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Discovery of Pyrimidine Benzylamine Diphenyl Ether Leads and Mechanistic Study on a Novel LiAlH4-promoted Reductive Rearrangement of Benzamide Derivatives Via Neighboring-pyrimidine Participation

Author: ChenMeiFeng
Tutor: WuJun
School: Zhejiang University
Course: Organic Chemistry
Keywords: Herbicide Pyrimidine benzylamine Reduction Lithium aluminum hydride
CLC: O621.25
Type: Master's thesis
Year: 2006
Downloads: 173
Quote: 0
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Abstract


The first chapter summarizes the pyrimidine compounds are an important class of biologically active substances, heterocyclic pyrimidine-based studies have been conducted herbicides given adequate attention in recent years there have been many new herbicides. Benzylamine and its derivatives have a variety of biological activities, ortho-substituted benzyl amine pyrimidine compounds we have found a class of unique structure, with a high herbicidal activity of new lead compounds, design and synthesis of pyrimidines having a high weeding activity benzyl amine compound is our working goal. Chapter conducted a pyrimidine benzylamine Diphenyl Ethers Design, Synthesis and herbicidal activity. Pyrimidine and ether compounds with molecular basic structural unit, designed a new type of pyrimidine benzylamine ether molecule libraries, fifteen kinds of new pyrimidine synthesis benzyl amines pilot structure, its infrared and NMR verification spectrum of the target molecule library molecule biological activity screening studies, compounds gramineous weeds 25,70,71 and 73 exhibit excellent herbicidal activity against barnyard grass and crabgrass inhibition rate reaches 9, the activity and the substituent on the phenyl ring, in order to identify the structure and activity of the compound and the relationship between better herbicide. Chapter literature through improved method for 6 - benzyl amine substituted pyrimidine compounds and intermediates of the synthesis route design synthesis, synthesis of a key 6 - substituted intermediate 76, to find a better synthetic route to 6 - substituted pyrimidine benzylamine foundation. Through a large number of experiments and found that the iron powder as a reducing agent, FeCl 2 .4 H 2 O, and NH 4 Cl was mixed catalyst, methanol / water as solvent at a reaction system that can be successfully restored polyfunctional compound containing 2 - acetyl-6 - nitrobenzoate, improved reaction, the reaction rate is greatly improved, the degree of hydrolysis to obtain a better control, the viability of the route greatly increased. Chapter IV of lithium aluminum hydride reduction thio pyrimidine amides did not obtain the expected product accidentally separated into pyrimidine amine compounds and 2 - mercapto this strange reaction of benzyl alcohol from the receptor structure changes, LiAlD 4 tag test, intramolecular and intermolecular nucleophilic substitution reactions and crystal structure and other aspects to explore this strange reaction, proposed reaction mechanism, to explore new methods and organic synthesis pathway.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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