CONVENIENT SYNTHESIS OF 2-AMINO-1,8-NAPHTHYRIDINES, BUILDING-BLOCKS FOR HOST-GUEST AND SELF-ASSEMBLING SYSTEMS

被引:58
作者
FENLON, EE [1 ]
MURRAY, TJ [1 ]
BALOGA, MH [1 ]
ZIMMERMAN, SC [1 ]
机构
[1] UNIV ILLINOIS,DEPT CHEM,ROGER ADAMS LAB 354,BOX 35,600 S MATHEWS AVE,URBANA,IL 61801
关键词
D O I
10.1021/jo00076a021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Application of the Reimer-Tiemann reaction to 2,6-diaminopyridine afforded a 26% yield of 2,6-diaminopyridine-3-carboxaldehyde (4) and a small amount (4%) of 2,6-diaminopyridine-3,5-dicarboxaldehyde. Alternatively, conversion of 2,6-diaminopyridine to 2,6-bis(pivaloylamino)pyridine (6), directed lithiation with n-butyllithium, treatment with N-formylmorpholine, and hydrolysis produced 4 in 67% overall yield. The Friedlander condensation of 4 with a variety of activated and unactivated ketones afforded 2-amino-1,8-naphthyridines and bis(2-amino-1,8-naphthyridines) in moderate to good yields, providing a convenient synthesis of useful building blocks for new host-guest and self-assembling systems.
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页码:6625 / 6628
页数:4
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