101630-94-8Relevant articles and documents
Convenient Synthesis of 2-Amino-1,8-naphthyridines, Building Blocks for Host-Guest and Self-Assembling Systems
Fenlon, Edward E.,Murray, Thomas J.,Baloga, Monica H.,Zimmerman, Steven C.
, p. 6625 - 6628 (1993)
Application of the Reimer-Tiemann reaction to 2,6-diaminopyridine afforded a 26percent yield of 2,6-diaminopyridine-3-carboxaldehyde (4) and a small amount (4percent) 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 percent overall yield.The Friedlaender 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.
Independently Tuned Frontier Orbital Energy Levels of 1,3,4,6,9b-Pentaazaphenalene Derivatives by the Conjugation Effect
Watanabe, Hiroyuki,Tanaka, Kazuo,Chujo, Yoshiki
, p. 2768 - 2778 (2019/02/26)
Herein reported are syntheses and the unique substituent effect in 1,3,4,6,9b-pentaazaphenalene (5AP) derivatives. We developed the new synthetic route via (N,N-pyridine-2,6-diyl)bisamides, which enabled us to prepare a variety of substituted 5APs and to
Understanding the effects of preorganization, rigidity, and steric interactions in synthetic barbiturate receptors
McGrath, Jacqueline M.,Pluth, Michael D.
, p. 711 - 719 (2014/04/03)
Synthetic barbiturate receptors have been utilized for many applications due to their high binding affinities for complementary guests. Although interest in this class of receptors spans from supramolecular to materials chemistry, the effects of receptor steric bulk and preorganization on guest binding affinity has not been studied systematically. To investigate the roles that steric bulk and preorganization play in guest binding, we prepared a series of 12 deconstructed Hamilton receptors with varying degrees of steric bulk and preorganization. Both diethylbarbital and 3-methyl- 7-propylxanthine were investigated as guests for the synthetic receptors. The stoichiometry of guest binding was investigated using Job plots for each host-guest pair, and 1H NMR titrations were performed to measure the guest binding affinities. To complement the solution-state studies, DFT calculations at the B3LYP/6-31+G(d,p) level of theory employing the IEF-PCM CHCl3 solvation model were also performed. Calculated guest binding energies correlated well with the experimental findings and provided additional insight into the factors influencing guest binding. Taken together, the results presented highlight the interplay between preorganization and steric interactions in establishing favorable interactions for self-assembled hydrogenbonded systems.