RU2632661C2 - Method for producing 3-(o,m,n-halogenphenyl)-3,4-dihydro-2h-benzo[f][1,5,3]dithiazepines - Google Patents
Method for producing 3-(o,m,n-halogenphenyl)-3,4-dihydro-2h-benzo[f][1,5,3]dithiazepines Download PDFInfo
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- RU2632661C2 RU2632661C2 RU2016103462A RU2016103462A RU2632661C2 RU 2632661 C2 RU2632661 C2 RU 2632661C2 RU 2016103462 A RU2016103462 A RU 2016103462A RU 2016103462 A RU2016103462 A RU 2016103462A RU 2632661 C2 RU2632661 C2 RU 2632661C2
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- benzo
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- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- CCYNVVOVOYRANL-UHFFFAOYSA-N 2H-1,5,3-dithiazepine Chemical class C1SC=CSC=N1 CCYNVVOVOYRANL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- JRNVQLOKVMWBFR-UHFFFAOYSA-N 1,2-benzenedithiol Chemical compound SC1=CC=CC=C1S JRNVQLOKVMWBFR-UHFFFAOYSA-N 0.000 claims description 7
- 230000003993 interaction Effects 0.000 claims description 3
- YZDZYSPAJSPJQJ-UHFFFAOYSA-N samarium(3+);trinitrate Chemical compound [Sm+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YZDZYSPAJSPJQJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 abstract description 3
- 230000002255 enzymatic effect Effects 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract description 2
- 239000003446 ligand Substances 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000016507 interphase Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 150000002678 macrocyclic compounds Chemical class 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- IZJQZHQUHCETJA-UHFFFAOYSA-N 1,3,5-dithiazepane Chemical class C1CSCSCN1 IZJQZHQUHCETJA-UHFFFAOYSA-N 0.000 description 1
- CNZVQCYTFMIBMO-UHFFFAOYSA-N 1,3-bis(methoxymethyl)imidazolidin-2-one Chemical compound COCN1CCN(COC)C1=O CNZVQCYTFMIBMO-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- RXJJITIQUOXKLH-UHFFFAOYSA-N 3-(2-chlorophenyl)-2,4-dihydro-1,5,3-benzodithiazepine Chemical compound Clc1ccccc1N1CSc2ccccc2SC1 RXJJITIQUOXKLH-UHFFFAOYSA-N 0.000 description 1
- BEMHANGIWWUEJU-UHFFFAOYSA-N 3-(3-chlorophenyl)-2,4-dihydro-1,5,3-benzodithiazepine Chemical compound Clc1cccc(c1)N1CSc2ccccc2SC1 BEMHANGIWWUEJU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- MDDGQJVAUWXSCG-UHFFFAOYSA-N S1CNCSC2=C1C=CC=C2 Chemical compound S1CNCSC2=C1C=CC=C2 MDDGQJVAUWXSCG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000037427 ion transport Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000006452 multicomponent reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/36—Seven-membered rings
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- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Предлагаемое изобретение относится к области органической химии, конкретно к способу получения 3-(o,м,n-галогенфенил)-3,4-дигидро-2Н-бензо[f][1,5,3]дитиазепинов общей формулы (1):The present invention relates to the field of organic chemistry, specifically to a method for producing 3- (o, m, n-halogenophenyl) -3,4-dihydro-2H-benzo [f] [1,5,3] dithiazepines of the general formula (1):
