CN110183397A - Bis cyclopentadienyl zirconium dichloride is catalyzed the method for preparing 1,5- benzo thiazides compounds - Google Patents
Bis cyclopentadienyl zirconium dichloride is catalyzed the method for preparing 1,5- benzo thiazides compounds Download PDFInfo
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- CN110183397A CN110183397A CN201910547061.2A CN201910547061A CN110183397A CN 110183397 A CN110183397 A CN 110183397A CN 201910547061 A CN201910547061 A CN 201910547061A CN 110183397 A CN110183397 A CN 110183397A
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- zirconium dichloride
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- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
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Abstract
The invention discloses a kind of bis cyclopentadienyl zirconium dichloride catalysis preparations 1, the method of 5- benzo thiazides compounds, this method is using 3- crotonylene -one class compound and adjacent aminobenzene sulfur alcohol compound as raw material, using bis cyclopentadienyl zirconium dichloride as catalyst, under the promotion of the ligands such as L-phenylalanine, 3- nitrophthalic acid, 2- aminobenzenesulfonic acid, it can efficient, high yield preparation 1,5- benzo thiazides compounds.Used catalyst dosage of the present invention is few, it is inexpensive, nontoxic, to air-stable, reaction condition is mild, the time is short, it is easy to operate, Atom economy is high, only product need to be passed through simple column chromatography for separation after reaction, can be obtained 1,5- benzo thiazides compounds, new inexpensive, efficient approach is opened for the preparation of 1,5- benzo thiazides compounds, is had broad application prospects.
Description
Technical field
The invention belongs to the synthesis technical fields of 1,5- benzo thiazides compounds, and in particular to a kind of bis cyclopentadienyl zirconium dichloride is urged
Change 3- crotonylene -one class compound and adjacent aminobenzene sulfur alcohol compound reaction, efficiently prepares 1,5- benzo thiazides compounds
Method.
Background technique
1,5- benzothiazine skeleton is widely present in natural products, has been confirmed as the pharmacophoric group of a multiple-effect,
Derivative includes inverase and anticancer drug, angiotensin converting enzyme inhibitors, antibiotic and antifungal compound, calcium
Heregulin antagonist and Ca2+Retarding agent etc..Further, since many 1,5- benzo thiazides compounds have antimycotic, antibacterial,
Anti-inflammatory, analgesia and anti-convulsant activity, are of great significance in drug and organic synthesis.
And relative to stable five-membered ring, six-membered ring structure, researchers are to the appendicular research on heptatomic ring at present
At least, therefore specifically for the synthesis of the diversity of 1, the 5- benzo thiazides compounds of heptatomic ring lack very much.It develops more multistable
Fixed, cheap, efficient, mild condition catalysis process, is of great significance to the preparation of 1,5- benzo thiazides compounds.
Summary of the invention
The object of the present invention is to provide it is a kind of it is easy to operate, reaction condition is mild, efficiently prepare 2,4- diphenyl -1,5- benzene
And the method for thiazine derivative.
For above-mentioned purpose, the technical scheme adopted by the invention is that: by the -one class compound of 3- crotonylene shown in Formulas I and
The sulfur alcohol compound of neighbour's aminobenzene shown in Formula II is added in organic solvent, and bis cyclopentadienyl zirconium dichloride and ligand is added, in room temperature~60
It is stirred to react at DEG C 1~12 hour, isolates and purifies product, obtain formula III depicted 1,5- benzo thiazides compounds.
R in formula1And R2It is independent to represent aryl or substituted aryl, specifically such as: phenyl, C1~C4Alkyl-substituted phenyl,
C1~C4Alkoxy substituted phenyl, halogenophenyl, trifluoromethyl substituted-phenyl, nitro substituted-phenyl, thienyl etc.；R3、R4、R5、
R6It is independent to represent H, fluorine, chlorine, bromine, C1~C4Alkyl, C1~C4Any one in alkoxy.
Above-mentioned organic solvent is methylene chloride, tetrahydrofuran, any one in toluene, preferably methylene chloride.
Above-mentioned ligand is L-phenylalanine, 3- nitrophthalic acid, any one in 2- aminobenzenesulfonic acid, preferably L-
Phenylalanine.
