Simple and Efficient Synthesis of 2,7-Difunctionalized-1,8-Naphthyridines 英文参考文献.docVIP

Molecules 2005, 10, 929-936 molecules ISSN 1420-3049 Simple and Efficient Synthesis of 2,7-Difunctionalized-1,8- Naphthyridines Shyamaprosad Goswami *, Reshmi Mukherjee, Rakhi Mukherjee, Subrata Jana, Annada C. Maity, and Avijit Kumar Adak Department of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah-711 103, West Bengal, India. Fax: (+91)-33 * Author to whom correspondence should be addressed. E-mail: spgoswamical@ Received: 25 August 2004; in revised form: 23 November 2004 / Accepted: 6 January 2005 / Published: 31 August 2005 Abstract: The syntheses in good yields of some new difunctionalized 1,8-naphthyridines 4, 6, 8 and 9 and a novel triethylene glycol ether-linked dinaphthyridine, 10a, along with the mononaphthyridine-linked ether alcohol 10b are described. An improved and milder method for the synthesis of 2,7-diamino-1,8-naphthyridine (14) is also reported. Keywords: Naphthyridines, 2,7-difunctionalized-1,8-naphthyridines, 2,7-diamino-1,8- naphthyridine. Introduction Naphthyridine or naphthyridone systems are of great importance due to their broad spectrum of biological activities. Substituted 1,8-naphthyridine compounds are used as antihypertensives, antiarrhythmics, herbicide safeners and also as immunostimulants [1-3]. We are interested in 2,7-difunctionalized-1,8-naphthyridines because of their aforesaid potential medicinal activity as well as for their use as important binding units in the molecular design of synthetic receptors [4]. This communication describes the first synthesis of four 2,7-difunctionalized-1,8-naphthyridines; viz. 2- amino-7-hydroxymethyl-1,8-naphthyridine (5), 2-amino-1,8-naphthyridine-7-carboxaldehyde (6), 2,7- dimethyl-4-methoxy-1,8-naphthyridine (8) and 4-methoxy-1,8-naphthyridine-2,7-dicarboxaldehyde (9) and a novel triethylene glycol ether-linked dinaphthyridine compound, 1,2-bis-[2-(2,7-dimethyl-1,8- naphthy