Über N<sup>β</sup>‐Cyan‐säurehydrazide und ihre Umwandlung in 1,2,4‐Triazolone‐3

Gehlen, Heinz

doi:10.1002/jlac.19495630203

Cited by 63 publications

(6 citation statements)

References 2 publications

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“…N'-Cyano-N,N'-dimethylhydrazides can be obtained by reaction of the corresponding N,N'-dimethylhydrazides with cyanogen bromide. Contrary to that, conversion of unsubstituted hydrazides leads to 2-amino-1,3,4-oxadiazoles by spontaneous cyclization of the intermediary cyanohydrazides [5,6], even though open-chain N,N'-unsubstituted cyanohydrazides have been reported erroneously in the earlier literature [7].…”

Section: Introductionmentioning

confidence: 79%

Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate

2012

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Abstract:The conversion of Z-phenylalanine hydrazide with cyanogen bromide resulted in the formation of the corresponding 2-amino-1,3,4-oxadiazole by spontaneous cyclization of the intermediary cyanohydrazide. The molecular structure of the product was confirmed by single crystal X-ray diffraction. Crystals of the title compound where obtained from a saturated solution in a mixture of petroleum ether and ethyl acetate and belong to the monoclinic space group P2 1 with unit cell parameters a = 9.8152(2) Å, b = 9.6305(2) Å, c = 9.8465(2) Å, β = 116.785(1)°. The asymmetric unit contains one molecule.

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Section: Introductionmentioning

confidence: 79%

Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate

2012

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“…The free bases 14 a ± c were isolated by washing 13 with aqueous Na 2 CO 3 . Similar reactions in solution gave compounds 14 a,c with only 81 % [12] and 35 % yield, respectively. [13] Cyanamides are very useful reagents for a multitude of intermolecular syntheses.…”

Section: Resultsmentioning

confidence: 98%

Quantitative Gas-Solid Reactions with ClCN and BrCN: Synthesis of Cyanamides, Cyanates, Thiocyanates, and Their Derivatives

1998

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Gas ± solid reaction techniques allow quantitative cyanations with ClCN and BrCN. Three primary and four secondary cyanamides, a cyanimide, four cyanates, and four thiocyanates were all prepared as solids in 100 % yield from solid anilines, benzimidazoles, imides, phenolates, and thiolates, respectively. Intramolecular solidstate reactions of cyanated o-aminophenol and of cyanated hydrazides gave heterocyclic compounds. When comparable reactions were performed in solution the reported product yields were considerably less than 100 % in all cases. The reasons for the success of the environmentally benign solid-state syntheses are discussed in terms of phase rebuilding, phase transformation, and crystal disintegration. Atomic force microscopy (AFM) of selected systems indicates the occurrence of long-range molecular movements which are governed by the crystal packing. This is evident from the obvious correlations between the molecular movements and the known crystal packing data. A new type of geometric surface feature, a rectangular and a rhombic depression which resembles a swimming-pool basin, was found in the cyanation of o-aminophenol and benzohydrazide.

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“…Additional examples included the synthesis of the 2-amino-1,3,4-oxadiazole analog (entry 9) [8], which was converted cleanly in excellent yield from benzoic hydrazide, and the synthesis of a fused ring compound with a nitrogen atom at the ring junction (entry 10) [9], from 2-pyridinehydrazine.…”

Section: Jan-feb 2003 191mentioning

confidence: 99%

Formation of nitrogen‐containing heterocycles using di(imidazole‐1‐yl)methanimine

Limburg

Wilkinson

et al. 2003

Journal of Heterocyclic Chem

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Über N^β‐Cyan‐säurehydrazide und ihre Umwandlung in 1,2,4‐Triazolone‐3

Abstract: 185 l'-Meth~l-5-oxy-6-met~~~l-5,6,7,8-tetrc~h~dro-l,2-~en~anthra~n (XIX)

Cited by 63 publications

References 2 publications

Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate

Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate

Quantitative Gas-Solid Reactions with ClCN and BrCN: Synthesis of Cyanamides, Cyanates, Thiocyanates, and Their Derivatives

Formation of nitrogen‐containing heterocycles using di(imidazole‐1‐yl)methanimine

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Über Nβ‐Cyan‐säurehydrazide und ihre Umwandlung in 1,2,4‐Triazolone‐3

Abstract: 185 l'-Meth~l-5-oxy-6-met~~~l-5,6,7,8-tetrc~h~dro-l,2-~en~anthra~n (XIX)

Cited by 63 publications

References 2 publications

Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate

Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate

Quantitative Gas-Solid Reactions with ClCN and BrCN: Synthesis of Cyanamides, Cyanates, Thiocyanates, and Their Derivatives

Formation of nitrogen‐containing heterocycles using di(imidazole‐1‐yl)methanimine

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Über N^β‐Cyan‐säurehydrazide und ihre Umwandlung in 1,2,4‐Triazolone‐3