is chloride, bromide or iodide.
3. The process for the preparation of 4-methyltetrahydro1,3oxazolo2,3-b1,3oxazol-4-ium derivatives of general formula (1) of claim 1,
comprising the reaction of a compound of general formula (6),
with tetrahydro1,3oxazolo2,3-ti1,3oxazole of formula (7),
wherein:
R1 is non-substituted or substituted group selected from alkyl, cycloalkyl, aryl, or heteroaryl, wherein substituted group denotes group substituted with radical independently selected from alkyl, aryl, acyl, alkoxyl, aryloxyl, alkoxycarbonyl, aryloxycarbonyl, halogen, cyano, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, amino-sulfonyl, nitro, amino, mono- or dialkylamino, mono- or diarylamino or acylamino;
X is fluoride, chloride, bromide, iodide or methanesulfonate.
4. The process according to claim 3, wherein:
R1 is phenyl; 2-nitrophenyl; 3-nitrophenyl; 4-nitrophenyl; 2-bromophenyl; 3-bromophenyl; 4-bromophenyl; 2,3-dibromophenyl; 2,4-dibromophenyl; 2-chlorophenyl; 3-chlorophenyl; 4-chlorophenyl; 2,4-dichlorophenyl; 3,4-dichlorophenyl; 3,5-di-chlorophenyl; 2,6-dichlorophenyl; 2-iodophenyl; 4-iodophenyl; 2-methoxyphenyl; 3-methoxyphenyl; 4-methoxyphenyl; 2,5-dimethoxyphenyl; 3,4-dimethoxyphenyl; 2,3,4-trimethoxyphenyl; 3,4,5-trimethoxyphenyl; 2-methylphenyl; 3-methylphenyl; 4-methylphenyl; 3,5-dimethylphenyl; 2,4-dimethylphenyl; 2-fluorophenyl; 3-fluorophenyl; 4-fluorophenyl; 3,4-difluorophenyl; 2,3-difluorophenyl; 3,5-difluorophenyl; 2,4-difluorophenyl; 2,3,4,5-tetrafluorophenyl; 2-(methoxycarbonyl)phenyl; 3-(me-thoxycarbonyl)phenyl; 4-(methoxycarbonyl)phenyl; 2-(trifluoromethyl)phenyl; 3-(trifluoromethyl)phenyl; 4-(trifluoromethyl)phenyl; 4-tert-butylphenyl; 2-phenylophenyl; 3-phenylophenyl; 4-phenylophenyl; 4-benzoylphenyl; 4-benzyloxyphenyl; 4-(methylsulphonyl)phenyl; 2-cyanophenyl; 3-cyanophenyl; 4-cyanophenyl; 4-formylphenyl; 4-methylthiophenyl; 3-phenoxyphenyl; 4-phenoxyphenyl; 2,4-diphenoxyphenyl; 2,4-dinitrophenyl; 4-(aminosulfonyl)phenyl; 2-pyridyl; 3-pyridyl; 4-pyridyl; 2-furyl; 2-thienyl; 2-benzobfuryl; 1-naphthyl or 2-naphthyl;
X is chloride, bromide or iodide.
5. The process for the preparation of 4-(2-oxoethyl)tetrahydro1,3oxazolo2,3-ti1,3oxa-zol-4-ium derivatives of general formula (2) of claim 2,
comprising the reaction of a compound of general formula (8),
with tetrahydro1,3oxazolo2,3-61,3oxazole of formula (7),
wherein:
R2 is non-substituted or substituted group selected from alkyl, cycloalkyl, aryl, heteroaryl, amino, mono- or dialkylamino, mono- or diarylamino or acylamino, wherein substituted group denotes group substituted with radical independently selected from alkyl, aryl, acyl, alkoxyl, aryloxyl, alkoxycarbonyl, aryloxycarbonyl, halogen, cyano, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, aminosulfonyl, nitro, amino, mono- or dialkylamino, mono- or diarylamino or acylamino;
X is fluoride, chloride, bromide, iodide or methanesulfonate.
