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Double Hydroamination of Alkyne via PTC and Microwave‐activated Diastereoselective Synthesis of 2,3‐dihydroimidazo[1,2‐a]pyridine in an Aqueous Media
Author(s) -
Waseem Malik A.,
Lone Ali Mohd,
Ibad Farah,
Ibad Afshan,
Yadav Vijay B.,
Ansari Khursheed,
Shairjogrey Bashir Ahamad,
Watal Geeta,
Siddiqui I. R.
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2875
Subject(s) - chemistry , hydroamination , alkyne , catalysis , pyridine , imidazopyridine , acetylene , electrophile , combinatorial chemistry , organic chemistry
A novel facile and diastereoselective synthesis of imidazopyridine with high atom economy in water as a green solvent under synergic effect of microwave activation and phase transfer catalysis from readily available 2‐aminopyridine and electrophilic alkyne, dimethyl acetylene dicarboxylate has been developed. The strategy of the protocol involves heterocyclisation via double hydroamination of dimethyl acetylene dicarboxylate in biphasic system catalyzed by benzyltriethylammonium bromide activated by microwave irradiation. The transformation proceeded smoothly and quantitatively at an ambient temperature. The reaction sequence of the protocol was also proved by electrochemical synthesis of imidazopyridine using same starting materials under similar reaction conditions.