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 add...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-11, Vol.2022 (43), p.n/a
Main Authors: Goulart, Helen A., Araujo, Daniela R., Barcellos, Angelita M., Jacob, Raquel G., Lenardão, Eder J., Perin, Gelson
Format: Article
Language:English
Subjects:
Aldehydes
Cyclization
Green Chemistry
Hydrazides
Imides
Isoquinoline
Selenides
Selenium
Substrates
Tellurium
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Summary: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. Here report a one‐pot two‐steps approach to prepare organoselanyl and organotellanyl isoquinolinium imides by the 6‐endo‐dig electrophilic cyclization of N′‐(2‐alkynylbenzylidene)hydrazides using diorganyl diselenides/ditellurides and Oxone® under ultrasound irradiation.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202201027