A New Flow Methodology for the Expedient Synthesis of Drug‐Like 3‐Aminoindolizines | Zendy

Lange Paul P. | Zendy; Bogdan Andrew R. | Zendy; James Keith | Zendy

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A New Flow Methodology for the Expedient Synthesis of Drug‐Like 3‐Aminoindolizines

Author(s) -

Lange Paul P.,

Bogdan Andrew R.,

James Keith

Publication year - 2012

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.201200316

Subject(s) - chemistry , sonogashira coupling , combinatorial chemistry , tandem , cycloisomerization , flow chemistry , yield (engineering) , continuous flow , catalysis , nanotechnology , organic chemistry , biochemical engineering , palladium , materials science , engineering , metallurgy , composite material

A flow‐based synthesis of diversely functionalized indolizines and their aza‐analogues is described. These drug‐like heterocycles were generated via a tandem Sonogashira/cycloisomerization sequence, starting from widely available 2‐bromopyridines and alkynes, employing a simple catalyst system together with 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) as base. The use of flow technology allows a straightforward and rapid access to a variety of novel compounds, and enables linear scale‐up from milligram‐ to gram‐scales without a decrease in yield.

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