- Highly efficient one-pot amination of carboxylate-substituted nitrogen-containing heteroaryl chlorides via Staudinger reaction
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An efficient one-pot method for the synthesis of tert-butyl 6-aminonicotinate (5) is described. The key transformation involves displacement of the chloro group in tert-butyl 6-chloronicotinate (2) with azide followed by a Staudinger reaction. The scope of this methodology is further extended for the synthesis of a series of carboxylate-substituted heteroaryl amines. In particular, we synthesized tert-butyl carboxylate-substituted amino-pyridine, -pyridazine, and -pyrazine. In addition to one-pot conversion, short reaction time, simplicity of operation, ease of purification, and good yields are the key advantages of this methodology.
- Kandalkar, Sachin R.,Kaduskar, Rahul D.,Ramaiah, Parimi Atchuta,Barawkar, Dinesh A.,Bhuniya, Debnath,Deshpande, Anil M.
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supporting information
p. 414 - 418
(2013/02/23)
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- A MILD CONVENIENT SYNTHESIS OF HETEROCYCLIC TRIPHENYLPHOSPHINE IMINES
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A series of heterocyclic phosphine imines (1,3,5-triazines, pyrazines, pyridines, furazans and furoxans) have been readily prepared by direct action of N-trimethylsilyl-P,P,P-triphenylphosphine imine on chloro- or nitro derivatives. Key words: Triphenylphosphine imines; heterocycles; trimethylsilyltriphenylphosphine imine.
- Rakitin, Oleg A.,Obruchnikova, Natalia V.,Khmelnitski, Lenor I.
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p. 309 - 312
(2007/10/02)
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