Naphtho-/anthra-pyrazole derivative and synthetic method thereof

An anthralopyrazole and derivative technology, applied in the field of pyrazole derivatives and their synthesis, can solve the problem of few synthesis methods of naphtho or anthrapyrazole derivatives, and achieve abundant synthesis methods, easy operation and mild conditions Effect

Inactive Publication Date: 2012-07-25
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, few synthetic methods of naphtho or anthracene pyrazole derivatives have been studied and reported

Method used

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  • Naphtho-/anthra-pyrazole derivative and synthetic method thereof
  • Naphtho-/anthra-pyrazole derivative and synthetic method thereof
  • Naphtho-/anthra-pyrazole derivative and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Oxydisilyloxabenzobicycloolefin 4 (0.5~1.5 eq), chlorinated arylhydrazone derivatives 5a (1.5~2.5 eq), triethylamine (3.5~4.5 eq), the cycloaddition product obtained is: 1-(4-methoxyphenyl)-3-methoxycarbonyl-6.7-oxodisilyl 3a,4,9,9a-tetrahydro-4,9-epoxynaphtho[2,3- d ]pyrazole ( 7a ), yield 89%, the structure of this compound is:

[0022]

[0023] Molecular formula: C 24 h 28 N 2 o 5 Si 2

[0024] Chinese name: 1-(4-methoxyphenyl)-3-methoxycarbonyl-6.7-oxodisilyl fused-3a,4,9,9a-tetrahydro-4,9-epoxynaphtho[ 2,3- d ] pyrazole

[0025] English name: 1-(4-methoxyphenyl)-3-methoxycarbonyl-6,7-oxadisilole fused-3a,4,9,9a-tetrahydro-4,9-epoxy-1 H -naphtho[2,3- d ]pyrazole

[0026] Molecular weight: 480.15

[0027] Appearance: yellow powder

[0028] H NMR (500 MHz, CDCl 3 ): δ 0.346 (s, 3H), δ 0.351 (s, 3H), 0.39 (s, 3H), 0.41 (s, 3H), 3.82 (s, 3H), 3.91 (d, J =9.0 Hz, 1H), 3.92 (s, 3H), 4.70 (d, J =9.0 Hz, 1H), 5.72 (s, 1H), 5.75 (s, 1H), 6.93 (d,J =9.0 ...

Embodiment 2

[0044] Oxydisilyloxabenzobicycloolefin 4 (0.5~1.5 eq), chlorinated arylhydrazone derivatives 5b (1.5~2.5 eq), triethylamine (3.5~4.5 eq), the cycloaddition product obtained is: 1-(4-methylphenyl)-3-methoxycarbonyl-6.7-oxodisilyl fused -3a,4,9,9a-tetrahydro-4,9-epoxynaphtho[2,3- d ]pyrazole ( 7b ), yield 78%, the structure of the compound is:

[0045]

[0046] Molecular formula: C 24 h 28 N 2 o 4 Si 2

[0047] Chinese name: 1-(4-methylphenyl)-3-methoxycarbonyl-6.7-oxodisilyl fused-3a,4,9,9a-tetrahydro-4,9-epoxynaphtho[2 ,3- d ] pyrazole

[0048] English name: 1-(4-methylphenyl)-3-methoxycarbonyl-6,7-oxadisilole fused-3a,4,9,9a-tetrahydro-4,9-epoxy-1 H -naphtho[2,3- d ]pyrazole

[0049] Molecular weight: 464.16

[0050] Appearance: yellow powder

[0051] H NMR (500 MHz, CDCl 3 ): δ 0.36 (s, 6H), 0.40 (s, 3H), 0.42 (s, 3H), 2.34 (s, 3H), 3.91 (d, J =9.5 Hz, 1H), 3.93 (s, 3H), 4.71 (d, J =9.5 Hz, 1H), 5.74 (s, 1H), 5.75 (s, 1H), 7.17-7.21 (m, 4H), 7.60 (d, J...

Embodiment 3

[0067] Oxydisilyloxabenzobicycloolefin 4 (0.5~1.5 eq), chlorophenylhydrazone derivatives 5c (1.5~2.5 eq), triethylamine (3.5~4.5 eq), the cycloaddition product obtained is: 1-phenyl-3-methoxycarbonyl-6.7-oxodisilyl fused-3a,4,9 ,9a-tetrahydro-4,9-epoxynaphtho[2,3- d ]pyrazole (7c ), yield 76%, the structure of the compound is:

[0068]

[0069] Molecular formula: C 23 h 26 N 2 o 4 Si 2

[0070] Chinese name: 1-phenyl-3-methoxycarbonyl-6.7-oxodisilyl fused-3a,4,9,9a-tetrahydro-4,9-epoxynaphtho[2,3- d ] pyrazole

[0071] English name: 1-phenyl-3-methoxycarbonyl-6,7-oxadisiole fused-3a,4,9,9a-tetrahydro-4,9-epoxy-1 H -naphtho[2,3- d ]pyrazole

[0072] Molecular weight: 450.14

[0073] Appearance: yellow powder

[0074] H NMR (500 MHz, CDCl 3 ): δ 0.359 (s, 3H), 0.360 (s, 3H), 0.40 (s, 3H), 0.42 (s, 3H), 3.92 (d, J =10 Hz, 1H), 3.93 (s, 3H), 4.72 (d, J =9.0 Hz, 1H), 5.75 (s, 1H), 5.76 (s, 1H), 7.03 (t, J =7.0 Hz, 1H), 7.28-7.31 (m, 2H), 7.36-7.40 (m, 2H), 7.61...

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Abstract

The invention relates to a naphtho- / anthra-pyrazole derivative and a synthetic method thereof. The structure of a compound is shown in the specifications, wherein X is OCH3, CH3, H, Cl or NO2. The naphtho- / anthra-pyrazole derivative is synthesized through twice cycloaddition reactions and a deoxygenization reaction, the requirement of an atom economy reaction is met, a brand new thought is provided for the establishment of a naphtho- / anthra-pyrazole framework, and a synthetic method of an organic heterocyclic compound is enriched. The synthetic method of the naphtho- / anthra-pyrazole derivative disclosed by the invention is not reported yet.

Description

technical field [0001] The invention relates to a pyrazole derivative and a synthesis method thereof, in particular to a naphtho or anthracene pyrazole derivative and a synthesis method thereof. Background technique [0002] It has been reported in the literature that benzopyrazole (or indazole) derivatives have a wide range of biological and pharmacological activities, not only as effective insecticides, herbicides, monomers of electroluminescent and heat-resistant materials, but also as anticancer , antiviral, antitumor and anti-inflammatory activities. Many natural compounds contain indazole rings, which are important mother nuclei. Naphthopyrazole derivatives can alleviate disease states such as tumor formation, metastasis, angiogenesis, vascular hyperpermeability, or endothelial cell proliferation. Anthrazopyrazole derivatives have therapeutic effects on leukemia, melanoma, sarcoma, and adenoma. [0003] At present, there are few researches and reports on the synthes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C07D231/54
Inventor 陈雅丽马旭燕张亚娟徐迪谢俊霖黄文成
Owner SHANGHAI UNIV
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