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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 24期

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.

引用

页码：6625 / 6628

页数：4

共 27 条

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