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

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 (R). 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.

Automated summary

An efficient, transition-metal-free, and practical one-pot sequential method for the synthesis of organochalcogenyl isoquinolinium imides was reported. The method showed good yields and short reaction times and could be applied to the synthesis of various organoselanyl and organosulfur imides.