88229-19-0Relevant academic research and scientific papers
Crystal structure of 1-(2,4,6-trichlorobenzoyloxy) benzotriazole (TCB-OBt): observation of uncommon intermolecular oxygen-oxygen interaction and synthetic application in amidation
Dolai, Gobinda,Giri, Rajat Subhra,Mandal, Bhubaneswar,Roy, Sayanta,Sen, Srijit
, p. 19804 - 19811 (2021/11/12)
Herein, we investigated the supramolecular assembly of a modified Yamaguchi reagent TCB-OBt. Interestingly, each molecule is interconnected through novel chalcogen-chalcogen (O?O) interaction, π-π stacking, and aromatic C-H?O interaction. Hirshfeld surface analysis confirmed the existence of uncommon O?O interactions. A well-organized supramolecular layer structure and helical arrangement were observed in the crystal structure. TCB-OBt crystallized in the O-substituted desmotropic form. DFT calculations suggest that the O-substituted form is more stable than theN-substituted form (TCB-(N)-OBt). Morphology analysis indicates the formation of a fantastically well organized, continuous block-shaped system. Furthermore, the designed reagent works as an efficient activating reagent for amide bond formation with good yields under mild reaction conditions. Use of this reagent avoided intractable acid chlorides, and this new mixed-anhydride-based reagent may further be applicable for many other organic transformations.
Nematicidal activities of diamides with diphenylacetylene scaffold against Meloidogyne Incognita
Li, Jiling,Zhang, Zhicheng,Xu, Xiaoyong,Shao, Xusheng,Li, Zhong
, p. 1543 - 1549 (2015/10/20)
With the goal of searching for new potential nematicides with high activity and low toxicity, new molecules are needed as potential prototypes for the synthesis of new nematicidal compounds. A series of novel diamides based on diphenylacetylene scaffold were designed and synthesised. The conformation of the amide was restricted through the ten-membered H-bonded ring. Their structures were characterised by 1H NMR, 13C NMR, 19F NMR, and high-resolution mass spectrometry. The preliminary bioassays evaluated against Meloidogyne Incognita indicated that most of the title compounds were endowed with moderate-to-good activities at the concentration of 25mgL-1. In particular, compounds 9a, 9c, 9g, 9h, 9k, and 9l displayed >50% nematicidal activity at 5mgL-1. It is possible that the novel diamides with diphenylacetylene scaffold, which possess good nematicidal activities, provide distinct nematicidal chemotypes that can be used as leads for further optimisation.
Palladium-catalyzed ring-opening of cyclopropyl benzamides: Synthesis of benzo[c]azepine-1-ones via C(sp3)-H functionalization
Ladd, Carolyn L.,Roman, Daniela Sustac,Charette, André B.
, p. 4479 - 4487 (2013/06/26)
A variety of difficult to obtain benzo[c]azepine-1-ones are synthesized via a novel palladium-catalyzed, silver-promoted intramolecular cyclization of cyclopropyl benzamides. This biologically important class of molecules is prepared in an efficient and high-yielding manner from easily accessible starting materials. Both aryl bromides and iodides are effective substrates for the transformation. Mechanistic studies indicate that the reaction proceeds through a cyclopropyl C(sp3)-H cleavage step, followed by ring-opening, deprotonation, and reductive elimination.
POTENTIAL CENTRAL NERVOUS SYSTEM ACTIVE AGENTS. 3. SYNTHESIS OF SOME SUBSTITUTED BENZAMIDES AND PHENYLACETAMIDES.
Agwada
, p. 231 - 235 (2007/10/02)
The preparation and special properties (IR, **1H NMR) are given for 45 benzamides and 10 phenylacetamides substituted on nitrogen with allyl, benzhydryl, benzyl, or cyclopropyl groups, and variously substituted on the acyl part with halo, methoxyl, methyl, or nitro groups. The benzamide derivatives were synthesized by the Schotten-Baumann method, and the phenylacetamide derivatives were prepared by heating the appropriate N-benzhydrylammonium salt in o-xylene. Thirty-one of the compounds are new.
