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Iron(III)‐Promoted Synthesis of 3‐(Organoselanyl)‐1,2‐Dihydroquinolines from Diorganyl Diselenides and N ‐Arylpropargylamines by Sequential Carbon‐Carbon and Carbon‐Selenium Bond Formation
Author(s) -
Goulart Tales A. C.,
Kazmirski João A. G.,
Back Davi F.,
Zeni Gilson
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801097
Subject(s) - chemistry , nitromethane , surface modification , diselenide , reactivity (psychology) , nucleophile , tandem , carbon fibers , selenium , combinatorial chemistry , polymer chemistry , inorganic chemistry , organic chemistry , catalysis , medicine , materials science , alternative medicine , pathology , composite number , composite material
The iron‐promoted tandem cyclization‐functionalization reaction of N ‐arylpropargylamines with diorganyl diselenides was developed for the preparation of 3‐(organoselanyl)‐1,2‐dihydroquinolines. The best result was obtained when the reaction of N ‐arylpropargylamines was carried out by the combination of diorganyl diselenides with FeCl 3 ⋅ 6H 2 O in nitromethane at 70 °C. The control experiments strongly support the cooperative relation between the iron salts and diorganyl diselenides and their high reactivity not only to promote the cyclization but also to introduce a functionalization at the 3‐position of dihydroquinolines. The results indicate the existence of an iron/diorganyl diselenide complex, which forms both a cation and an anion of organoselenyl. In an attempt to prove the synthetic application of 3‐(organoselanyl)‐1,2‐dihydroquinolines prepared, we evaluated their use as substrates in the transition metal‐catalyzed cross‐coupling reactions with nucleophiles, such as boronic acids.