Tandem Ugi MCR/Mitsunobu Cyclization as a Short, Protecting-Group-Free Route to Benzoxazinones with Four Diversity Points

被引：50

作者：

Banfi, Luca ^{[1
]}

Basso, Andrea ^{[1
]}

Giardini, Lorenzo ^{[1
]}

Riva, Renata ^{[1
]}

Rocca, Valeria ^{[1
]}

Guanti, Giuseppe ^{[1
]}

机构：

[1] Univ Genoa, Dept Chem & Ind Chem, I-16146 Genoa, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 01期

关键词：

Multicomponent reactions; Nucleophilic substitution; Isocyanides; Oxygen heterocycles; Combinatorial chemistry; REACTION/RING-CLOSING METATHESIS; MULTICOMPONENT SYNTHESIS; 1,4-BENZOXAZINE; HETEROCYCLES; DERIVATIVES; ANTAGONISTS; MITSUNOBU; LIBRARY; DESIGN;

D O I：

10.1002/ejoc.201001077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem Ugi/Mitsunobu protocol, starting from o-aminophenols, alpha-hydroxy acids, amines and aldehydes gives benzo[b][1,4]oxazin-3-ones of general formula 1 in two high-yielding steps, with the introduction of up to four diversity inputs. The mildness of the methodology allows the stereospecific synthesis of enantiomerically pure products as well as the introduction of additional functional groups. The overall procedure can also be carried out in a one-pot manner.

引用

页码：100 / 109

页数：10

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