Циклические азот-, кислород- и серосодержащие макроциклы перспективны в качестве селективных лигандов (Eds. Y. Inoue, G.W. Gokel. Cation Binding by Macrocycles. Marcel Dekker. New York. 1990; R.M. Izatt, K. Pawlak, J.S. Bradshaw, R.L. Braening. Chem. Rev., 1991, 91, 1721 p) для экстракции и разделения катионов металлов (А.Т. Yordanov, D.M. Roimdhill. Coord. Chem. Rev., 1998, 170, 93 p; K. Gloe, H. Graubaum, M. Wust, T. Rambusch, W. Seichter. Coord. Chem. Rev., 2001, 222, 103 p), для транспорта ионов через мембраны (P. Bushlmann, Е. Pretsch, Е. Bakker. Chem. Rev., 1998, 98, 1593 p), в фоточувствительных системах (В. Valeur, I. Leray. Coord. Chem. Rev., 2000, 205, 3 p), выступают в роли межфазных катализаторов, моделирующих ферментативную активность (М.С. Feiters. In comprehensive Supramolecular Chemistry. Pergamon Press. Oxford. 1996, 9, 267 p).Cyclic nitrogen, oxygen and sulfur-containing macrocycles are promising as selective ligands (Eds. Y. Inoue, GW Gokel. Cation Binding by Macrocycles. Marcel Dekker. New York. 1990; RM Izatt, K. Pawlak, JS Bradshaw, RL Braening. Chem. Rev., 1991, 91, 1721 p) for the extraction and separation of metal cations (A.T. Yordanov, DM Roimdhill. Coord. Chem. Rev., 1998, 170, 93 p; K. Gloe, H. Graubaum, M. Wust, T. Rambusch, W. Seichter. Coord. Chem. Rev., 2001, 222, 103 p), for ion transport through membranes (P. Bushlmann, E. Pretsch, E. Bakker. Chem. Rev., 1998, 98, 1593 p), in photosensitive systems (B. Valeur, I. Leray. Coord. Chem. Rev., 2000, 205, 3 p), they act as interfacial catalysts simulating the enzymatic activity (M.S. Feiters. In comprehensive Supramolecular Chemistry. Pergamon Press. Oxford. 1996, 9, 267 p).
Известен способ (К.К. Ellis, В. Wilke, Y. Zhang, S. Diver. A new method for the synthesis of imidazolidinone- and benzimidazalone-containing[2.2]cyclophanes. Organic Letters, 2000, 2, 24, 3785-3788) получения гетероциклофанов (2) взаимодействием производных бензо-1,4-диметантиола с 1,3-бис(метоксиметил)имидазолидин-2-оном при кипячении в хлористом метилене в присутствии 1% трифторуксусной кислоты с выходом 40%.The known method (K.K. Ellis, W. Wilke, Y. Zhang, S. Diver. A new method for the synthesis of imidazolidinone- and benzimidazalone-containing [2.2] cyclophanes. Organic Letters, 2000, 2, 24, 3785- 3788) for the preparation of heterocyclophanes (2) by the interaction of benzo-1,4-dimethanethiol derivatives with 1,3-bis (methoxymethyl) imidazolidin-2-one upon boiling in methylene chloride in the presence of 1% trifluoroacetic acid with a yield of 40%.
Известным способом не могут быть получены 3-(o,м,n-галогенфенил)-3,4-дигидро-2Н-бензо[f][1,5,3]дитиазепины формулы (1).In a known manner, 3- (o, m, n-halogenophenyl) -3,4-dihydro-2H-benzo [f] [1,5,3] dithiazepines of the formula (1) cannot be obtained.