6. The process according to claim 5, wherein:
R2 is phenyl; 2-fluorophenyl; 3-fluorophenyl; 4-fluorophenyl; 2,4-difluorophenyl; 2,5-difluorophenyl; 2,6-difluorophenyl; 2,3,4-trichlorophenyl; 2,3,4,5-tetrafluorophenyl; 2-chlorophenyl; 3-chlorophenyl; 4-chlorophenyl; 2,4-dichlorophenyl; 3,4-dichlorophenyl; 2,5-dichlorophenyl; 2-bromophenyl; 3-bromophenyl; 4-bromophenyl; 3-iodophenyl; 4-iodophenyl; 2-hydroxyphenyl; 3-hydroxyphenyl; 4-hydroxyphenyl; 2.4-dihydroxyphenyl; 2,3-dihydroxyphenyl; 3,4-dihydroxyphenyl; 2,5-dihydroxyphenyl; 2-(acetyloxy)phenyl; 3-(acetyloxy)phenyl; 4-(acetyloxy)phenyl; 2,4-bis(acetyloxy)phenyl; 3,4-bis(acetyloxy)phenyl; 2,5-bis(acetyloxy)phenyl; 1,3-benzodioxol-5-yl; 2-phenylophenyl; 3-phenylophenyl; 4-phenylophenyl; 2-nitrophenyl; 3-nitrophenyl; 4-nitrophenyl; 2,4-dinitrophenyl; 3,4-dinitrophenyl; 2,5-dinitrophenyl; 4-chloro-3-nitrophenyl; 2-chloro-3-nitrophenyl; 2-methylphenyl; 3-methylphenyl; 4-methylphenyl; 2,4-dimethylphenyl; 3,4-dimethylphenyl; 2-methoxyphenyl; 3-methoxyphenyl; 4-methoxyphenyl; 3,4-dimethoxyphenyl; 2,4-dimethoxyphenyl; 2.5-dimethoxyphenyl; 3,4,5-trimethoxyphenyl; 4-ethylphenyl; 3-benzyloxyphenyl; 4-benzyloxyphenyl; 4-phenoxyphenyl; 2-cyanophenyl; 3-cyanophenyl; 4-cyanophenyl; 2-aminophenyl; 3-aminophenyl; 4-aminophenyl; 3-(trifluoromethyl)phenyl; 4-(trifluoromethyl)phenyl; 4-carbamoylphenyl; 4-sulfamoylphenyl; 4-(methylsulfonyl)phenyl; 4-(methoxycarbonyl)phenyl; 4-(acetylamino)phenyl; 4-(N,N-dimethylamino)phenyl; 4-tert-butylphenyl; trifluoromethyl; trichloromethyl; 2-pyridyl; 3-pyridyl; 4-pyridyl; 1-naphthyl; 2-naphthyl; 2-furyl; 2-benzobfuryl; 2-thienyl; amino; methylamino; dimethylamino; phenylamino; diphenylamino; benzylamino or dibenzylamino;
X is chloride, bromide or iodide.
7. The process for the preparation of bis {4-methyltetrahydro1,3oxazolo2,3-b1,3oxazol-4-ium} derivatives of general formula (3) of claim 1,
comprising the reaction of a compound of general formula (9),
with tetrahydro1,3oxazolo2,3-b1,3oxazole of formula (7),
wherein:
R3 is non-substituted or substituted group selected from alkyl, cycloalkyl, aryl or heteroaryl, wherein substituted group denotes group substituted with radical independently selected from alkyl, aryl, acyl, alkoxyl, aryloxyl, alkoxycarbonyl, aryloxycarbonyl, halogen, cyano, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, amino-sulfonyl, nitro, amino, mono- or dialkylamino, mono- or diarylamino or acylamino;
X is fluoride, chloride, bromide, iodide or methanesulfonate.
8. The process according to claim 7, wherein:
R3 is benzene-1,4-diyl; benzene-1,3-diyl; 1,2-dioxoethan-1,2-diyl; biphenyl-4,4\u2032-diyl; methanediyldibenzene-4,1-diyl; oxodibenzene-4,1-diyl or carbonyldibenzene-4,1-diyl;
X is chloride, bromide or iodide.
9. The process for the preparation of bis{4-(2-oxoethyl)tetrahydro1,3oxazolo2,3-b1,3-oxazol-4-ium} derivatives of general formula (4) of claim 2,
comprising the reaction of a compound of general formula (10),
with tetrahydro1,3oxazolo2,3-b1,3oxazole of formula (7),
wherein:
R4 is non-substituted or substituted group selected from alkyl, cycloalkyl, aryl, heteroaryl, amino, mono- or dialkylamino, mono- or diarylamino or acylamino, wherein substituted group denotes group substituted with radical independently selected from alkyl, aryl, acyl, alkoxyl, aryloxyl, alkoxycarbonyl, aryloxycarbonyl, halogen, cyano, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, aminosulfonyl, nitro, amino, mono- or dialkylamino, mono- or diarylamino or acylamino;
X is fluoride, chloride, bromide, iodide or methanesulfonate.
