Five-membered rings 3-position single-substituted benzosultam derivatives and preparation method thereof

Abstract

The invention relates to a five-ring three-substituted benzo sultam derivative and the preparation method, belonging to the field of chemical technology. The derivative has such a structure as shown in the formula (I): R1 = hydrogen, alkyl, methoxy, halogen and so on; R2 and R3 = alkyl, aryl, miscellaneous aryl, miscellaneous alkyl, and so on. The preparation method uses the N-tert-butyl - benzene sulfonamide derivatives as the raw material; with the influence of the positive butyl lithium, react to form the negative ions of carbon; then react with the benzaldehyde containing the methoxy and other substituting functional groups to form the middle alcohol. Optimize the cyclization conditions, such as the adjustment of the consumption of the TMSC1/NaI/MeCN reagent, the addition of the reaction aid, the control of the reaction temperature and reaction time and so on, to synthesize a series of five-ring benzo sultam derivative.

Description

technical field [0001] The invention relates to a derivative and a preparation method thereof, in particular to a 3-position monosubstituted benzosultam derivative of a five-membered ring and a preparation method thereof. Background technique [0002] The 3-monosubstituted benzosultam derivatives of the five-membered ring are a new class of compounds with antitumor and antiviral effects. The five-membered ring benzosultam derivatives usually use cheap saccharin as a raw material, and react with organometallic reagents to form sullimides. The chiral 3-position monosubstituted five-membered ring benzosultam can be obtained by chiral reduction of the sultone; the sultone can also be further reacted with an organometallic reagent to obtain a 3-position disubstituted derivative. Its synthetic route is as follows: [0003] [0004] [0005] However, this method has two disadvantages: the one is that saccharin has poor reactivity and low yield with most organometallic reage...

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Problems solved by technology

[0005] However, this method has two disadvantages: the one is that saccharin has poor reactivity and low yield with most organometallic reagents, especially the larger Grignard reagents; the other is the types of available metal lithium or Grignard reagents Limited, organometallic reagents with functional groups (such as amino groups, phenolic hydroxyl groups, etc.) cannot or are difficult to prepare

[0009] Although this synthesis method can obtain the target compound, since the 3-position substituent always has a methylene group connected to the mother ring, and most of the reagents used are relatively expensive, it cannot meet the requirements of synthesizing the 3-position monosubstituted benzos of five-membered rings with diverse structures. Requirements for sultam derivatives

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