Premium
Exploiting the Divergent Reactivity of Isocyanoacetates: One‐Pot Three‐Component Synthesis of Functionalized Angular Furoquinolines
Author(s) -
Bouma Marinus J.,
Masson Géraldine,
Zhu Jieping
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101567
Subject(s) - chemistry , reactivity (psychology) , reagent , quinoline , toluene , methanol , domino , component (thermodynamics) , organic chemistry , sequence (biology) , combinatorial chemistry , ring (chemistry) , catalysis , medicine , biochemistry , physics , alternative medicine , pathology , thermodynamics
A one‐pot, three‐component synthesis of polysubstituted furo[2,3‐ c ]quinoline 1 was developed based on the new reactivity profile of α‐(4‐nitrophenyl)‐α‐isocyanoacetates. Simply mixing aldehydes 2 , ortho ‐alkynylanilines 3 , and α‐(4‐nitrophenyl)‐α‐isocyanoacetates 4 in methanol at room temperature, followed by addition of toluene and heating to reflux, provided the polysubstituted furo[2,3‐ c ]quinolines in moderate to excellent yields. Mechanistically, the three‐component reaction of 2 , 3 , and 4 leading to 5‐alkoxyoxazoles was followed by a domino sequence involving Diels–Alder/retro‐Diels–Alder/oxidation reactions. In this one‐pot process, five chemical bonds were created with concurrent formation of two heterocyclic rings. The reaction was performed under thermal conditions and no external reagent was needed to promote this mechanistically intriguing reaction.