In above-mentioned preparation method, the preferably described 3- crotonylene -one class compound rubs with adjacent aminobenzene sulfur alcohol compound
You are than being 1:1~1.5.
In above-mentioned preparation method, the additional amount 3- crotonylene -one class compound mole of the preferably described bis cyclopentadienyl zirconium dichloride
1%~6%.
In above-mentioned preparation method, the additional amount of the preferably described ligand be 3- crotonylene -one class compound mole 2%~
12%.
In above-mentioned preparation method, further preferably it is stirred to react at 40~50 DEG C 4~6 hours.
The present invention is using bis cyclopentadienyl zirconium dichloride as catalyst, with L-phenylalanine, 3- nitrophthalic acid, 2- aminobenzenesulfonic acid
It, can efficient catalytic 3- crotonylene -one class compound and adjacent aminobenzene sulfur alcohol compound reaction, preparation 1,5- for catalyst ligand
Benzo thiazides compounds.Used catalyst dosage of the present invention is few, it is inexpensive, nontoxic, to air-stable, reaction condition is mild, when
Between short, nontoxic solvent, it is easy to operate, after reaction only need to by product pass through simple column chromatography for separation, can be obtained has
1, the 5- benzo thiazides compounds of extensive bioactivity and medical value, are opened for the preparation of 1,5- benzo thiazides compounds
The approach for having warded off new low cost and green high-efficient, has broad application prospects.
Specific embodiment
Below with reference to embodiment, the present invention is described in more detail, but protection scope of the present invention is not limited only to these realities
Apply example.
Embodiment 1
The following 2,4- diphenyl -1,5- benzothiazine of preparation structure formula
The adjacent ammonia of 0.103g (0.5mmol) 1,4- diphenyl -3- crotonylene -one, 65 μ L (0.6mmol) is added into reaction tube
Base benzenethiol, 0.0074g (0.025mmol) bis cyclopentadienyl zirconium dichloride, 0.0083g (0.05mmol) L-phenylalanine, 1mL dichloromethane
Alkane, reflux is stirred to react 5h at 50 DEG C, stops reaction, and rotary evaporation removes methylene chloride, and with silica gel post separation, (eluant, eluent is
Petroleum ether and methylene chloride volume are than the mixed liquor for 2:1), 2,4- diphenyl -1,5- benzothiazine is obtained, yield is
97%, the spectral data of product are as follows:1H NMR(400MHz,CDCl3) δ 8.03 (dd, J=6.5,2.9Hz, 2H), 7.82 (d, J=
7.3Hz, 2H), 7.48-7.32 (m, 9H), 7.15 (t, J=7.6Hz, 1H), 6.85 (s, 1H)；13C NMR(101MHz,CDCl3)
δ165.83,150.33,150.07,139.32,138.58,132.82,130.91,129.65,129.41,128.69,
128.61,128.15,127.92,127.56,126.69,126.41,124.52.
Comparative example 1
In embodiment 1, the tyrosine replacement of L-phenylalanine equimolar amounts used, other steps and embodiment 1
It is identical, obtain 2,4- diphenyl -1,5- benzothiazine, yield 37%.
Comparative example 2
In embodiment 1, the 5-sulphosalicylic acid replacement of L-phenylalanine equimolar amounts used, other steps and reality
It is identical to apply example 1, obtains 2,4- diphenyl -1,5- benzothiazine, yield 35%.
Embodiment 2
The following 2- of preparation structure formula (4- chlorphenyl) -4- phenyl -1,5- benzothiazine
In the present embodiment, used in equimolar 1- (4- chlorphenyl) -4- phenyl -3- crotonylene -one alternative embodiment 1
Isosorbide-5-Nitrae-diphenyl -3- crotonylene -one, other steps are same as Example 1, obtain 2- (4- chlorphenyl) -4- phenyl -1,5- benzo
Thiazine, yield 94%, the spectral data of product are as follows:1H NMR(400MHz,CDCl3) δ 7.88 (d, J=8.3Hz, 2H),
7.77-7.70 (m, 2H), 7.35 (dd, J=7.9,4.9Hz, 3H), 7.29 (dd, J=6.9,4.9Hz, 5H), 7.10 (dt, J=
8.4,4.3Hz,1H),6.73(s,1H)；13C NMR(101MHz,CDCl3)δ165.92,151.90,151.48,139.80,
139.14,138.42,134.21,131.12,130.82,130.59,130.17,130.08,129.32,128.91,128.28,
127.77,125.29.
