Pyrrolobenzoxazepine ring construction through metalation and electrophilic substitution of N-[2-(hydroxymethyl)phenyl]pyrrole
1994
Abstract
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)]
Details
Title
Pyrrolobenzoxazepine ring construction through metalation and electrophilic substitution of N-[2-(hydroxymethyl)phenyl]pyrrole
Author(s)
Schlosser, Manfred ; Faigl, Ferenc
Published in
Tetrahedron
Volume
50
Issue
7
Pages
2071-6
Date
1994
ISSN
0040-4020
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
Note
CAN 120:270340
28-22
Heterocyclic Compounds (More Than One Hetero Atom)
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
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)
28-22
Heterocyclic Compounds (More Than One Hetero Atom)
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
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
LSCO
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > SB Archives > LSCO - Laboratory of Organic Synthesis and Catalysis
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Work produced at EPFL
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Published
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date
2006-03-03