Известен способ (G.R. Khabibullina, V.R. Akhmetova, M.F. Abdullin, T.V. Tyumkina, L.M. Khalilov, A.G. Ibragimov. Multicomponent reactions of amino alcohols with CH2O and dithiols in the synthesis of 1,3,5-dithiazepanes and macroheterocycles. Tetrahedron, 2014, 70, 3502-3509) получения 2-[18,32-бис(2-гидроксиэтил)-11,25,39-триокса-2,6,16,20,30,34-гексатиа-4,18,32-триазагептацикло[38.2.2.27,10.212,15.221,24.226,29.235,38]тетрапентаконта-1(43),7(54),8,10(53),12(52),13,15(51),21(50),22,24(49),26(48),27,29(47),35(46),36,38(45),40,41-октадекаен-4-ил]-1-этанола (3) с выходом 62% в смеси с побочным макрогетероциклом (4) циклоконденсацией моноэтаноламина с CH2O и 4,4'-димеркаптодифенилоксидом (мольное соотношение 1:2:1) в растворе хлороформа за 4 ч.The known method (GR Khabibullina, VR Akhmetova, MF Abdullin, TV Tyumkina, LM Khalilov, AG Ibragimov. Multicomponent reactions of amino alcohols with CH 2 O and dithiols in the synthesis of 1,3,5-dithiazepanes and macroheterocycles. Tetrahedron, 2014, 70, 3502-3509) for the preparation of 2- [18,32-bis (2-hydroxyethyl) -11,25,39-trioxa-2,6,16,20,30,34-hexathia-4,18,32-triazageptacyclo [38.2.2.2 7.10 .2 12.15 .2 21.24 .2 26.29 .2 35.38 ] tetrapentactont-1 (43), 7 (54), 8.10 (53), 12 (52 ), 13.15 (51), 21 (50), 22.24 (49), 26 (48), 27.29 (47), 35 (46), 36.38 (45), 40.41-octadecaen -4-yl] -1-ethanol (3) with a yield of 62% in a mixture with side macroheterocycle (4) cyclocondensation of monoethanolamine with CH 2 O and 4,4'-dimercaptodiphenyl oxide (molar ratio 1: 2: 1) in a solution of chloroform 4 hours
Известным способом не могут быть получены 3-(o,м,n-галогенфенил)-3,4-дигидро-2Н-бензо[f][1,5,3]дитиазепины формулы (1).In a known manner, 3- (o, m, n-halogenophenyl) -3,4-dihydro-2H-benzo [f] [1,5,3] dithiazepines of the formula (1) cannot be obtained.
Таким образом, в литературе отсутствуют сведения о селективном получении 3-(o,м,n-галогенфенил)-3,4-дигидро-2Н-бензо[f][1,5,3]дитиазепинов формулы (1).Thus, in the literature there is no information on the selective preparation of 3- (o, m, n-halogenophenyl) -3,4-dihydro-2H-benzo [f] [1,5,3] dithiazepines of the formula (1).
Предлагается новый способ получения 3-(o,м,n-галогенфенил)-3,4-дигидро-2Н-бензо[f][1,5,3]дитиазепинов общей формулы (1).A new method is proposed for the preparation of 3- (o, m, n-halogenophenyl) -3,4-dihydro-2H-benzo [f] [1,5,3] dithiazepines of general formula (1).
Сущность способа заключается во взаимодействии N,N-бис(метоксиметил)-N-(o,м,n-галогенфенил)(o,м,n-хлорфенил, o,м,n-бромфенил, o,м,n-фторфенил)амина с бензол-1,2-дитиолом в присутствии катализатора кристаллогидрата азотнокислого самария Sm(NO3)3*6H2O, взятыми в мольном соотношении N,N-бис(метоксиметил)-N-(o,м,n-галогенфенил)амин : бензол-1,2-дитиол : Sm(NO3)3*6H2O = 1:1:(0.03-0.07), предпочтительно 1:1:0.05, при комнатной (~20°C) температуре и атмосферном давлении в этиловом эфире уксусной кислоты в качестве растворителя в течение 6-8 ч, предпочтительно 7 ч. Выход соответствующих 3-(o,м,n-галогенфенил)-3,4-дигидро-2Н-бензо[f][1,5,3] дитиазепинов общей формулы (1) составляет 71-84%. Реакция протекает по схеме:The essence of the method consists in the interaction of N, N-bis (methoxymethyl) -N- (o, m, n-halogenophenyl) (o, m, n-chlorophenyl, o, m, n-bromophenyl, o, m, n-fluorophenyl) amine with benzene-1,2-dithiol in the presence of a samarium nitrate crystalline hydrate catalyst Sm (NO 3 ) 3 * 6H 2 O, taken in a molar ratio of N, N-bis (methoxymethyl) -N- (o, m, n-halogenophenyl) amine: benzene-1,2-dithiol: Sm (NO 3 ) 3 * 6H 2 O = 1: 1: (0.03-0.07), preferably 1: 1: 0.05, at room temperature (~ 20 ° C) and atmospheric pressure in ethyl acetate, as solvent for 6-8 hours, preferably 7 hours. Yield 3- (o, m, n-halophenyl) -3,4-dihydro-2H-benzo [f] [1,5,3] ditiazepinov general formula (1) is 71-84%. The reaction proceeds according to the scheme:
3-(o,м,n-Галогенфенил)-3,4-дигидро-2Н-бензо[f][1,5,3]дитиазепины общей формулы (1) образуются только лишь с участием N,N-бис(метоксиметил)-N-(o,м,n-галогенфенил)аминов и бензол-1,2-дитиола, взятых в стехиометрических количествах. При другом соотношении исходных реагентов снижается выход целевых продуктов (1). Без катализатора реакция не идет.3- (o, m, n-halogenophenyl) -3,4-dihydro-2H-benzo [f] [1,5,3] dithiazepines of the general formula (1) are formed only with the participation of N, N-bis (methoxymethyl) -N- (o, m, n-halogenophenyl) amines and benzene-1,2-dithiol, taken in stoichiometric quantities. With a different ratio of the starting reagents, the yield of the target products decreases (1). Without a catalyst, the reaction does not go.
