Zur Kondensation von Carbonylverbindungen mit Hydrazinen, XIII: Über die Reaktion von Alkyl‐ und Aralkylhydrazinen mit Zuckern

Stroh, Hans‐Hartwig; Scharnow, Hans‐G.

doi:10.1002/cber.19650980535

Cited by 25 publications

(3 citation statements)

References 31 publications

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“…All reagents were purchased from commercial suppliers and used without further purification unless otherwise noted. Allylhydrazine (25d) [16] and hexylhydrazine (25b) [17] were prepared from the corresponding bromides and hydrazine. The (2-hydroxyethyl)hydrazine ( 2-hydrazinoethanol; 25c) was prepared as described [18] or purchased from Sigma-Aldrich.…”

Section: Experimental Partmentioning

confidence: 99%

Helicity‐Encoded Molecular Strands: Efficient Access by the Hydrazone Route and Structural Features

Schmitt¹,

Stadler²,

Kyritsakas³

et al. 2003

Helvetica Chimica Acta

113

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Dedicated to Professor Jack D. Dunitz on the occasion of his 80th birthday Control over the folding of molecular strands may be achieved by appropriate choice of the constituting subunits, in particular for chains of specific heterocycles such as sequences of directly connected pyridine (py) and pyrimidine (pym) rings, which are known to fold into extended helical structures. Since the hydrazone (hyz) group represents an isomorphic analogue of a py site, the condensation of hydrazine and carboxaldehyde derivatives of pym offers a very efficient approach to strands incorporating hyz instead of py units and constituted by sequences of alternating hyz and pym groups. A series of such strands of different lengths, up to ten hyz units, i.e., 1 ± 7, were synthesized. Their spectral properties indicate that they fold indeed into helical shapes. Extensive characterization was performed in solution by 1 H-NMR spectroscopy and in the solid state by determination of the crystal structures of eight such strands. They all display the expected helical geometry with up to 3 1 / 3 turns and direct stacking contacts. The efficiency and flexibility of the synthetic approach as well as its wide potential for generation of diversity through lateral decoration make the (hyzÀpym) subunit a particularly attractive helicity codon.Introduction. ± The design of molecular strands capable of taking up defined and predictable shapes is of much interest in view of its relation to biological folding processes in proteins as well as of the access it provides to the generation of welldefined geometries for functional devices and materials. Intense activity has recently been displayed in this area, implementing various types of supramolecular, noncovalent interactions (H-bonding, stacking and electrostatic interactions, metal-ion coordination) as well as medium effects, to induce the self-organization of a molecular strand into specific architectures [1]. A range of geometries from entirely helical to fully linear may thus be targetted.In our laboratories, we have made use of different interaction patterns and structuration subunits to generate single helices [2 ± 8]

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Section: Experimental Partmentioning

confidence: 99%

Helicity‐Encoded Molecular Strands: Efficient Access by the Hydrazone Route and Structural Features

Schmitt¹,

Stadler²,

Kyritsakas³

et al. 2003

Helvetica Chimica Acta

113

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show abstract

“…), 3.81 (s, 3 ), 6.17 (s, 1 H), 6.85 (br s, 2 H), 11.35 (br s, 1 H); NMR (CF3COOH) (isomer A) 2.49 (s, 3 H), 3.67 (s, 3 ), 4.12 (s, 3 H), 6.65 (s, 1 H); NMR (CF3COOH) (isomer B) 2.61 (s, 3 H), 3.67 (s, 3 ), 4.08 (s, 3 H), 6.56 (s, 1 H); UV Xmax (CH3OH) 240 nm (< 13 300), 290 (12 Reaction conditions for other hydrazones of methyl pyruvate: (starting hydrazinopyrimidine, molar ratio of the pyrimidine to methyl pyruvate, reaction medium, reflux time, yield).…”

Section: -Amino-4-methoxy-6-(l-methylhydrazino)pyrimidine (7c)mentioning

confidence: 99%

Pyrimido[4,5-c]pyridazines. 1. Cyclizations with .alpha.-keto esters

Morrison¹,

Mallory²,

Styles³

1978

J. Org. Chem.

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“…Hydrazones are readily formed by heating a lactol with a hydrazine in alcohol. − The acyclic hydrazone ( 1a ; 1 H NMR for H 1 , ca . δ 7) and a cyclic hydrazine isomer ( 1b ; 1 H NMR for H 1 , ca .…”

mentioning

confidence: 99%

Preparation of Aldehydo Sugars and Sugar Acids via Ozonolysis of Sugar Hydrazones

Spencer¹,

Yu²,

Cavallaro³

et al. 1997

J. Org. Chem.

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Zur Kondensation von Carbonylverbindungen mit Hydrazinen, XIII: Über die Reaktion von Alkyl‐ und Aralkylhydrazinen mit Zuckern

Cited by 25 publications

References 31 publications

Helicity‐Encoded Molecular Strands: Efficient Access by the Hydrazone Route and Structural Features

Helicity‐Encoded Molecular Strands: Efficient Access by the Hydrazone Route and Structural Features

Pyrimido[4,5-c]pyridazines. 1. Cyclizations with .alpha.-keto esters

Preparation of Aldehydo Sugars and Sugar Acids via Ozonolysis of Sugar Hydrazones

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