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Synthesis of New Furo[3,4‐ b ]quinolin‐1(3 H )‐one Scaffolds Derived from γ ‐Lactone‐Fused Quinolin‐4(1 H )‐ones
Author(s) -
Labruère Raphaël,
Helissey Philippe,
DesbèneFinck Stéphanie,
GiorgiRenault Sylviane
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200313
Subject(s) - chemistry , lactone , aniline , quinoline , methylenedioxy , stereochemistry , context (archaeology) , amine gas treating , lactam , combinatorial chemistry , organic chemistry , paleontology , alkyl , halogen , biology
In the context of our aim of discovering new antitumor drugs among synthetic γ ‐lactone‐ and γ ‐lactam‐fused 1‐methylquinolin‐4(1 H )‐ones, we developed a rapid access to 5‐methyl‐1,3‐dioxolo[4,5‐ g ]furo[3,4‐ b ]quinoline‐8,9(5 H ,6 H )‐dione ( 9 ) exploiting the γ ‐lactone‐fused chloroquinoline 10 previously synthesized in our laboratory ( Scheme 1 ). We also elaborated efficient synthetic methods allowing for a rapid access to two nonclassical bioisosteres of 9 , i.e. , a deoxy and a carba analogue. The deoxy analogue 11 was prepared in two steps from the γ ‐lactone‐fused quinoline 13 which was also the synthetic precursor of 10 ( Scheme 1 ). The carba analogue 6,9‐dihydro‐5‐methyl‐9‐methylene‐1,3‐dioxolo[4,5‐ g ]furo[3,4‐ b ]quinolin‐8(5 H )‐one ( 12 ) was easily prepared by HCl elimination from the 9‐(chloromethyl)dioxolofuroquinoline 15 , which was obtained via a three‐component one‐pot reaction from N ‐methyl‐3,4‐(methylenedioxy)aniline (= N ‐methyl‐1,3‐benzodioxol‐5‐amine; 16 ), commercially available chloroacetaldehyde, and tetronic acid ( 17 ) ( Scheme 2 ).