ABSTRACT
The one-pot four-component reaction of 3-(1H-indol-3-yl)-3-oxopropanenitriles, aromatic aldehydes, cycloalkanones and ammonium acetate occurred via a six-step tandem Knoevenagel condensation-nucleophilic addition to carbonyl-Michael addition-N-cyclization-elimination-air oxidation sequence to afford structurally intriguing indole-cycloalkyl[b]pyridine-3-carbonitrile hybrid heterocycles in excellent yields.
ABSTRACT
The combinatorial syntheses of a library of novel dihydrothiophenone-engrafted dispiro oxindole/indenoquinoxaline-pyrrolidine/pyrrolothiazole/indolizine hybrid heterocycles have been realized through a chemo-, regio-, and stereoselective multicomponent 1,3-dipolar cycloaddition strategy.
Subject(s)
Heterocyclic Compounds, Fused-Ring/chemical synthesis , Small Molecule Libraries/chemical synthesis , Spiro Compounds/chemical synthesis , Thiophenes/chemical synthesis , Combinatorial Chemistry Techniques , Cycloaddition Reaction , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Structure , Stereoisomerism , Structure-Activity RelationshipABSTRACT
The stereoselective syntheses of a library of novel spiro-tethered pyrazolo[3,4-b]quinoline-pyrrolidine/pyrrolothiazole/indolizine-oxindole/acenaphthene hybrid heterocycles have been achieved through the 1,3-dipolar cycloaddition of azomethine ylides generated in situ from α-amino acids and 1,2-diketones to dipolarophiles derived from pyrazolo[3,4-b]quinoline derivatives.
