Synthesis of various substituted dibenzo[b,d]pyranones including amino acid derivatives by SRN1 methodology
1993
Abstract
An easy prepn. of the title compds. involving a SRN1 o-arylation of phenolates by o-bromobenzonitrile followed by SiO2-catalyzed lactonization is described. Activated or not activated phenols are efficient. Access to benzonaphthopyranones is exemplified by the reactions with 2-naphtholate. Reactions with chiral p-hydroxyphenylamino acid derivs. are also reported. Thus, irradn. of Ac-L-Tyr(Ac)-OMe and 2-bromo-4,5-dimethoxybenzonitrile in liq. NH3, followed by treatment with silica in CH2Cl2, gave 52% dibenzopyranyl amino ester I. [on SciFinder (R)]
Details
Title
Synthesis of various substituted dibenzo[b,d]pyranones including amino acid derivatives by SRN1 methodology
Author(s)
Beugelmans, Rene ; Bois-Choussy, Michele ; Chastanet, Jacqueline ; Le Gleuher, Martine ; Zhu, Jieping
Published in
Heterocycles
Volume
36
Issue
12
Pages
2733-32
Date
1993
ISSN
0385-5414
Keywords
Amino acids Role: SPN (Synthetic preparation); PREP (Preparation) (dibenzopyranyl; prepn. via nucleophilic radical arom substitution reactions of phenol derivs. with bromobenzonitriles and silica-catalyzed cyclization); Cyclocondensation reaction (nucleophilic radical arom substitution reactions and; of bromobenzonitriles with phenols and naphthols to dibenzopyranones); Phenols Role: RCT (Reactant); RACT (Reactant or reagent) (nucleophilic radical arom substitution reactions with bromobenzonitriles and silica-catalyzed cyclization to dibenzopyranones); Substitution reaction (homolytic; of bromobenzonitriles with phenols and naphthols; and silica-catalyzed cyclization to dibenzopyranones); nucleophilic radical arom substitution phenolate; lactonization cyanophenylphenol; phenol cyanophenyl lactonization; dibenzopyranone; amino acid dibenzopyranylmethyl
Note
CAN 120:245721
34-2
Amino Acids, Peptides, and Proteins
Inst. Chim. Subs. Nat.,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
100-02-7 (4-Nitrophenol) Role: RCT (Reactant), RACT (Reactant or reagent) (attempted nucleophilic radical arom substitution reactions with bromobenzonitrile); 135-19-3 (2-Naphthol) Role: RCT (Reactant), RACT (Reactant or reagent) (nucleophilic radical arom substitution reactions with bromobenzonitriles); 96-76-4 (2,4-Di-tert-butylphenol); 98-54-4 (4-tert-Butylphenol); 371-41-5 (4-Fluorophenol); 767-00-0 (4-Hydroxybenzonitrile); 828-27-3 (4-(Trifluoromethoxy)phenol); 2033-89-8 (3,4-Dimethoxyphenol); 35068-04-3 (N,O-Diacetyltyrosine methyl ester); 143674-61-7 Role: RCT (Reactant), RACT (Reactant or reagent) (nucleophilic radical arom substitution reactions with bromobenzonitriles and silica-catalyzed cyclization to dibenzopyranones); 78247-62-8 Role: RCT (Reactant), RACT (Reactant or reagent) (nucleophilic radical arom substitution reactions with bromobenzonitriles and silica-catalyzed cyclization to dibenzopyranones, racemization in); 2042-37-7 (2-Bromobenzonitrile); 109305-98-8 (2-Bromo-4,5-dimethoxybenzonitrile) Role: RCT (Reactant), RACT (Reactant or reagent) (nucleophilic radical arom substitution reactions with phenol and naphthol derivs. and silica-catalyzed cyclization to dibenzopyranones); 154145-18-3P; 154145-19-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and silica-catalyzed cyclization to dibenzopyranone); 100540-63-4P; 101438-97-5P (5H-Benzo[d]naphtho[2,1-b]pyran-5-one); 108012-00-6P; 151648-57-6P; 151648-58-7P; 151648-59-8P (5H-Benzo[d]naphtho[2,3-b]pyran-5-one); 154145-15-0P; 154145-16-1P; 154145-17-2P; 154145-20-7P; 154145-21-8P; 154145-22-9P; 154145-23-0P; 154145-24-1P; 154145-25-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
34-2
Amino Acids, Peptides, and Proteins
Inst. Chim. Subs. Nat.,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
100-02-7 (4-Nitrophenol) Role: RCT (Reactant), RACT (Reactant or reagent) (attempted nucleophilic radical arom substitution reactions with bromobenzonitrile); 135-19-3 (2-Naphthol) Role: RCT (Reactant), RACT (Reactant or reagent) (nucleophilic radical arom substitution reactions with bromobenzonitriles); 96-76-4 (2,4-Di-tert-butylphenol); 98-54-4 (4-tert-Butylphenol); 371-41-5 (4-Fluorophenol); 767-00-0 (4-Hydroxybenzonitrile); 828-27-3 (4-(Trifluoromethoxy)phenol); 2033-89-8 (3,4-Dimethoxyphenol); 35068-04-3 (N,O-Diacetyltyrosine methyl ester); 143674-61-7 Role: RCT (Reactant), RACT (Reactant or reagent) (nucleophilic radical arom substitution reactions with bromobenzonitriles and silica-catalyzed cyclization to dibenzopyranones); 78247-62-8 Role: RCT (Reactant), RACT (Reactant or reagent) (nucleophilic radical arom substitution reactions with bromobenzonitriles and silica-catalyzed cyclization to dibenzopyranones, racemization in); 2042-37-7 (2-Bromobenzonitrile); 109305-98-8 (2-Bromo-4,5-dimethoxybenzonitrile) Role: RCT (Reactant), RACT (Reactant or reagent) (nucleophilic radical arom substitution reactions with phenol and naphthol derivs. and silica-catalyzed cyclization to dibenzopyranones); 154145-18-3P; 154145-19-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and silica-catalyzed cyclization to dibenzopyranone); 100540-63-4P; 101438-97-5P (5H-Benzo[d]naphtho[2,1-b]pyran-5-one); 108012-00-6P; 151648-57-6P; 151648-58-7P; 151648-59-8P (5H-Benzo[d]naphtho[2,3-b]pyran-5-one); 154145-15-0P; 154145-16-1P; 154145-17-2P; 154145-20-7P; 154145-21-8P; 154145-22-9P; 154145-23-0P; 154145-24-1P; 154145-25-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
Laboratories
LSPN
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Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
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Record creation date
2010-11-25