One-Pot Synthesis of Dibenz[b,f][1,4]oxazepines via Mg(ClO₄)₂-Catalyzed Ugi Four-Component Reaction and Microwave-Assisted Intramolecular S_NAr

• Autorzy: Jialu Luo , Jinlong Wu , Wei-Min Dai
• Języki publikacji: EN

Abstrakty

EN

A general one-pot synthesis of dibenz[b,f][1,4] oxazepine-11(10H)-carboxamides is described. The Ugi four-component reaction (U-4CR) of 2-aminophenols, cyclohexyl isocyanide, 2-chloro-5-nitrobenzaldehyde, and 2-bromobenzoic acids in MeOH in the presence of 25 mol% Mg(ClO4)2 at 30-40 .C for 22-95 h gave the linear Ugi products. The latter were treated with aqueous K2CO3 in MeOH under microwave heating at 120 .C for 10 min for promoting the intramolecular nucleophilic aromatic substitution (SNAr), affording the 6/7/6-fused tricyclic heterocycles in 61-85% yields.

Słowa kluczowe

EN

dibenz[b,f][1,4]oxazepine; Lewis acid; microwave; multicomponent reactions; nucleophilic aromatic substitutions

• Czasopismo: Diversity Oriented Synthesis
• Rocznik: 2012
• Tom: 1
• Numer: 1

Daty

otrzymano

2014-05-17

zaakceptowano

2014-06-20

online

2014-07-08

Twórcy

autor

Jialu Luo

• Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China

autor

Jinlong Wu

• Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China

autor

Wei-Min Dai

• Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China

Bibliografia

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Identyfikatory

DOI

10.2478/dos-2014-0001