苯並呋喃及異吲哚啉酮並異喹啉衍生物之合成

Abstract

本論文分為兩部分，第一部分主要探討硝基化合物的化學，主題為萘並呋喃 衍生物的合成，利用簡單的一鍋化方式在鹼性條件下進行反應，首先β-硝基烯衍生物及2-萘酚於室溫下先進行1,4-麥可加成後再進行分子內合環反應，於溫和的條件下得到產率相當不錯的多種萘並呋喃衍生物 。

第二部分主要探討以2-碘苯甲醯胺衍生物與末端炔為起始物經由兩步驟合 成異吲哚啉酮稠合異喹啉的衍生物，第一步利用銅試劑催化進行薗頭耦合反應及分子內合環得到多種異吲哚啉酮衍生物且有相當不錯的產率，第二部則是利用醋酸鈀催化分子內赫克反應合成出異吲哚啉酮稠合異喹啉的衍生物，兩步均利用低催化劑量的催化劑及溫合的條件即可得乾淨且產率不錯的產物 。The content of the thesis is divided into two parts. The first part focuses on the chemistry of the nitro alkenes and its application in the synthesis of naphthofuran derivatives. The methodology is based on one-pot base mediated tandem reaction of β-nitrostyrene derivatives and 2-naphthol, 1,4-Michael addition and intramolecular cyclization. A wide variety of naphthofuran derivatives were synthesized in relatively good yields under mild condition.

The second part describes about the synthesis of fused isoindolinone and isoquinoline derivatives in two step processes starting from 2-iodobenzamide derivatives and terminal alkynes. In the first step, copper(II) catalyst was used for the Sonogashira coupling and intramolecular cyclization in the reaction of 2-iodobenzamide derivatives and terminal alkynes to obtain isoindolinone derivatives in good excellent yields. The second step is an intramolecular Heck reaction which was catalyzed by palladium diacetate. In both steps the catalyst loading was low and the desired products were obtained in moderate yields. The conditions used here are mild and reactions are clean in most the cases.