Novel biphenyl tetrazole derivative and preparation method thereof

Abstract

The invention relates to a novel biphenyl tetrazole derivative. A chemical general molecular formula of the novel biphenyl tetrazole derivative is shown as the accompanying drawing. The invention also relates to a preparation method of the novel biphenyl tetrazole derivative. A synthesis path is shown as the accompanying drawing, wherein n is selected from 0, 1, 2, 3, 4 and 5; Y is selected from -Br, -Cl, -NO2 and a substance shown as the accompanying drawing; R1, R2 and R3 are selected from -H, mono-substituted or poly-substituted -F, -(CH2)mCH3, -(CH2)mCF3, -O(CH2)mCH3, -O(CH2)mCF3 and -NO2 groups; m is selected from 0, 1, 2, 3, 4 and 5. The method comprises the operation steps that a compound II and 1,4-diazido dicyclic [2.2.2] octane are dissolved into a mixed reaction solution of a first organic solvent and carbon disulfide; filtering is performed to obtain yellow solids; after washing drying, the materials are dissolved into a second organic solvent; triphosgene or diphosgene is added; or phosgene reaction is performed; filtering is performed; filter liquid is collected; concentration is performed to obtain a crude product; the crude product is dissolved into a third organic solvent; ammonia water is added; concentration is performed to obtain yellow solid crude products; the solid crude products are dissolved into a four organic solvent; then, NaN3, I2 and organic amine NHpR<3-p> are sequentially added into the organic solvent; basic water solution is added for quenching reaction; a fifth organic solvent is used for extracting the organic layer; concentration and purification are performed; a compound III is obtained.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to biphenyltetrazolium derivatives and a preparation method thereof. Background technique [0002] Amino tetrazole derivatives have a wide range of applications. Taking the field of medicine as an example, many tetrazole derivatives have biological activity and can be developed as potential drug candidate molecules. [0003] However, the methods for the preparation of aminotetrazoles reported in the existing literature, A.N.Vorobiov et al. Acid reagents are highly toxic reagents and are relatively dangerous; Hg, Pb Salt is a heavy metal salt that has serious damage to the environment; [Behzad Khalili Faramarz Sadeghzadeh Darabi Bagher Eftekhari-Sis Mehdi Rimaz, Monatsh Chem (2013) 144:1569–1572.] The Zr used in the method is Expensive metal reagents are expensive to use and are not suitable for large-scale industrial production. [0004] K.Patel research group [Ramesh Yella, Nilu...

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Problems solved by technology

[0003] However, the methods for the preparation of aminotetrazoles reported in the existing literature, A.N.Vorobiov et al. Acid reagents are highly toxic reagents and are relatively dangerous; Hg, Pb Salt is a heavy metal salt that has serious damage to the environment; [Behzad Khalili Faramarz Sadeghzadeh Darabi Bagher Eftekhari-Sis Mehdi Rimaz, Monatsh Chem (2013) 144:1569–1572.] The Zr used in the method is Expensive metal reagents, high cost of use, not suitable for large-scale industrial production

[0004] K.Patel research group [Ramesh Yella, Nilufa Khatun, Saroj Kumar Rout and BhismaK.Patel, Org.Biomol.Chem., 2011,9,3235.] studied using thioisocyanate as raw material, using ammonia, sodium azide, Iodine and triethylamine prepared tetrazole in one pot, but the yield was too low, only 10%!

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