10. The process according to claim 9, wherein:
R4 is benzene-1,4-diyl; benzene-1,3-diyl; biphenyl-4,4\u2032-diyl or oxydibenzene-4,1-diyl;
X is chloride, bromide or iodide.
11. The process for the preparation of tris{4-methyltetrahydro1,3oxazolo2,3-61,3oxazol-4-ium} derivatives of general formula (5) of claim 1,
comprising the reaction of a compound of general formula (11),
with tetrahydro1,3oxazolo2,3-b1,3oxazole of formula (7),
wherein:
R5 is non-substituted or substituted group selected from alkyl, cycloalkyl, aryl or heteroaryl, wherein substituted group denotes group substituted with radical independently selected from alkyl, aryl, acyl, alkoxyl, aryloxyl, alkoxycarbonyl, aryloxycarbonyl, halogen, cyano, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, amino-sulfonyl, nitro, amino, mono- or dialkylamino, mono- or diarylamino or acylamino;
X is fluoride, chloride, bromide, iodide or methanesulfonate.
12. The process according to claim 11, wherein:
R3 is benzene-1,3,5-triyl;
X is chloride, bromide or iodide.
13. The process according to claim 3, wherein the reaction is carried out using approximately equimolar amount of both reactants.
14. The process according to claim 7, wherein the reaction is carried out using approximately double molar amount of tetrahydro1,3oxazolo2,3-b1,3oxazole with respect to compound of general formula (9).
15. The process according to claim 11, wherein the reaction is carried out using approximately triple molar amount of tetrahydro1,3oxazolo2,3-b1,3oxazole with respect to compound of general formula (11).
16. The process according to claim 3, wherein the reaction is carried out in an organic solvent at a temperature of room temperature to the boiling point of reaction mixture, but no higher than 120\xb0 C., for a time period of 10 min. to 7 days.
17. The process according to claim 16, wherein reaction is carried out at a temperature no higher than 70\xb0 C., for a time period of 30 min. to 3 days.
18. The process according to claim 16, wherein the reaction is carried out in an organic solvent selected from alcohols; ethers; chlorinated hydrocarbons; N,N-dialkylamides; sulfoxides; aromatic hydrocarbons; ketones; esters; nitriles; and mixtures thereof.
19. The process according to claim 18, wherein the reaction is carried out in an organic solvent selected from methanol; ethanol; n-propanol; isopropanol; dichloromethane; chloroform; diethyl ether; diisopropyl ether; tetrahydrofurane; benzene; toluene; acetonitrile; N,N-dimethylformamide; dimethyl sulfoxide; ethyl acetate and mixtures thereof.
20. The process according to claim 16, wherein after reaction, the solvent is removed by evaporation or filtration and then, resulting crude product is purified by recrystallization from a solvent selected from the group consisting of methanol; ethanol; isopropanol; acetonitrile and mixtures thereof.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A sensing circuit for a memory cell and comprising:
a first bias current generator connected between a first voltage reference and a first inner circuit node;
at least one second reference current generator connected to the first voltage reference;
a comparator having a first input terminal connected to a comparison circuit node that is connected to said at least one second reference current generator, a second input terminal connected to a circuit node that is connected to the first inner circuit node, and at least one output terminal forming at least one output terminal of the sensing circuit;
a cascode-configured bias circuit connected between the inner circuit node and a matching circuit node, said cascode-configured bias circuit also connected to a second voltage reference; and
a currentvoltage conversion stage connected to the matching circuit node, to the comparison circuit node, and to a third voltage reference.
2. A sensing circuit according to claim 1, wherein the first voltage reference is a supply voltage, and a third voltage reference is ground.
3. A sensing circuit according to claim 1, wherein said cascode-configured bias circuit comprises:
a first transistor connected between the inner circuit node and the matching circuit node, said first transistor comprising a control terminal; and
an operational amplifier having an output terminal connected to the control terminal of said first transistor, a first input terminal connected to the second voltage reference and a second input terminal connected to the output terminal.
