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MOLECULAR DESIGN OF FUNCTIONALIZED HEHEROCYCLIC COMPOUNDS

功能化杂环化合物的分子设计

基本信息

批准号：
03650705
负责人：
NOGUCHI Michihiko
金额：
$ 1.28万
依托单位：
YAMAGUCHI UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1991
资助国家：
日本
起止时间：
1991 至 1992
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-03650705/
关键词：
FUNCTIONALIZED HETEROCYCYCLES MOLECULAR DESIGN DIENE SYSTEMS ON THE PERIPHERY OF HETEROCYCLES *4+2*CYCLOADDITION 1,3-DIPOLAR CYCLOADDITION INTRAMOLECULAR ENE REACTION CROSSED CONJUGATED ALDEHYDE SYSTEMS FUNCTIONALIZED CARBODIIMIDES 二環性グアニジ

项目摘要

This project has been directed toward the development of synthetic accesses to functionalized heterocyclic compounds. The results obtained are demonstrated as belows; 1.A 5,6-dihydro-5,6-bis(methylene)-2,4(1H,3H)-pyrimidinedione intermediate was generated by the treatment of 5-formyl-1,3,6-trimethyl-2,4 (1H,3H)-pyrimidinedione with magnesium salt and DBU. The enolate underwent[4 + 2]cycloaddition reaction with olefins in highly regio-and stereoselective manners. By similar methods,enolates in 4(1H)-pyridone and DELTA^3-phrazolin-5-one systems were obtained and the cycloaddition reactions using these enolates leading to quinolines and indazoles were investigated. 2.The reaction of 6-alkenylamino-5-formyl-1,3,6-trimethyl-2,4(1H,3H)-pyrimidinedione with alpha-amino acid derivatives afforded intramolecular azomethine ylide adducts and ene reaction products. The reaction paths depended on the nature of the amino acids;the reaction with N-substituted amino acid derivatives gave azomethine ylide intermediates. On the other hand,the reaction with N-unsabstituted ones gave the imines as intermediates,which underwent imine-ene reaction to form fused azepines. Similar bident reaction profiles were elucidated in the reactions of 2(1H)-pyridone,chromenone,and pyridopyrimidine systems. 3.Functionalized carbodiimides were used as a synthetic building block for heterocyclic systems such as pyridine,pyrimidine,and imidazole.

该项目旨在开发官能化杂环化合物的合成途径。主要研究结果如下：1.5-甲酰基-1，3，6-三甲基-2，4(1H，~3H)-嘧啶二酮与镁盐和二溴联苯并呋喃反应生成5，6-dihydro-5，6-bis(methylene)-2，4(1H，3H)-pyrimidinedione中间体。烯酸酯与烯烃发生[4+2]环加成反应，具有很高的区域选择性和立体选择性。用类似的方法得到了4(1H)-吡啶酮和Delta、3-吡唑啉-5-酮体系中的烯醇类化合物，并考察了它们与喹啉和吲唑类化合物的环加成反应。2.6-alkenylamino-5-formyl-1，3，6-trimethyl-2，4(1H，3H)-pyrimidinedione与α-氨基酸衍生物反应生成了分子内的甲亚胺叶立德加合物和烯反应产物。反应路径取决于氨基酸的性质；与N-取代氨基酸衍生物反应生成亚甲基叶立德中间体。另一方面，与N-未取代氮杂环己烷反应得到亚胺类中间体，亚胺-烯反应生成稠合氮杂环丙烷。在2(1H)-吡啶酮、色素酮和吡啶并嘧啶体系的反应中也发现了相似的Bident反应谱。3.将功能化碳二亚胺用作合成吡啶、嘧啶和咪唑等杂环体系的构筑基块。