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1-alkyl-1,6-dihydro-1,2,4,5-tetrazine compound and synthesis method thereof

A synthesis method and compound technology are applied in the field of chemistry to achieve the effects of high yield, mild reaction conditions, and easy separation and purification

Inactive Publication Date: 2011-04-06
TAIZHOU VOCATIONAL & TECHN COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, there are few studies on 1-alkyl-1,6-dihydro-1,2,4,5-tetrazine compounds, especially for 3,6 asymmetric 1-alkyl- The synthesis method of 1,6-dihydro-1,2,4,5-tetrazine has not been reported in the literature

Method used

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  • 1-alkyl-1,6-dihydro-1,2,4,5-tetrazine compound and synthesis method thereof
  • 1-alkyl-1,6-dihydro-1,2,4,5-tetrazine compound and synthesis method thereof
  • 1-alkyl-1,6-dihydro-1,2,4,5-tetrazine compound and synthesis method thereof

Examples

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Embodiment 1

[0041] Example 1: Synthesis of 1-benzyl-3-phenyl-6-methyl-1,6-dihydro-1,2,4,5-tetrazine.

[0042] Mix 1.0mmol 3-phenyl-6-methyl-1,6-dihydro-1,2,4,5-tetrazine, 1.0mmol lithium hydroxide monohydrate and 10ml methanol, add 1.0mmol dropwise at 0°C 10ml of methanol solution of benzyl bromide, after the dropwise addition, keep warm for half an hour, then react at room temperature for 5 hours, recover methanol under reduced pressure to obtain a yellow solid, and purify by column chromatography to obtain a yellow crystalline solid 1-benzyl-3-benzene The yield of 6-methyl-1,6-dihydro-1,2,4,5-tetrazine was 82%.

[0043] Elemental analysis is as follows: mp: 101-103°C;

[0044] IR v max(KBr) / cm -1 : 3064, 2986, 1636, 1455, 1406, 1356, 1161, 1071, 764, 736, 695;

[0045] 1 H NMR (400MHz, CDCl 3 )δppm: 7.98 (d, 2H, J = 7.6Hz), 7.44 (t, 2H, J = 7.8Hz), 7.30-7.37 (m, 4H, ArH), 7.17 (d, 2H, J = 6.8Hz), 4.84(s, 2H), 2.95(q, 1H, J=6.1Hz), 1.84(d, 3H, J=6.4Hz);

[0046] MS (m / z, %): 236 (...

Embodiment 2

[0048] Example 2: Synthesis of 1-benzyl-3-phenyl-6-methyl-1,6-dihydro-1,2,4,5-tetrazine

[0049] Benzyl chloride was used instead of benzyl bromide, and the reaction time was extended to 10 hours to obtain a yellow solid with a yield of 70%; other methods were the same as in Example 1, and will not be repeated.

Embodiment 3

[0050] Example 3: Synthesis of 1-benzyl-3-phenyl-6-methyl-1,6-dihydro-1,2,4,5-tetrazine

[0051] Sodium hydroxide was used instead of lithium hydroxide monohydrate to obtain a yellow solid with a yield of 76%. The other methods were the same as in Example 1, and will not be repeated.

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Abstract

The invention relates to a new 1-alkyl-1,6-dihydro-1,2,4,5-tetrazine compound and a synthesis method thereof. The tetrazine compound is shown as general formula (I), wherein, R1 represents one of H, halogen and alkyl, and R2 represents one of C1-20 alkane group, benzyl and a benzyl derivative. The compound adopts an asymmetric boat-type structure and has homoaromaticity and potential physiological activity; and the synthesis method has the advantages of moderate reaction conditions, short reaction time, higher yield, easy mass production, potential industrialized value, and effectively reduced degradation degree of 1,6-dihydro-1,2,4,5-tetrazine in an alkaline solution.

Description

technical field [0001] The invention relates to a tetrazine compound and a synthesis method thereof, in particular to a 1-alkyl-1,6-dihydro-1,2,4,5-tetrazine compound and a synthesis method thereof, belonging to the technical field of chemistry. Background technique [0002] Tetrazine, also known as tetraazine, is a six-membered heterocyclic compound containing 4 nitrogen atoms. There are 1,2,3,4-, 1,2,4,5- and 1,2,3,5-tetrazine three isomers. The more important one is 1,2,4,5-tetrazine, which is soluble in water, alcohol and ether. It is widely used in the fields of pesticides, dyes, explosives and liquid crystals (see Brooker, P.J.; Parsons, J.H.; Reid, J.; West, P.J. Pesfic.Sci.1987, 18, 179; Saftien, K.; Anton, E .German Patent: DE 923028,1955; Hiskey, M.; Goldman, N.; Stine, J.J.Energ.Mater.1998, 16, 119. and Sun, X.-C.; Ren, G.-D.Chin. J. Org. Chem. 1988, 8, 365.). In addition, 1,2,4,5-tetrazine compounds have various physiological activities, such as antiviral, an...

Claims

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Application Information

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IPC IPC(8): C07D257/08
Inventor 徐峰杨珍珍柯中炉闫启东杨伟群陈建军陈红云
Owner TAIZHOU VOCATIONAL & TECHN COLLEGE
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