Embodiment 3
The following 2- of preparation structure formula (4- bromophenyl) -4- phenyl -1,5- benzothiazine
In the present embodiment, used in equimolar 1- (4- bromophenyl) -4- phenyl -3- crotonylene -one alternative embodiment 1
Isosorbide-5-Nitrae-diphenyl -3- crotonylene -one, other steps are same as Example 1, obtain 2- (4- bromophenyl) -4- phenyl -1,5- benzene
And thiazine, yield 91%, the spectral data of product are as follows:1H NMR(400MHz,CDCl3) δ 7.80 (d, J=8.6Hz, 2H),
7.74-7.69 (m, 2H), 7.49 (d, J=8.5Hz, 2H), 7.35 (d, J=7.7Hz, 1H), 7.32-7.24 (m, 5H), 7.09
(dt, J=8.3,4.4Hz, 1H), 6.71 (s, 1H)；13C NMR(101MHz,CDCl3)δ166.02,151.94,151.48,
139.79,139.58,134.22,133.13,131.13,130.83,130.81,130.09,129.31,128.91,128.31,
127.76,126.92,125.22.
Embodiment 4
The following 2- of preparation structure formula (4- fluorophenyl) -4- phenyl -1,5- benzothiazine
In the present embodiment, used in equimolar 1- (4- fluorophenyl) -4- phenyl -3- crotonylene -one alternative embodiment 1
Isosorbide-5-Nitrae-diphenyl -3- crotonylene -one, other steps are same as Example 1, obtain 2- (4- fluorophenyl) -4- phenyl -1,5- benzene
And thiazine, yield 97%, the spectral data of product are as follows:1H NMR(400MHz,CDCl3) δ 7.95 (dd, J=8.7,
5.6Hz, 2H), 7.77-7.70 (m, 2H), 7.36 (d, J=7.8Hz, 1H), 7.34-7.26 (m, 5H), 7.08 (qd, J=8.5,
3.0Hz,3H),6.75(s,1H)；13C NMR(101MHz,CDCl3)δ164.76,163.42,162.26,149.21,149.06,
137.37,134.45,134.42,131.71,128.93,128.85,128.60,128.32,127.59,126.87,126.42,
125.64,125.24,122.97,114.57,114.36.
Embodiment 5
The following 2- of preparation structure formula (4- aminomethyl phenyl) -4- phenyl -1,5- benzothiazine
In the present embodiment, with institute in equimolar 1- (4- aminomethyl phenyl) -4- phenyl -3- crotonylene -one alternative embodiment 1
Isosorbide-5-Nitrae-diphenyl-3- crotonylene -one, other steps are same as Example 1, obtain 2- (4- aminomethyl phenyl) phenyl-1-4-,
5- benzothiazine, yield 86%, the spectral data of product are as follows:1H NMR(400MHz,CDCl3) δ 7.99 (d, J=8.1Hz,
2H), 7.92-7.85 (m, 2H), 7.51 (d, J=7.8Hz, 1H), 7.44 (q, J=5.3Hz, 5H), 7.33 (d, J=8.0Hz,
2H),7.25-7.19(m,1H),6.93(s,1H),2.47(s,3H)；13C NMR(101MHz,CDCl3)δ167.04,151.79,
151.16,142.60,140.07,138.05,134.14,130.92,130.71,130.68,130.04,129.58,129.23,
128.91,127.83,127.72,125.98,22.95.
