- Crystal structure of 1-(2,4,6-trichlorobenzoyloxy) benzotriazole (TCB-OBt): observation of uncommon intermolecular oxygen-oxygen interaction and synthetic application in amidation
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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.
- Dolai, Gobinda,Giri, Rajat Subhra,Mandal, Bhubaneswar,Roy, Sayanta,Sen, Srijit
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p. 19804 - 19811
(2021/11/12)
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- Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis
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The selective rearrangement of oxaziridines to amidesviaa single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis. The developed method shows excellent functional group tolerance with a broad substrate scope and good to excellent yields. Furthermore, control experiments and density functional theory (DFT) calculations are performed to gain insight into the reactivity and selectivity.
- Park, Jin,Park, Sehoon,Jang, Gwang Seok,Kim, Ran Hui,Jung, Jaehoon,Woo, Sang Kook
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p. 9995 - 9998
(2021/10/06)
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- Aminocarbonylation of Aryl Tosylates to Carboxamides
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The palladium - catalyzed aminocarbonylation of aryl tosylates with amines is reported. Suitable conditions were identified by high throughput reaction screening and then further optimized. The substrate scope of the reaction with respect to the aryl tosylate component and the amine component are reported. Competitive aminolysis of the aryl tosylates to afford the amine toluenesulfonamides and the phenol was not observed.
- Chung, Seungwon,Sach, Neal,Choi, Chulho,Yang, Xiaojing,Drozda, Susan E.,Singer, Robert A.,Wright, Stephen W.
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supporting information
p. 2848 - 2851
(2015/06/16)
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- Highly chemoselective rearrangement of 3-aryloxaziridines to nitrones or amides
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An efficient method for the chemoselective ring-opening rearrangement of 3-aryloxaziridines by using silver triflate alone to afford nitrones, or in the presence of a simple Br0nsted acid to yield amides, has been developed. Silver triflate plays an impor
- Xing, Dong,Xu, Xinfang,Yang, Liping
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experimental part
p. 3399 - 3404
(2010/02/28)
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- Synthesis of ortho-alkoxy-aryl carboxamides via alladium-catalyzed aminocarbonylation
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Various aryl carboxamides with alkoxy substituents at the ortho-position, applicable as direct intermediates toward novel ligands, were synthesised via aminocarbonylation of aryl-iodides (2-iodoanisole, 5-chloro-7-iodo-8-methoxy- quinoline, and 5-chloro-7-iodo-8-benzyloxy-quinoline) in the presence of in situ generated palladium(0) catalysts. Simple primary and secondary amines as well as aminoacid esters were used as N-nucleophiles. The optimization of the reaction conditions allowed the preferential formation of carboxamides or ketocarboxamides by simple or double carbon monoxide insertion, respectively. A strong dependence of the chemoselectivity on carbon monoxide pressure was observed. Copyright Taylor & Francis Group, LLC.
- Takacs, Attila,Abreu, Artur R.,Peixoto, Andreia F.,Pereira, Mariette,Kollar, Laszlo
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experimental part
p. 1534 - 1548
(2009/10/17)
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- An efficient and scalable ritter reaction for the synthesis of tert-butyl amides
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A scalable procedure for the conversion of nitriles to N-tert-butyl amides via the Ritter reaction was optimized employing tert-butyl acetate and acetic acid. The reaction has a broad scope for aromatic, alkyl, and α,β-unsaturated nitriles.
- Baum, Jean C.,Milne, Jacqueline E.,Murry, Jerry A.,Thiel, Oliver R.
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supporting information; experimental part
p. 2207 - 2209
(2009/07/01)
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- Synthesis and absolute configuration of (+)-pseudodeflectusin: Structural revision of aspergione B
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We report herein the total synthesis and determination of the absolute configuration of (+)-pseudodeflectusin. The total synthesis of (+)-pseudodeflectusin starting from o-anisic aid was achieved in 11 total steps with an overall yield of 2.0%. The 1
- Saito, Fumiyo,Kuramochi, Kouji,Nakazaki, Atsuo,Mizushina, Yoshiyuki,Sugawara, Fumio,Kobayashi, Susumu
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p. 4796 - 4799
(2007/10/03)
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- Synthesis and Biological Activity of the Putative Metabolites of the Atypical Antipsychotic Agent Tiospirone
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Putative oxidative metabolites of the lead antipsychotic agent tiospirone (1) were synthesized to assist in the identification of the authentic metabolic products found in human urine samples.Thus far, six authentic metabolites have been correlated to the synthetic species.The putative metabolites were further examined in vitro to assess their central nervous system therapeutic potential.SAR analysis of these derivatives indicates that hydroxyl substitution, particularly in the azaspirodecanedione region of the molecule, diminishes the dopamine D-2 affinity of the species without significantly altering the serotonin type-1A and type-2 interactions.In addition, an increase in α1-adrenergic affinity appears to be linked to the attenuation of effects at the dopamine receptors.The biological profile of the 6-hydroxytiospirone metabolite 42 was exemplary in these respects and the in vivo actions of this compound suggest potent antipsychotic potential with a minimal liability for extrapyramidal side effects (EPS).While compound 42 has been unambiguously characterized as an actual human metabolite of tiospirone, the role of 42 in the observed antipsychotic activity of the parent drug, if any, has not yet been determined.
- Cipollina, Joseph A.,Ruediger, Edward H.,New, James S.,Wire, Mary E.,Shepherd, Timothy A.,et al.
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p. 3316 - 3328
(2007/10/02)
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- ANALGESIC 1,2-BENZISOTHIAZOL-3-YLPIPERAZINE DERIVATIVES
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A series of non-opiate analgesics of Formula I STR1 wherein R 1 is hydrogen, alkyl, aralkyl, or aryloxyalkyl; R 2 is alkyl or hydrogen; and R 3 and R 4 are independently selected from hydrogen, alkyl, acyloxy, alkoxy, alkylthio, halogen, hydroxyl, or trifluoromethyl; or a pharmaceutically acceptable acid addition salt.
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- An Investigation into the Formation of Benzo- and Naphtho-pyrans by Cyclisation of ortho-Alkenyl(hydroxyalkyl)benzenes using either Cerium(IV) Ammonium Nitrate or Potassium t-Butoxide in Dimethylformamide
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A series of ortho-alkenylbenzyl alcohols carrying methoxy substituents at appropriate positions on the aromatic ring have been synthesised.Each of these compounds has been treated separately with each of the title reagents.
- Giles, Robin G. F.,Green, Ivan R.,Pestana, J. Alexandre X.
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p. 2389 - 2396
(2007/10/02)
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- Acylation of Amines and Alcohols by Anodic Oxidation of N-Phenyl-hydroxamic Acids
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The electrochemical acylation of amines and alcohols is described.The yield of products from the electrochemical reaction is markedly improved by the use of N-phenyl derivatives of hydroxamic acids in place of the N-hydrogen counterparts.Keywords - anodic oxidation; acylation of amine and alcohol; N-phenylhydroxamic acid; acetonitrile; glassy-carbon electrode
- Masui, Masaichiro,Ueshima, Takahiro,Yamazaki, Tomoko,Ozaki, Shigeko
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p. 2130 - 2133
(2007/10/02)
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