Synthesis of chromeno[4,3-b]quinolines and spirobenzofuran-3,3′-quinolines through silver-mediated Appel reaction/C–Br bond cleavage/double selective rearrangement sequence

Various chromeno[4,3-b]quinolines and spirobenzofuran-3,3′-quinolines were prepared in good to excellent yields through a reduction and silver-mediated Appel reaction/sequential C–Br bond cleavage/double selective rearrangement cascade strategy from easily available chromeno[4,3-b]indolecarbaldehyde...

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Published in:Organic chemistry frontiers an international journal of organic chemistry 2019-07, Vol.6 (14), p.2334-2338
Main Authors: Hong-Ping, Zhao, Xiao-Pan, Ma, Shu-Min Nie, Xiao, Yuhong, Dong-Liang, Mo
Format: Article
Language:English
Subjects:
Cleavage
Crossovers
Crystallography
Migration
NMR
Nuclear magnetic resonance
Organic chemistry
Organic compounds
Quinoline
Quinolines
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container_title Organic chemistry frontiers an international journal of organic chemistry
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creator Hong-Ping, Zhao
Xiao-Pan, Ma
Shu-Min Nie
Xiao, Yuhong
Dong-Liang, Mo
description Various chromeno[4,3-b]quinolines and spirobenzofuran-3,3′-quinolines were prepared in good to excellent yields through a reduction and silver-mediated Appel reaction/sequential C–Br bond cleavage/double selective rearrangement cascade strategy from easily available chromeno[4,3-b]indolecarbaldehydes. Cross-over experiments revealed that the group migration occurred intramolecularly and the electronic effect on styrenyl groups had a little effect on the migration step. Two novel quinoline scaffolds were easily prepared on a gram scale by simple operation.
doi_str_mv 10.1039/c9qo00417c
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subjects Cleavage
Crossovers
Crystallography
Migration
NMR
Nuclear magnetic resonance
Organic chemistry
Organic compounds
Quinoline
Quinolines
title Synthesis of chromeno[4,3-b]quinolines and spirobenzofuran-3,3′-quinolines through silver-mediated Appel reaction/C–Br bond cleavage/double selective rearrangement sequence
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