Embodiment 6
The following 2- of preparation structure formula (4- methoxyphenyl) -4- phenyl -1,5- benzothiazine
In the present embodiment, in equimolar 1- (4- methoxyphenyl) -4- phenyl -3- crotonylene -one alternative embodiment 1
Isosorbide-5-Nitrae used-diphenyl -3- crotonylene -one, other steps are same as Example 1, obtain 2- (4- methoxyphenyl) -4- benzene
Base -1,5- benzothiazine, yield 71%, the spectral data of product are as follows:1H NMR(400MHz,CDCl3) δ 7.92 (d, J=
8.5Hz, 2H), 7.78-7.72 (m, 2H), 7.37 (d, J=7.8Hz, 1H), 7.29 (q, J=5.2,3.5Hz, 5H), 7.11-
7.04 (m, 1H), 6.90 (d, J=8.5Hz, 2H), 6.78 (s, 1H), 3.78 (s, 3H)；13C NMR(101MHz,CDCl3)δ
163.90,160.86,149.35,148.53,137.62,131.64,130.96,128.43,128.23,127.55,127.03,
126.42,125.19,125.16,123.39,112.82,54.39.
Embodiment 7
Following 2- phenyl -4- (4- the fluorophenyl) -1,5- benzothiazine of preparation structure formula
In the present embodiment, used in equimolar 1- phenyl -4- (4- fluorophenyl) -3- crotonylene -one alternative embodiment 1
Isosorbide-5-Nitrae-diphenyl -3- crotonylene -one, other steps are same as Example 1, obtain 2- phenyl -4- (4- fluorophenyl) -1,5- benzene
And thiazine, yield 98%, the spectral data of product are as follows:1H NMR(400MHz,CDCl3) δ 7.93 (dd, J=6.6,
3.0Hz, 2H), 7.51 (d, J=7.9Hz, 1H), 7.48-7.43 (m, 1H), 7.39 (d, J=2.1Hz, 2H), 7.39-7.34
(m, 2H), 7.29 (dd, J=6.4,3.2Hz, 2H), 7.27-7.21 (m, 1H), 7.10 (ddd, J=8.3,6.2,2.7Hz,
1H), 6.97 (td, J=8.2,2.1Hz, 1H), 6.78 (s, 1H)；13C NMR(101MHz,CDCl3)δ165.44,164.09,
161.63,150.12,148.38,148.36,140.80,140.73,139.07,132.73,130.98,130.19,130.11,
129.50,128.61,127.82,127.72,126.80,126.44,125.29,123.12,123.09,116.56,116.35,
114.64,114.41.
Embodiment 8
Following 2- phenyl -4- (2- the thienyl) -1,5- benzothiazine of preparation structure formula
In the present embodiment, used in equimolar 1- phenyl -4- (2- thienyl) -3- crotonylene -one alternative embodiment 1
Isosorbide-5-Nitrae-diphenyl -3- crotonylene -one, other steps are same as Example 1, obtain 2- phenyl -4- (2- thienyl) -1,5- benzene
And thiazine, yield 87%, the spectral data of product are as follows:1H NMR(400MHz,CDCl3) δ 7.90 (dd, J=6.6,
2.9Hz, 2H), 7.53 (d, J=3.7Hz, 1H), 7.40-7.34 (m, 3H), 7.34-7.25 (m, 3H), 7.19 (d, J=
5.1Hz, 1H), 7.06 (td, J=7.7,7.2,2.4Hz, 1H), 6.92 (t, J=4.4Hz, 1H), 6.75 (s, 1H)；13C NMR
(101MHz,CDCl3)δ165.47,150.29,143.11,142.32,139.35,132.77,130.88,129.50,
128.56,128.24,128.21,128.00,127.94,127.36,126.71,126.41,121.43.
Embodiment 9
In the present embodiment, the L-phenylalanine used in equimolar 2- aminobenzenesulfonic acid alternative embodiment 1, other steps
It is same as Example 1, obtain 2,4- phenyl -1,5- benzothiazine, yield 71%.
Embodiment 10
In the present embodiment, the L-phenylalanine used in equimolar 3- nitrophthalic acid alternative embodiment 1 is other
Step is same as Example 1, obtains 2,4- phenyl -1,5- benzothiazine, yield 68%.
Embodiment 11
In the present embodiment, the methylene chloride used in isometric tetrahydrofuran alternative embodiment 1, other steps and implement
Example 1 is identical, obtains 2,4- phenyl -1,5- benzothiazine, yield 65%.
