One‐pot Sequential Strategy to Prepare Organoselanyl and Organotellanyl Isoquinolinium Imides

Abstract

Herein, we report an efficient, transition‐metal‐free and practical one‐pot sequential method for the synthesis of organochalcogenyl isoquinolinium imides. In this one‐pot two‐steps approach, N′‐(2‐alkynylbenzylidene) hydrazides were firstly prepared under ultrasound irradiation, followed by the addition of diorganyl dichalcogenides and Oxone®. A total of 25 organoselanyl isoquinolinium imides, being 22 unprecedented in the literature, were obtained in good to excellent yields (79–95 %) in short reaction times (30–70 min) using a range of 2‐alkynyl aldehydes and diaryl, dialkyl, and diheteroaryl diselenides as substrates. The methodology was extended to tellurium, affording for the first time, tellurium isoquinolinium imides, in good yields (70–80 %) after 120 min of reaction.

Recent Progress in Synthetic and Biological Application of Diorganyl Diselenides

“…Organoselenyl isoquinolinium imides and isoquinoline-N-oxides can also be prepared from diorganyl diselenides using Oxone instead of iron(III) chlorides. [110,111] Oxygen from carboxylic acid derivatives was also suitable nucleophiles in cyclization reactions promoted by diorganyl diselenides. We developed two methodologies using alkynylanilides and alkynylbenzamides as substrates in the cyclization reactions promoted by diorganyl diselenides.…”

“…Next, the 6‐ endo‐dig cyclization occurs via a nucleophilic attack on the activated carbon‐carbon triple bond to afford the products. Organoselenyl isoquinolinium imides and isoquinoline‐ N ‐oxides can also be prepared from diorganyl diselenides using Oxone instead of iron(III) chlorides [110,111] …”