3-甲基-5-硝基呋喃衍生物的合成

SYNTHESIS AND BIOLOGICAL ACTIVITIES OF SOME NEW 3-METHYL-5-NITROFURA N DERIVATIVES

摘要: 本文报道在硝基呋喃类药物的呋喃环3位上进行结构修饰。根据3位甲基有利于硝基与酶活性部位的巯基进行亲核取代,有可能提高其抗菌杀虫活性的设想,合成了3-甲基呋喃嘧酮和3-甲基呋喃丙胺等新化合物19个。与母体化合物进行抗菌杀虫活性的比较,以探索环上甲基所起的作用。这类化合物的合成是以丙酮为原料,经Claisen缩合、Darzen反应、McFadyen反应成为3-甲基呋喃甲醛,再经Knoevenagel反应、硝化、缩合成为化合物Ⅰ。3-甲基呋喃醛经肟化、硝化、缩合成为化合物Ⅱ。有关生物活性比较和理论探讨将另文发表。

Abstract: Nineteen new compounds of 3-methyl-5-nitrofuran derivatives have been synthesized and their biological activities studied.3-Methyl-nitrofurans were synthesized from 3-methyl-2-furaldehyde obtained from methyl 3-methyl-2-furoate by McFadyen process, and the aldehyde condensed with malonic acid to form β-(3-methyl-2-furan) acrylic acid by Knoevenagel reaction. Nitration of the latter compound provided the key intermediate of β-(3-methyl-5-nitro-2-furan) acrylic acid, which was converted to compounds Ⅰ. The starting material for preparing compounds Ⅱ was 3-methyl-5-nitro-2-furaldehyde oxime obtained by nitration of 3-methyl-2-furaldehyde oxime.The biological activities of these compounds will be reported elsewhere.