Halogenoalkyl isocyanates as bifunctional reagents in an Aza-Wittig/heterocyclization reaction on the solid phase: efficient entry into new tetracyclic benzimidazole systems.
An efficient one-pot procedure for the solid-phase synthesis of new tetracyclic 1,3,5-triazino[1,2-a]benzimidazolium derivatives starting from resin-bound benzimidazoles is described. The synthetic strategy involves an unprecedented one-pot Aza-Wittig/heterocyclization/substitution reaction sequence using halogenoalkyl isocyanates. The structure of the tetracyclic ring system was determined by two-dimensional NMR experiments and X-ray analysis.
Hoesl
Cornelia E
CE
Torrey Pines Institute for Molecular Studies, 3550 General Atomics Court, San Diego, CA 92121, USA.
Nefzi
Adel
A
Houghten
Richard A
RA
D000478:Alkylation; D001562:Benzimidazoles / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D003500:Cyclization; D006219:Halogens / Q000737:chemistry*; D017953:Isocyanates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry*; D012117:Resins, Synthetic; D013237:Stereoisomerism
D001562:Benzimidazoles; D006219:Halogens; D017953:Isocyanates; D011083:Polycyclic Compounds; D012117:Resins, Synthetic