Synthesis of various substituted dibenzo[b,d]pyranones including amino acid derivatives by SRN1 methodology
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)]
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Beugelmans, R., Bois-Choussy, M., Chastanet, J., Le Gleuher, M., & Zhu, J. (1993). Synthesis of various substituted dibenzo[b,d]pyranones including amino acid derivatives by SRN1 methodology. Heterocycles, 36(12), 2733–2732. https://doi.org/10.3987/COM-93-6494
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1993
36
12
2733
32
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)
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