Pyrrolobenzoxazepine ring construction through metalation and electrophilic substitution of N-[2-(hydroxymethyl)phenyl]pyrrole
N-[2-(hydroxymethyl)phenyl]pyrrole was found to be amenable to selective a-metalation. Trapping with a variety of electrophilic reagents afforded the expected products with moderate to high yields. Derivs. formed by treatment of the organometallic intermediate with aldehydes, ketones or carbon dioxide could be cyclized to give pyrrolobenzoxazepines. e.g., I (R = Ph, R1 = H, Me, Ph; R = CO2Me, R1 = Me; R = R1 = Me). [on SciFinder (R)]
Keywords: Lithiation (electrophilic substitution and ; of [(hydroxymethyl)phenyl]pyrrole); Substitution reaction (metalation and ; of [(hydroxymethyl)phenyl]pyrrole) ; pyrrolobenzoxazepine; benzoxazepine pyrrolo; metalation electrophilic substitution hydroxymethylphenylpyrrole; pyrrole hydroxymethylphenyl metalation electrophilic substitution
Heterocyclic Compounds (More Than One Hetero Atom)
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
written in English.
67-64-1 (Acetone); 98-86-2 (Acetophenone); 100-52-7 (Benzaldehyde); 119-61-9 (Benzophenone); 600-22-6 (Methyl pyruvate); 6784-61-8 Role: RCT (Reactant), RACT (Reactant or reagent) (electrophilic substitution of, with lithiated [(hydroxymethyl)phenyl]pyrrole); 61034-86-4 Role: RCT (Reactant), RACT (Reactant or reagent) (lithiation and electrophilic substitution of); 154601-85-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and intramol. cyclocondensation of); 154601-84-0P; 154601-86-2P; 154601-87-3P; 154601-88-4P; 154601-89-5P; 154601-90-8P; 154601-91-9P; 154601-92-0P; 154601-93-1P; 154601-94-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
Record created on 2006-03-03, modified on 2016-08-08