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Transition‐Metal‐Free Synthesis of Nitrogen Containing Heterocycles With Fully Substituted N ‐fused Pyrrole Rings
Author(s) -
Bakshi Debanjan,
Singh Anand
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500324
Subject(s) - chemistry , pyrrole , indolizine , quinoline , isoquinoline , cycloaddition , alkylation , combinatorial chemistry , ring (chemistry) , 1,3 dipolar cycloaddition , reactivity (psychology) , alkyl , stereochemistry , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
The efficient synthesis of C‐2 alkylated indolizine, pyrrolo[1,2‐ a ]isoquinoline, and pyrrolo[1,2‐ a ]quinoline derivatives utilizing a single reactivity platform is described. Employing a [3+2] dipolar cycloaddition reaction between heterocyclic N ‐ylides and allenoates, the incorporation of C‐2 alkyl substituents was achieved resulting in various N ‐fused heterocycles with a fully substituted pyrrole ring. This metal‐free route employing allenoates as a dipolarophile solves the longstanding limitations of functional diversity at the C‐2 position and the efficient creation of the pyrrolo[1,2‐ a ]quinoline motif.