Embodiment 12
In the present embodiment, the methylene chloride used in isometric toluene alternative embodiment 1, other steps and embodiment 1
It is identical, obtain 2,4- phenyl -1,5- benzothiazine, yield 68%.
Claims (8)
1. a kind of method of bis cyclopentadienyl zirconium dichloride catalysis preparation 1,5- benzo thiazides compounds, it is characterised in that: by 3- shown in Formulas I
Neighbour's aminobenzene sulfur alcohol compound shown in crotonylene -one class compound and Formula II is added in organic solvent, and two cyclopentadienyl of dichloro is added
Zirconium and ligand are stirred to react 1~12 hour at room temperature~60 DEG C, isolate and purify product, obtain formula III depicted 1,5- benzo thiophene
Piperazine class compound；
R in formula1And R2It is independent to represent aryl or substituted aryl；R3、R4、R5、R6It is independent represent H, fluorine, chlorine, bromine,
C1~C4Alkyl, C1~C4Any one in alkoxy；
Above-mentioned organic solvent is methylene chloride, tetrahydrofuran, any one in toluene；
Above-mentioned ligand is L-phenylalanine, 3- nitrophthalic acid, any one in 2- aminobenzenesulfonic acid.
2. the method for bis cyclopentadienyl zirconium dichloride catalysis preparation 1,5- benzo thiazides compounds according to claim 1, feature
It is: the R1And R2It is independent to represent phenyl, C1~C4Alkyl-substituted phenyl, C1~C4Alkoxy substituted phenyl, halogen
For any one in phenyl, trifluoromethyl substituted-phenyl, nitro substituted-phenyl, thienyl.
3. the method for bis cyclopentadienyl zirconium dichloride catalysis preparation 1,5- benzo thiazides compounds according to claim 1 or 2, special
Sign is: the organic solvent is methylene chloride.
4. according to claim 1 or the bis cyclopentadienyl zirconium dichloride is catalyzed the method for preparing 1,5- benzo thiazides compounds, special
Sign is: the ligand is L-phenylalanine.
5. the method for bis cyclopentadienyl zirconium dichloride catalysis preparation 1,5- benzo thiazides compounds according to claim 1 or 2, special
Sign is: the molar ratio of the 3- crotonylene -one class compound and adjacent aminobenzene sulfur alcohol compound is 1:1~1.5.
6. the method for bis cyclopentadienyl zirconium dichloride catalysis preparation 1,5- benzo thiazides compounds according to claim 1 or 2, special
Sign is: the additional amount of the bis cyclopentadienyl zirconium dichloride is the 1%~6% of 3- crotonylene -one class compound mole.
7. the method for bis cyclopentadienyl zirconium dichloride catalysis preparation 1,5- benzo thiazides compounds according to claim 1 or 2, special
Sign is: the additional amount of the ligand is the 2%~12% of 3- crotonylene -one class compound mole.
8. the method for bis cyclopentadienyl zirconium dichloride catalysis preparation 1,5- benzo thiazides compounds according to claim 1 or 2, special
Sign is: being stirred to react at 40~50 DEG C 4~6 hours.
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2019
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3075968A (en) * | 1961-09-18 | 1963-01-29 | Olin Mathieson | Benzothiazepines |
| GB1317475A (en) * | 1969-06-11 | 1973-05-16 | Boehringer Sohn Ingelheim | Benzodiazepines the preparation thereof and compositions containing the same |
| AU2012251921A1 (en) * | 2008-06-20 | 2012-12-06 | Astrazeneca Ab | Dibenzothiazepine derivatives and use thereof |
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| GEMMA CABARROCAS ET AL.: "Synthesis of novel optically pure quinolyl-β-amino alcohol derivatives from 2-amino thiophenol and chiral α-acetylenic ketones and their IBX-mediated oxidative cleavage to N-Boc quinolyl carboxamides", 《TETRAHEDRON: ASYMMETRY》 * |
| LINGAIAH NAGARAPU ET AL.: "BENZODIAZEPINE FUSED HETEROCYCLES IV : A CONVENIENT SYNTHESIS OF BENZO[b][1,5]THIAZEPINES USING MCM-41(H) ZEOLITE", 《HETEROCYCLIC COMMUNICATIOM》 * |
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