Convenient synthesis of 2-amino-1,8-naphthyridines, building blocks for host-guest and self-assembling systems

Association constants of 2,6-bis(alkylcarbonylamino)pyridines (alkyl = methyl or ethyl) and their perfluoroalkyl analogues with succin-and maleimide as well as with 2,2 0 -dipyridylamine (complementary DAD and ADA hydrogen bonding motifs are responsible for formation of the associates) have been determined by NMR titrations and quantum chemical calculations. Interactions of 2,6-bis (alkylcarbonylamino)pyridines with imides differ by character from these of perfluoroalkyl analogues. Such large difference was not observed for the 2,2 0 -dipyridylamine associates. Since fluorine atoms cause carbonylamino groups to be stronger hydrogen bond donors, perfluorinated species of this type were found to be more stable. Single crystal X-ray structures of 2,6-bis(trifluoromethylcarbonylamino)pyridine and 2,6-bis(pentafluoroethylcarbonylamino)pyridine have been also determined.

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“…6. It is noteworthy that K assoc obtained now are comparable to these for other triple hydrogen-bonded systems [44,[50][51][52].…”

Section: Nmrsupporting

confidence: 72%

NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

et al. 2010

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“…[15,16] The reaction with malonamidonitriles according to the preparation of Fenlon affords the 2-aminonaphthyridine-3-carboxamides (Scheme 3). [17] Scheme 3. Synthesis and binding sites (in italics) of the 2-amino-…”

Section: Resultsmentioning

confidence: 99%

Formation of Gel-Like Systems of an 2,6,8,12,14,18,20,24-Octahydroxypyridine[4]arene and an 2-Aminonaphthyridine

et al. 2002

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Keywords: Calixarenes / Gels / Hydrogen bonds / Aggregation / Supramolecular chemistry 2,6,8,12,14,18,20,arenes are capable of forming complexes with suitable partner molecules. In apolar media the formation of gel-like aggregates of an octahydroxypyridine[4]arene and an 2-aminonaphthyridine at a ratio of 1:4 was observed. This viscous liquid was investigated by means of rheology and TEM techniques and was

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“…[15] The 2,6-diaminopyridine-3-carbaldehyde (21) starting material was prepared by literature procedures. [25] Condensation with cyanoacetamides gave the naphthyridines 23. [26] The amino acid derived cyanoacetamide 20 was prepared from lysine as shown in Scheme 3.…”

Section: Syntheses Of Daad Moleculesmentioning

confidence: 99%

“…2,6-Diaminopyridine-3-carbaldehyde [25] (21, 1.57 g, 11.5 mmol), cyanoacetamide (22a, 19.3 g, 230 mmol) and piperidine (5 mL) were dissolved under nitrogen in dry ethanol (150 mL) and heated to reflux for 3.5 h. After removal of the solvent, the residue was partitioned between 150 mL of water and 150 mL of dichloromethane. The layers were separated and the yellow solid at the interface between the layers was filtered off.…”

Section: 7-diamino-18-naphthyridine-3-carboxamide (23a)mentioning

confidence: 99%

Four Hydrogen Bonds − DDAA, DADA, DAAD and ADDA Hydrogen Bond Motifs

Lüning

Kühl²,

Uphoff

2002

Eur. J. Org. Chem.

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Receptor molecules containing four hydrogen-bond acceptor or donor sites based on aminopyridines, aminonaphthyridines and urea subunits have been synthesized and their association has been investigated. DDAA (13a−c) and DADA (18a−b) arrays may form homodimers, while DAAD (24a−d) with ADDA (25a−b) may form heterodimers. While most parent heterocycles were only slightly soluble in standard organic solvents, substitution was able to enhance the solubility in most cases. The naphthyridine 24d, bearing a substituMultiple hydrogen bonds can be found in many recognition processes, both in enzymes and in the genetic code. [1] Correct binding by two or three parallel [2] or antiparallel hydrogen bonds is the key feature of the genetic code, which uses substituted purines and pyrimidines for the recognition and the storage of genetic information. [3] The number of hydrogen bonds involved in a recognition event has two important influences on the quality of this process: (i) the more hydrogen bonds are involved in a recognition, the tighter the binding usually becomes, [4Ϫ7] and (ii) more hydrogen bonds can convey more information.A hydrogen bond between a hydrogen-bond donor (D) and a hydrogen-bond acceptor (A) possesses a direction. Therefore, with two hydrogen bonds, two different pairs, formed from three different molecules, are possible: a heterodimer in which a DD unit binds AA, and a homodimer made of two DA molecules. Addition of one more hydrogen bond results in three possible dimers formed by six different units: DDD·AAA, DDA·AAD and DAD·ADA. With four hydrogen bonds, ten different molecules and six different dimers are possible (see Figure 1).In addition to the stronger binding due to the four hydrogen bonds in these dimers, more information can be stored [ ‡] Multiple hydrogen bonds, 3. Part 2 Ref. [33] [a]

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Convenient synthesis of 2-amino-1,8-naphthyridines, building blocks for host-guest and self-assembling systems

Cited by 64 publications

References 2 publications

NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

Formation of Gel-Like Systems of an 2,6,8,12,14,18,20,24-Octahydroxypyridine[4]arene and an 2-Aminonaphthyridine

Four Hydrogen Bonds − DDAA, DADA, DAAD and ADDA Hydrogen Bond Motifs

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