Synthetic method of pyrazolo[3,4-b]thieno[2,3-e]pyridine derivative
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A 4-b, pyrazolo technology, applied in the field of organic synthesis, can solve the problem of few synthesis methods of pyridine derivatives
Inactive Publication Date: 2012-09-12
XUZHOU NORMAL UNIVERSITY
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But the synthetic method research of pyrazolo[3,4-b]thieno[2,3-e]pyridine derivatives is less, only a small amount of reports (Drizin, I.; Altenbach, R.J.; Buckner, S.A.; Whiteaker, K.L.; Scott, V.E.; Darbyshire, J.F.; Jayanti, V.; Henry, R.F.; Coghlan, M.J.; Gopalakrishnan, M.; Carroll, W.A. Bioorg. Med. Chem.
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Embodiment 1
[0008] 3-Methyl-1-phenyl-4-phenyl-4,6,7,8-tetrahydropyrazolo[3,4-b]thieno[2,3-e]pyridine-5,5- Preparation of dioxide (4a): 1 mmol of benzaldehyde (0.11 g), 1 mmol of 1-phenyl-3-methyl-5-aminopyrazole (0.17 g) and 1 mmol in a mortar Millimoles of 3-oxosulfolane (0.13g) was reacted at 85°C for 13 hours, followed by TLC monitoring. After the reaction, the solid product obtained by the reaction was transferred to a round-bottomed flask with a small amount of ethanol, and recrystallized with ethanol and DMF. The corresponding 3-methyl-1-phenyl-4-phenyl-4,6,7,8-tetrahydropyrazolo[3,4-b]thieno[2,3-e]pyridine-5 , 5-dioxide (0.31 g, 82% yield). This product is colorless powder, melting point: 243-245℃.
[0009] The reaction raw materials of embodiment 1-8, reaction time and productive rate are shown in Table 1.
[0010] The reaction raw material of table 1 embodiment 1-8, reaction condition and productive rate
[0011]
[0012] It can be seen from the table that the method of th...
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Abstract
The invention relates to synthesis of a pyrazolo[3,4-b]thieno[2,3-e]pyridine derivative, in particular to synthesis of pyrazolo[3,4-b]thieno[2,3-e]pyridine. The pyrazolo[3,4-b]thieno[2,3-e]pyridine derivative is generated by taking aromatic aldehyde, 1-phenyl-3-methyl-5-aminopyrazole and 3-oxosulfolane as raw materials in one step under a solvent-free and catalyst-free condition with a three-component one-pot process. According to the method, a synthesis process has a simple and convenient route, conditions are mild, and the total yield is over 78 percent.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a synthesis method of pyrazolo[3,4-b]thieno[2,3-e]pyridine derivatives. Background technique [0002] Pyrazolo[2,3-e]pyridine derivatives have important physiological and pharmacological activities, such as parasiticide, LPA receptor antagonist, antibacterial, CDK5-p25 kinase inhibitor, ALK kinase inhibitor (Berger, M. ; Kern, C.; Eck, M.; Schroeder, J. WO Patent 2, 012, 041, 873, 2012, Chem. Abstr. 2012, 156, 505360; Schiemann, K.; Staehle, M.; Wienke, D .WO Patent 2, 012, 028, 243, 2012, Chem.Abstr.2012, 156, 390167; Frolova, L.V.; Malik, I.; Uglinskii, P.Y.; Rogelj, S.; Komienko, A.; Magedov, I.V. Tetrahedron Lett. 2011, 52(49), 6643-6645; Siu, T.; Dinsmore, C.; Kumarasinghe, S.E. WO Patent 2, 011, 049, 722, 2011, Chem. K.; Rabot, R.; Kaloun, E.B.; Mayer, P.; Marchand, A.; Rahier, N.; Abstr. 2011, 154, 513388.). Therefore, such compounds have always been a focus of ...
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