Titanium Tetrachloride‐Mediated Approach to Access 2‐Chloro‐2‐Substituted Isoindolin‐1‐ones through the Addition of Alkynes to Acyliminium ions

2021 ◽  
Vol 2021 (18) ◽  
pp. 2625-2633
Author(s):  
Wen‐Ke Xu ◽  
Jia‐Ming Guo ◽  
Zhao‐Dan Chen ◽  
Chang‐Mei Si ◽  
Bang‐Guo Wei
Keyword(s):  
Titanium Tetrachloride ◽  
Acyliminium Ions

Synthesis of 5-Substituted 2-Pyrrolidinones by Coupling of Organozinc Reagents with Cyclic N-Acyliminium Ions

Synthesis ◽  
2019 ◽  
Vol 51 (24) ◽  
pp. 4650-4656
Author(s):  
Ivann Zaragoza-Galicia ◽  
Zaira A. Santos-Sánchez ◽  
Yazmín I. Hidalgo-Mercado ◽  
Horacio F. Olivo ◽  
Moisés Romero-Ortega
Keyword(s):  
Diethyl Ether ◽  
Boron Trifluoride ◽  
Titanium Tetrachloride ◽  
Reaction Medium ◽  
Coupling Reaction ◽  
Acyliminium Ions ◽  
Organozinc Reagents ◽  
Ether Complex ◽  
Organozinc Reagent

A coupling reaction between cyclic N-acyliminium ions with organozinc reagents is described. The cyclic N-acyliminium ions, generated in situ from N-substituted-5-hydroxy-2-pyrrolidinones by treatment with boron trifluoride–diethyl ether complex or titanium tetrachloride, are trapped by the organozinc reagent, which is formed from an alkyl bromide in the presence of zinc in the same reaction medium. The N-substituted-5-allyl-2-pyrrolidinones generated using this method serve as versatile intermediates for the synthesis of azabicyclic systems with indolizidine and pyrroloazepinolizidine cores.

Ammonolysis of titanium tetrachloride in liquid ammonia

1976 ◽  
Vol 73 ◽  
pp. 849-851 ◽  
Author(s):  
Thomas Kottarathil ◽  
Gérard Lepoutre
Keyword(s):  
Liquid Ammonia ◽  
Titanium Tetrachloride
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