Synthesis of 2,3-Dihydrofuro[3,2-c]pyridine-3,4-dicarboxylic Acid, a Conformationally Constrained Analogue of the Subtype Selective NMDA Receptor Agonist Homoquinolinic Acid
作者:Robert H. Dodd、Marcus Vinicius Nora de Souza、Zhaohua Yan
DOI:10.3987/com-04-s(p)22
日期:——
the sodium salts of allyl alcohol and propargyl alcohol, respectively, were subjected to tri-n-butyltin hydride/AIBN free radical cyclization conditions. While the propargylic compound (15) did not cyclize, the allylic compounds (8, 28) cyclized in the presence of diphenyl diselenide, TEMPO or oxygen as radical trapping agents to give the corresponding 2,3-dihydrofuro[3,2-c]pyridine-4-carboxylic acid
通过 4-chloro-2-iodopicolinanilides (11,14) 分别与烯丙醇和炔丙醇的钠盐反应获得的 4-Allyloxy- 和 4-prop-2-ynyloxy-3-iodopicolinic acid 衍生物,到氢化三正丁基锡/AIBN自由基环化条件。虽然炔丙基化合物 (15) 不环化,但烯丙基化合物 (8, 28) 在二苯基二硒化物、TEMPO 或氧作为自由基捕获剂的存在下环化,得到相应的 2,3-二氢呋喃[3,2-c]吡啶-4-羧酸衍生物在 C-3 处分别被苯基硒基甲基 (20)、2,2,6,6-四甲基哌啶-1-基氧基甲基 (22) 或羟甲基 (29) 取代。