Проведение указанной реакции в присутствии катализатора Sm(NO3)3*6H2O больше 7 мол. % в расчете на исходный N,N-бис(метоксиметил)-N-(o,м,n-галогенфенил)амин не приводит к существенному увеличению выхода целевого продукта (1). Использование катализатора Sm(NO3)3*6H2O менее 3 мол. % снижает выход (1), что связано, возможно, со снижением каталитически активных центров в реакционной массе. Реакции проводили при температуре 20°C. При температуре выше 20°C (например, 60°C) увеличиваются энергозатраты, а при температуре ниже 20°C (например, 0°C) снижается скорость реакции. Опыты проводили в этиловом эфире уксусной кислоты, т.к. в нем хорошо растворяются исходные реагенты и целевые продукты.Carrying out the specified reaction in the presence of a catalyst Sm (NO 3 ) 3 * 6H 2 O more than 7 mol. % based on the initial N, N-bis (methoxymethyl) -N- (o, m, n-halogenophenyl) amine does not significantly increase the yield of the target product (1). The use of the catalyst Sm (NO 3 ) 3 * 6H 2 O less than 3 mol. % reduces the yield (1), which is possibly associated with a decrease in catalytically active centers in the reaction mass. Reactions were carried out at a temperature of 20 ° C. At temperatures above 20 ° C (for example, 60 ° C), energy costs increase, and at temperatures below 20 ° C (for example, 0 ° C) the reaction rate decreases. The experiments were carried out in ethyl acetate, because source reagents and target products dissolve well in it.
Существенные отличия предлагаемого способа:Significant differences of the proposed method:
В предлагаемом способе в реакцию с N,N-бис(метоксиметил)-N-(o,м,n-галогенфенил)аминами вовлекается бензол-1,2-дитиол в присутствии каталитических количеств Sm(NO3)3*6H2O. Реакция идет с селективным образованием 3-(o,м,n-галогенфенил)-3,4-дигидро-2Н-бензо[f][1,5,3]дитиазепинов формулы (1).In the proposed method, benzene-1,2-dithiol is involved in the reaction with N, N-bis (methoxymethyl) -N- (o, m, n-halogenophenyl) amines in the presence of catalytic amounts of Sm (NO 3 ) 3 * 6H 2 O. The reaction proceeds with the selective formation of 3- (o, m, n-halogenophenyl) -3,4-dihydro-2H-benzo [f] [1,5,3] dithiazepines of the formula (1).
В известном способе макроцикл формулы (3) получают в смеси с побочным гетероциклом (4) трехкомпонентной конденсацией аминоэтанола с формальдегидом и 4,4-димеркаптодифенилоксидом.In the known method, a macrocycle of formula (3) is prepared in a mixture with a side heterocycle (4) by three-component condensation of aminoethanol with formaldehyde and 4,4-dimercaptodiphenyl oxide.
