82215-92-7Relevant academic research and scientific papers
Improved and expanded one-pot, two-component Boulton-Katritzky syntheses of N–N bond containing bicyclic heterocycles
Knouse, Kyle W.,Ator, Laura E.,Beausoleil, Lauren E.,Hauseman, Zachary J.,Casaubon, Rebecca L.,Ott, Gregory R.
, p. 202 - 205 (2016/12/28)
Improved and expanded one-pot, two-component syntheses of bicyclic heterocycles containing a 3-N-acyl-3-amino-1,2-pyrazole motif from N'-hydroxy-carboxyamidines and acylbenzotriazoles have been developed. Importantly, this sequence obviates the need for h
Synthetic studies toward 3-(acylamino)-1 H-indazoles and development of a one-pot, microwave-assisted, oxadiazole condensation/Boulton-Katritzky rearrangement
Ott, Gregory R.,Anzalone, Andrew V.
, p. 3018 - 3022 (2012/01/05)
Studies on the Boulton-Katritzky rearrangement of 3-(2-aminoaryl)-1,2,4- oxadiazoles have led to the identification of additional electronic factors that govern the rearrangement as well as a competitive thermal rearrangement pathway for select substrates
N-(indazolyl)benzamido derivatives as CDK1 inhibitors: Design, synthesis, biological activity, and molecular docking studies
Raffa, Demetrio,Maggio, Benedetta,Cascioferro, Stella,Raimondi, Maria Valeria,Daidone, Giuseppe,Plescia, Salvatore,Schillaci, Domenico,Cusimano, Maria Grazia,Titone, Lucina,Colomba, Claudia,Tolomeo, Manlio
experimental part, p. 265 - 273 (2009/09/06)
A series of N-1H-indazole-1-carboxamides has been synthesized and their effects on both CDK1 / cyclin B and the K-562 (human chronic myelogenus leukemia) cell line were evaluated. Using a computational model, we have observed that all the most active compounds 9e, f, i-n exhibited the same binding mode of purvanalol A in the ATP-binding cleft. Although they were able to moderately inhibit the leukemic cell line K-562 and to show inhibitory activity against the Cdc2-Cyclin B kinase in the low micromolar range, they turned out to be non-cytotoxic against HuDe (IZSL) primary cell cultures from human derm. These preliminary results are quite encouraging in view of the low toxicity demonstrated by the above-mentioned compounds.
Photoinduced molecular rearrangements. The photochemistry of some 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles. Formation of 1,2,4-triazoles, indazoles, and benzimidazoles
Buscemi, Silvestre,Vivona, Nicolo,Caronna, Tullio
, p. 8397 - 8401 (2007/10/03)
The photochemistry of some 3,5-disubstituted 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles [external, such as added amines or hydrazines, or internal, such as an o-aminophenyl moiety at C(3) of the oxadiazole ring] has been investigated. In the irradiation of 5-amino-(or 5-N-substituted amino) 3-phenyl-1,2,4-oxadiazoles in the presence of aliphatic primary amines (or ammonia), photolytic species arising from heterolytic cleavage of the ring O-N bond capture the nucleophilic reagent to give open-chain intermediates, which develop into 1,2,4-triazolin-5-ones. Similarly, irradiations of 3,5-diphenyl-, 3-methoxy-5-phenyl-, and 5-methyl-3-phenyl-1,2,4-oxadiazoles gave 1,2,4-triazoles. In the same context, irradiations of representative substrates in the presence of hydrazines have been also investigated. In the irradiation of 3-(o-aminophenyl)-5-methyl-, 3-[o-(methylamino)phenyl]-5-methyl-, and 3-(o-aminophenyl)-5-phenyl-1,2,4-oxadiazoles, concomitant formation of indazoles and benzimidazoles, presumably arising from a common photolytic species, has been observed. Some mechanistic aspects have been considered, and possible applications in synthesis have been pointed out.
RECENT RESULTS ON THE CYCLIZATION TENDENCY OF DIACYL 2-AMINOBENZAMIDOXIMES
Korbonits, Dezsoe,Kolonits, Pal
, p. 795 - 802 (2007/10/02)
O,N-Diacyl derivatives of 2-aminobenzamidoxime transform, depending on the substitution and pH to quinazoline-3-oxides, 4-quinazolone-oximes, 1,2,4-oxadiazoles or 3-aminoindazoles. 1-Acyl-3-acylaminoindazoles can be selectively hydrolyzed in basic media t
pH Dependent Alternative Ring Closure of Monoacyl 2-Aminobenzamide Oximes. A New 2-Aminobenzimidazole Synthesis
Korbonits, Dezso,Kolonits, Pal
, p. 1652 - 1665 (2007/10/02)
N-Acyl and O-acyl derivatives of 2-aminobenzamide oxime (1) are versatile synthons to prepare different types of heterocycles by intramolecular condensations in which the two nitrogen atoms of the amide oxime moiety, the aromatic amino nitrogen and C-1 of
Ring Transformation of 3-(2-Aminoaryl)-1,2,4-oxadiazoles into 3-Acylaminoindazoles; Extension of the Boulton-Katritzky Scheme
Korbonits, Dezsoe,Kanzel-Szvoboda, Ida,Horvath, Karoly
, p. 759 - 766 (2007/10/02)
The ring transformation of 3-(2-aminoethyl)-1,2,4-oxadiazoles (1) into acylaminopyrazolines (2) reported earlier has been extended to 5-substituted 3-(2-aminoaryl)-1,2,4-oxadiazoles (3), (5), (7), and (9).Depending on the reaction conditions and the subst
