TY - JOUR
T1 - Convenient Synthesis of 2-Amino-1,8-naphthyridines, Building Blocks for Host-Guest and Self-Assembling Systems
AU - Fenlon, Edward E.
AU - Murray, Thomas J.
AU - Baloga, Monica H.
AU - Zimmerman, Steven C.
PY - 1993/1/1
Y1 - 1993/1/1
N2 - 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 Friedländer 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.
AB - 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 Friedländer 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.
UR - http://www.scopus.com/inward/record.url?scp=0027743322&partnerID=8YFLogxK
U2 - 10.1021/jo00076a021
DO - 10.1021/jo00076a021
M3 - Article
AN - SCOPUS:0027743322
SN - 0022-3263
VL - 58
SP - 6625
EP - 6628
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -