Access to pyrrolo- and pyrido[1,2-a]indole derivatives by intramolecular nitrone cycloadditions. Effect of steric factors on the regioselective product formation.
On starting from N-allyl-substituted 2-indolecarbaldehydes and exploiting the intramolecular nitrone cycloaddition methodology, we synthesized a number of the title fused-ring indole derivatives in racemic as well as enantiopure form.
Beccalli
E M
EM
Istituto di Chimica Organica della Facoltà di Farmacia dell'Università di Milano, via Venezian 21, 20133 Milano, Italy.
Broggini
G
G
La Rosa
C
C
Passarella
D
D
Pilati
T
T
Terraneo
A
A
Zecchi
G
G
D018360:Crystallography, X-Ray; D003500:Cyclization; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009589:Nitrogen Oxides / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D007202:Indicators and Reagents; D007211:Indoles; D009589:Nitrogen Oxides; C015388:nitrones