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)]


Published in:
Tetrahedron, 50, 7, 2071-6
Year:
1994
Keywords:
Note:
CAN 120:270340
28-22
Heterocyclic Compounds (More Than One Hetero Atom)
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4020
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)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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