COMBINED DIRECTED METALATION - SUZUKI-MIYAURA CROSS COUPLING STRATEGIES. SYNTHESIS OF ISOMERIC CHROMENOPYRIDINONES and RELATED ANNULATED ANALOGUES

被引：6
|
作者：
Miller, Ricarda E. [1 ,2 ]
Sommer, Roman [1 ,2 ]
Fan, Hope [1 ,2 ]
Snieckus, Victor [3 ]
Groth, Ulrich [1 ,2 ]
机构：
[1] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany
[2] Univ Konstanz, Konstanz Res Sch Chem Biol, D-78457 Constance, Germany
[3] Queens Univ, Kingston, ON K7L 3N6, Canada
来源：
HETEROCYCLES | 2012年 / 86卷 / 02期
基金：
加拿大自然科学与工程研究理事会;
关键词：
Combined Directed Metalation; Suzuki-Miyaura Cross-Coupling; Chromenopyridinone; REGIOSELECTIVE ORTHO-LITHIATION; REMOTE-METALATION;
D O I：
10.3987/COM-12-S(N)131
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general strategy encompassing a Directed ortho Metalation (DoM) - Suzuki-Miyaura cross coupling and Directed remote Metalation (DreM) sequence for the synthesis of 5H-chromeno[4,3-c]pyridin-5-ones 5a-j, 5H-chromeno[3,4-b]pyridin-5-ones 6a-j, 5H-chromeno[3,4-c]pyridin-5-ones 13a-d, 12H-benzo[7,8]chromenopyridin-12-ones 16a-c, 17a-c, and pyrido[31,41:4,5]pyrano[2,3-e]indazol-5(111)-one analogues 18, 28 is reported. Thus, using the powerful directed metalation group properties of aryl O-carbamates 9a-h, 14a-c metalation-boronation followed by Suzuki-Miyaura coupling with 3-bromopyridine affords a variety of azabiaryls 7a-i, 8a-b, 12a-c, 15a-c which, upon DreM reaction leads to several series of chromenopyridinones 5a-j, 6a-j, 13a-d and pyridonaphthopyrones 16a-c, 17a-c. The synthesis of an unusual pyridopyranoindazolone 18 is also described.
引用
收藏
页码：1045 / 1054
页数：10
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