3-Substituted amino-4,5-disubstituted 1,2,4-4H-triazole and aldehyde from 1-acyl semicarbazide

Dutta, Sakti P.; Das, Bijan; Paul, Birendra Kumar; Acharyya, Auditi K.; Basu, U.

doi:10.1021/jo01266a088

Cited by 6 publications

(1 citation statement)

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“…225 °C (dec)]. 16 Single crystals were obtained from ethanol solutions by slow evaporation at room temperature. All of the single crystals used in the X-ray analyses were observed, on heating, using a polarizing microscope, and no evidence of solid-solid transition was detected prior to melting.…”

Section: Synthesismentioning

confidence: 99%

Orthogonal H-bonding synthons, actual and virtual structures in molecular crystals: a case study

et al. 2014

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Semicarbazides of p-substituted benzoic acids are a class of simple molecules endowed with H-bonding donor and acceptor groups capable of forming H-bonded rows along three linearly independent directions (orthogonal H-bonding synthons). When the acceptor group at the para position is strong (–NO2, –CN, –N=) the same crystal packing is observed, in which three linearly independent chains are formed, and the lattice parameters are easily predictable. In the case of halogen atoms at the para position (–F, –Cl) two different packings are observed in which only one or two H-bonded chains are present. Through ab initio periodic DFT-LCAO computations, we have calculated the lattice energy and density of each semicarbazide in each of the three packings, constructing the matrices Uij and ρij of the lattice energy and density. It is found that all of the different modes of packing observed experimentally for single members of the class correspond to minima of the lattice energy and to acceptable lattice densities for every member of the class

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Section: Synthesismentioning

confidence: 99%

Orthogonal H-bonding synthons, actual and virtual structures in molecular crystals: a case study

et al. 2014

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Chemical Abstract and Journal References for 1,2,4‐Triazoles

1981

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Ring‐opening reaction of 1,3,4‐oxadiazolone and 1,3,4‐oxadiazolinethione: Reaction of 2‐phenyl‐1,3,4‐oxadiazolin‐5‐one and 2‐phenyl‐1,3,4‐oxadiazoline‐5‐thione with amines

Saegusa

Harada

Nakamura

1988

Journal of Heterocyclic Chem

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The ring‐opening abilities of amines toward 1,3,4‐oxadiazolines, 2‐phenyl‐1,3,4‐oxadiazolin‐5‐one (1a) and 2‐phenyl‐1,3,4‐oxadiazoline‐5‐thione (1b), were investigated with relation to their basicities or pKb values. Oxadiazolines 1a and 1b were easily reacted with amines such as benzylamine and aniline, but not with p‐nitroaniline, to form the corresponding ring‐opening adducts. The reactions of both 1a and 1b with o‐phenylenediamine produced benzodiazoles with the liberation of benzoylhydrazide, whereas the reactions with o‐aminobenzamide furnished quinazolines with the liberation of ammonia. o‐Aminophenol and o‐aminothiophenol were also reacted with 1a and 1b both of them giving 1,5‐dibenzoylcarbohydrazide from 1a and 1,2‐dibenzoylhydrazine from 1b. From the conditions affording the corresponding ring‐opening adducts or reaction products, the ring‐opening abilities of the amines toward 1a and 1b are in good correlation with the strength of their basicities or pKb values. The ring‐opening of oxadiazolines were proved to occur with anilines. Therefore, the other reactions are also supposed to proceed via the ring‐opening steps.

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3-Substituted amino-4,5-disubstituted 1,2,4-4H-triazole and aldehyde from 1-acyl semicarbazide

Cited by 6 publications

References 0 publications

Orthogonal H-bonding synthons, actual and virtual structures in molecular crystals: a case study

Orthogonal H-bonding synthons, actual and virtual structures in molecular crystals: a case study

Chemical Abstract and Journal References for 1,2,4‐Triazoles

Ring‐opening reaction of 1,3,4‐oxadiazolone and 1,3,4‐oxadiazolinethione: Reaction of 2‐phenyl‐1,3,4‐oxadiazolin‐5‐one and 2‐phenyl‐1,3,4‐oxadiazoline‐5‐thione with amines

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