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Synlett 2014; 25(1): 89-92
DOI: 10.1055/s-0033-1340111
letter
© Georg Thieme Verlag Stuttgart · New York

A Versatile Annulation Route to Primary-Amino-Substituted Naphthyridine Esters

Jinhua Chen
a   Wuxi AppTec, 288 Fute Zhong Road, Waigaoqiao Free Trade Zone, Shanghai 200131, P. R. of China
,
Zijin Xu
a   Wuxi AppTec, 288 Fute Zhong Road, Waigaoqiao Free Trade Zone, Shanghai 200131, P. R. of China
,
Tao Wang
a   Wuxi AppTec, 288 Fute Zhong Road, Waigaoqiao Free Trade Zone, Shanghai 200131, P. R. of China
,
Joseph P. Lyssikatos
b   Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA 94080, USA   Fax: +1(650)7424943   eMail: chudin@gene.com
,
Chudi O. Ndubaku*
b   Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA 94080, USA   Fax: +1(650)7424943   eMail: chudin@gene.com
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Publikationsverlauf

Received: 16. August 2013

Accepted after revision: 09. Oktober 2013

Publikationsdatum:
02. Dezember 2013 (online)

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Abstract

A straightforward four-step synthesis of primary-amino-substituted naphthyridine esters from commercially available cyano­pyridines was described. The route makes use of a condensation reaction between pyridinyl acetates with N,N-dimethylformamide dimethylacetal (DMF-DMA) to form ortho-cyano vinylogous carbamates. These intermediates can undergo facile cyclization with ammonium acetate in acetic acid to generate the corresponding naphthyridine esters in good synthetic yields. The synthesis of ­primary-amino-substituted 7-azaquinoxaline was also described.

Key words

naphthyridine - annulation - vinylogous carbamates - heterocycles - scaffold
 

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