4. A sensing circuit according to claim 3, wherein said first transistor comprises a P-channel MOS transistor.
5. A sensing circuit according to claim 1, wherein said currentvoltage conversion stage comprises:
a second transistor that is diode-configured and is connected between the matching circuit node and the third voltage reference, said second transistor comprising a control terminal; and
a third transistor connected between the comparison circuit node and the third voltage reference, said third transistor comprising a control terminal connected to the control terminal of said second transistor.
6. A sensing circuit according to claim 5, wherein said second transistor and said third transistor comprise N-channel MOS transistors.
7. A sensing circuit according to claim 1, wherein said at least one second reference current generator comprises a plurality of reference current generators forming a plurality of branches connected to a plurality of inputs of said comparator; and wherein said at least one output terminal of said comparator comprises a plurality of output terminals for forming a plurality of output terminals of the sensing circuit.
8. A memory comprising:
at least one memory cell; and
at least one sensing circuit connected to said at least one memory cell and comprising
a first bias current generator connected to a first voltage reference,
at least one second reference current generator connected to the first voltage reference,
a comparator having a first input terminal connected to a comparison circuit node that is connected to said at least one second reference current generator, a second input terminal connected to a circuit node that is connected to said first bias current generator, and at least one output terminal forming at least one output terminal of the sensing circuit,
a bias circuit connected to said first bias current generator, and
a currentvoltage conversion stage connected to said bias circuit, to the comparison circuit node, and to a second voltage reference.
9. A memory according to claim 8, wherein the first voltage reference is a supply voltage, and the second voltage reference is ground.
10. A memory according to claim 8, wherein said bias circuit comprises:
a first transistor connected between said first bias current generator and said currentvoltage conversion stage, said first transistor comprising a control terminal; and
an operational amplifier having an output terminal connected to the control terminal of said first transistor, a first input terminal connected to a third voltage reference and a second input terminal connected to the output terminal.
11. A memory according to claim 10, wherein said first transistor comprises a P-channel MOS transistor.
12. A memory according to claim 8, wherein said currentvoltage conversion stage comprises:
a second transistor that is diode-configured and is connected between said bias circuit and the second voltage reference, said second transistor comprising a control terminal; and
a third transistor connected between the comparison circuit node and the second voltage reference, said third transistor comprising a control terminal connected to the control terminal of said second transistor.
13. A memory according to claim 12, wherein said second transistor and said third transistor comprise N-channel MOS transistors.
14. A memory according to claim 8, wherein said at least one second reference current generator comprises a plurality of reference current generators forming a plurality of branches connected to a plurality of inputs of said comparator; and wherein said at least one output terminal of said comparator comprises a plurality of output terminals for forming a plurality of output terminals of said sensing circuit.
15. A method for forming a sensing circuit for a memory cell, the method comprising:
connecting a first bias current generator between a first voltage reference and a first inner circuit node;
connecting at least one second reference current generator to the first reference voltage;
connecting a comparator having a first input terminal to a comparison circuit node that is connected to the at least one second reference current generator, a second input terminal connected to a circuit node that is connected to the first inner circuit node, and at least one output terminal forming at least one output terminal of the sensing circuit;
connecting a bias circuit between the inner circuit node and a matching circuit node, the bias circuit also being connected to a second voltage reference; and
connecting a currentvoltage conversion stage to the matching circuit node, to the comparison circuit node, and to a third voltage reference.
16. A method according to claim 15, wherein the first voltage reference is a supply voltage, and the third voltage reference is ground.
17. A method according to claim 15, wherein the bias circuit comprises:
a first transistor connected between the inner circuit node and the matching circuit node, the first transistor comprising a control terminal; and
an operational amplifier having an output terminal connected to a control terminal of the first transistor, a first input terminal connected to the third voltage reference and a second input terminal connected to the output terminal.
18. A method according to claim 17, wherein the first transistor comprises a P-channel MOS transistor.
19. A method according to claim 15, wherein the currentvoltage conversion stage comprises:
a second transistor that is diode-configured and is connected between the matching circuit node and the third voltage reference, the second transistor comprising a control terminal; and
a third transistor connected between the comparison circuit node and the third voltage reference, the third transistor comprising a control terminal connected to the control terminal of the second transistor.
20. A method according to claim 19, wherein the second transistor and the third transistor comprise N-channel MOS transistors.
21. A method according to claim 15, wherein the at least one second reference current generator comprises a plurality of reference current generators forming a plurality of branches connected to a plurality of inputs of the comparator; and wherein the at least one output terminal of the comparator comprises a plurality of output terminals for forming a plurality of output terminals of the sensing circuit.