Предлагаемый способ обладает следующими преимуществами:The proposed method has the following advantages:
Способ позволяет получать с высокой селективностью и выходами 3-(o,м,n-галогенфенил)-3,4-дигидро-2Н-бензо[f][1,5,3] дитиазепины формулы (1).The method allows to obtain with high selectivity and yields of 3- (o, m, n-halogenophenyl) -3,4-dihydro-2H-benzo [f] [1,5,3] dithiazepines of the formula (1).
Способ поясняется следующими примерами:The method is illustrated by the following examples:
ПРИМЕР 1. В сосуд Шленка, установленный на магнитной мешалке, помещают 0.21 г (1 ммоль) N,N-бис(метоксиметил)-N-(n-хлорфенил)амина и 0.14 г (1 ммоль) бензол-1,2-дитиола, 5 мл этилового эфира уксусной кислоты, 0.02 г [5 мол. % в расчете на N,N-бис(метоксиметил)-N-n-хлорфениламин] Sm(NO3)3*6H2O, перемешивают при комнатной (~20°C) температуре 7 ч, выделяют 3-(n-хлорфенил)-3,4-дигидро-2Н-бензо[f][1,5,3]дитиазепин (1) с выходом 73%.EXAMPLE 1. In a Schlenk vessel mounted on a magnetic stirrer, 0.21 g (1 mmol) of N, N-bis (methoxymethyl) -N- (n-chlorophenyl) amine and 0.14 g (1 mmol) of benzene-1,2-dithiol are placed , 5 ml of ethyl acetate, 0.02 g [5 mol. % based on N, N-bis (methoxymethyl) -Nn-chlorophenylamine] Sm (NO 3 ) 3 * 6H 2 O, stirred at room temperature (~ 20 ° C) for 7 hours, 3- (n-chlorophenyl) - is isolated 3,4-dihydro-2H-benzo [f] [1,5,3] dithiazepine (1) in 73% yield.
Другие примеры, подтверждающие способ, приведены в табл. 1.Other examples confirming the method are given in table. one.
Спектральные характеристики 3-(o-хлорфенил)-3,4-дигидро-2Н-бензо[f][1,5,3]дитиазепина:Spectral characteristics of 3- (o-chlorophenyl) -3,4-dihydro-2H-benzo [f] [1,5,3] dithiazepine:
Спектральные характеристики 3-(м-хлорфенил)-3,4-дигидро-2Н-бензо[f][1,5,3] дитиазепина:Spectral characteristics of 3- (m-chlorophenyl) -3,4-dihydro-2H-benzo [f] [1,5,3] dithiazepine:
Спектральные характеристики 3-(n-хлорфенил)-3,4-дигидро-2Н-бензо[f][1,5,3] дитиазепина:Spectral characteristics of 3- (n-chlorophenyl) -3,4-dihydro-2H-benzo [f] [1,5,3] dithiazepine:
Claims (3)
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2551668C1 (en) * | 2013-10-31 | 2015-05-27 | Федеральное государственное бюджетное учреждение науки нефтехимии и катализа РАН | Method of obtaining 3-(1-adamantyl)- and 3-[1-(1-adamantyl)ethyl]-1,5,3-dithiazepinanes |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2551668C1 (en) * | 2013-10-31 | 2015-05-27 | Федеральное государственное бюджетное учреждение науки нефтехимии и катализа РАН | Method of obtaining 3-(1-adamantyl)- and 3-[1-(1-adamantyl)ethyl]-1,5,3-dithiazepinanes |
Non-Patent Citations (1)
| Title |
|---|
| G.R. Khabibullina, V.R. Akhmetova, M.F. Abdullin, T.V. Tyumkina, L.M. Khalilov, A.G. Ibragimov. Multicomponent reactions of amino alcohols with CH 2 O and dithiols in the synthesis of 1,3,5-dithiazepanes and macroheterocycles. Tetrahedron, 2014, 70, 3502-3509. * |
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| RU2016103462A (en) | 2017-08-07 |
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