Synthesis of pyrrolo[2,1-c[1,4]benzodiazepines via reductive cyclization of omega-azido carbonyl compounds by TMSI: an efficient preparation of antibiotic DC-81 and its dimers.
Azido carbonyl compounds on reaction with trimethylsilyl iodide (in situ prepared from TMSCl/NaI) led to the formation of diazepine imines in good yields under mild conditions. This methodology has been applied to the parent unsubstituted pyrrolobenzodiazepine, the natural product DC-81 and its dimers.
Kamal
A
A
Division of Organic Chemistry--I, Indian Institute of Chemical Technology, Hyderabad. ahmedkamal@iict.ap.nic.in
Laxman
E
E
Laxman
N
N
Rao
N V
NV
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000737:chemistry; D019281:Dimerization; D007202:Indicators and Reagents; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012974:Sodium Iodide; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry; D014297:Trimethylsilyl Compounds
D000900:Anti-Bacterial Agents; D001381:Azepines; D007202:Indicators and Reagents; D011758:Pyrroles; D014230:Triazoles; D014297:Trimethylsilyl Compounds; C419804:trimethylsilyl iodide; D001569:Benzodiazepines; D012974:Sodium Iodide