Phthalazine or benzo phthalazine derivative and preparation method thereof

A technology of benzophthalazine and derivatives, applied in the field of phthalazine or benzophthalazine derivatives and their preparation

Inactive Publication Date: 2014-10-15
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few studies on the synthesis of phthalazine or benzophthalazine derivatives reported in the literature

Method used

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  • Phthalazine or benzo phthalazine derivative and preparation method thereof
  • Phthalazine or benzo phthalazine derivative and preparation method thereof
  • Phthalazine or benzo phthalazine derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] 5a: Molecular formula: C 26 h 28 N 2 o 3 Si 2

[0022] Chinese name: 6,7-oxodisilyl-1,4-bis(4-methoxyphenyl)phthalazine

[0023] English name: 6,7-Oxadisilole-1,4-bis(4-methoxyphenyl) phthalazine

[0024] Molecular weight: 472.16

[0025] Appearance: yellow

[0026] H NMR (500 MHz, CDCl 3 ): δ 0.41 (s, 12H), 3.93 (s, 6H), 7.10-7.14 (m, 4H), 7.78 (d, J = 8.5 Hz, 4H), 8.31 (s, 2H) .

[0027] Carbon NMR (125 MHz, CDCl 3 ): δ 1.1, 55.5, 114.2, 125.7, 129.2, 131.6, 131.7, 152.0, 158.7, 160.7.

[0028] Maximum absorption wavelength: 323 nm (14.7×10 2 / M -1 cm) (CH 2 Cl 2 ).

[0029] Maximum emission wavelength: 482 nm (CH 2 Cl 2 ).

[0030] Quantum yield: 8.3% (CH 2 Cl 2 ).

[0031]

[0032] 6a: Molecular formula: C 28 h 34 N 2 o 4 Si 3

[0033] Chinese name: 6,7-Dioxytrisilyl-1,4-bis(4-methoxyphenyl)phthalazine

[0034] English name: 6,7-Dioxatrisilole-1,4-bis(4-methoxyphenyl) phthalazine

[0035] Molecular weight: 546.18

[0036]...

Embodiment 2

[0045]

[0046] 5b: Molecular formula: C 26 h 28 N 2 OSi 2

[0047] Chinese name: 6,7-oxodisilyl-1,4-bis(4-methylphenyl)phthalazine

[0048] English name: 6,7-Oxadisilole-1,4-bis(4-methylphenyl) phthalazine

[0049] Molecular weight: 440.17

[0050] Appearance: yellow

[0051] H NMR (500 MHz, CDCl 3 ): δ 0.42 (s, 12H), 2.51 (s, 6H), 7.43 (d, J = 8.0 Hz, 4H), 7.75 (d, J = 8.0 Hz, 4H), 8.33 (s, 2H) .

[0052] Carbon NMR (125 MHz, CDCl 3 ): δ 1.0, 21.5, 125.6, 129.1, 129.4, 130.2, 133.8, 139.3, 152.0, 159.2.

[0053] Maximum absorption wavelength: 309 nm (9.7×10 2 / M -1 cm) (CH 2 Cl 2 ).

[0054] Maximum emission wavelength: 435 nm (CH 2 Cl 2 ).

[0055] Quantum yield: 5.7% (CH 2 Cl 2 ).

[0056] 6b: Molecular formula: C 28 h 34 N 2 o 2 Si 3

[0057] Chinese name: 6,7-Dioxytrisilyl-1,4-bis(4-methylphenyl)phthalazine

[0058] English name: 6,7-Dioxatrisilole-1,4-bis(4-methylphenyl) phthalazine

[0059] 4-methylphenyl

[0060] Molecular weight: 5...

Embodiment 3

[0070]

[0071] 5c: Molecular formula: C 24 h 24 N 2 OSi 2

[0072] Chinese name: 6,7-oxodisilyl-1,4-diphenylphthalazine

[0073] English name: 6,7-Oxadisilole-1,4-diphenyl phthalazine

[0074] Molecular weight: 412.14

[0075] Appearance: yellow

[0076] H NMR (500 MHz, CDCl 3 ): δ 0.41 (s, 12H), 7.59-7.64 (m, 6H), 7.84-7.85 (m, 4H), 8.31 (s, 2H).

[0077] Carbon NMR (125 MHz, CDCl 3 ): δ 1.0, 125.6, 128.7, 129.1, 129.4, 130.3, 136.6, 152.3, 159.4.

[0078] Maximum absorption wavelength: 298 nm (6.3×10 2 / M -1 cm) (CH 2 Cl 2 ).

[0079] Maximum emission wavelength: 345 nm (CH 2 Cl 2 ).

[0080] Quantum yield: 13.1% (CH 2 Cl 2 ).

[0081]

[0082] 6c: Molecular formula: C 26 h 30 N 2 o 2 Si 3

[0083] Chinese name: 6,7-Dioxytrisilyl-1,4-diphenylphthalazine

[0084] English name: 6,7-Dioxatrisilole-1,4-diphenyl phthalazine

[0085] Molecular weight: 486.16

[0086] Appearance: yellow

[0087] H NMR (500 MHz, CDCl 3 ): δ 0.14 (s, 6H), 0.41 (s,...

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Abstract

The invention relates to a phthalazine or benzo phthalazine derivative and a preparation method thereof. The structure of the compound is shown in the specification, wherein R is-OCH3C6H4,-CH3C6H4,-C6H5,-ClC6H4, p-CF3C6H4 or o-C5H4N. The phthalazine or benzo phthalazine derivative is synthesized by the reaction of cycloaddition reaction and inverse cycloaddition reaction for loss of a molecule of nitrogen, the reaction is in accordance with the atom economic reaction requirements, provides a new thinking way for construction of phthalazine or benzo phthalazine skeletons, and enriches synthetic methods of organic heterocyclic compounds, the synthetic method of the phthalazine or benzo phthalazine derivative is not reported in the literature. From the analysis of performance test, the phthalazine or benzo phthalazine derivative has certain absorption and emission spectra, and the quantum yield of the benzo phthalazine derivative is higher.

Description

technical field [0001] The invention relates to a phthalazine or benzophthalazine derivative and a preparation method thereof. Background technique [0002] Phthalazine derivatives have certain biological activities and pharmaceutical uses, especially for proliferative diseases, such as the treatment of tumor diseases, inflammatory rheumatic and rheumatoid diseases and pain, diseases caused by neovascularization disorders such as ocular macular degeneration and Retinopathy, etc. [2] , 4-pyridylmethylphthalazine derivatives have been used in the preparation of drugs for the treatment of myelodysplastic syndrome. Phthalazine derivatives are also a new toner or accelerator, which are widely used in photosensitive thermal developing materials and PTG materials. Polymer materials containing phthalazine skeletons are a class of high-performance thermoplastic engineering materials with good thermal stability, chemical resistance and outstanding mechanical properties. They are in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10C07D237/26C07D401/14C09K11/06
Inventor 陈雅丽张亚娟徐迪陈炫名陈京大卢华丽
Owner SHANGHAI UNIV
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