16188-57-1Relevant articles and documents
A mild and simple regioselective iodination of activated aromatics with iodine and catalytic ceric ammonium nitrate
Das, Biswanath,Krishnaiah, Maddeboina,Venkateswarlu, Katta,Reddy, V. Saidi
, p. 81 - 83 (2007)
Molecular iodine in the presence of a catalytic amount of CAN has been utilized efficiently for regioselective iodination of activated aromatic compounds under mild reaction conditions.
Synthesis of 8-azaprotosappanin A derivatives via intramolecular palladium-catalyzed ortho C-H activation/C-C cyclization and their antibacterial activity
Zhou, Xuan,Fu, Wanyong,Jiang, Hongshuo,Wang, Chenglong,Ju, Chao,Chu, Wenyi,Sun, Zhizhong
, p. 1956 - 1960 (2017)
A novel synthetic protocol for the construction of eight-membered heterocycles by intramolecular palladium-catalyzed ortho C-H activation/C-C cyclization was proposed. With protosappanin A as the lead compound, 25 derivatives of 8-azaprotosappanin A were prepared in good yields by this protocol. Besides, a plausible reaction mechanism of the intramolecular cyclization was proposed. This strategy could be widely used in the synthesis of some natural products and drugs with large heterocycles due to the fast reaction rate and the mild conditions. In vitro antimicrobial activities of the synthesized compounds were assessed against the strains of Gram-positive bacteria and linezolid and ciprofloxacin were selected as the standard drugs. Some of the synthesized compounds were found to have excellent antibacterial activities.
Synthesis of 1,4-benzoxazepine derivatives via a novel domino aziridine ring-opening and isocyanide-insertion reaction
Ji, Fei,Lv, Mei-Fang,Yi, Wen-Bin,Cai, Chun
, p. 3401 - 3406 (2013)
A novel and efficient domino process has been developed for the synthesis of 1,4-benzoxazepine derivatives from a range of readily accessible N-tosylaziridines, 2-iodophenols and isocyanides. This process involves the aziridine ring-opening reaction with 2-iodophenol, followed by a palladium-catalyzed isocyanide-insertion reaction. This regioselective and high-yielding transformation could be extended to its application for the synthesis of natural products and biologically interesting heterocycles. Copyright
Synthesis and antimicrobial activity of δ-viniferin analogues and isosteres
Catinella, Giorgia,Dallavalle, Sabrina,Krogfelt, Karen Angeliki,Mattio, Luce Micaela,Musso, Loana,Pedersen, Kasandra Juliet,Pinna, Cecilia,Pinto, Andrea
supporting information, (2021/12/24)
The natural stilbenoid dehydro-δ-viniferin, containing a benzofuran core, has been recently identified as a promising antimicrobial agent. To define the structural elements relevant to its activity, we modified the styryl moiety, appended at C5 of the ben
Palladium-Catalyzed Chemoselective Oxidative Addition of Allyloxy-Tethered Aryl Iodides: Synthesis of Medium-Sized Rings and Mechanistic Studies
Liu, Ce,Li, Yuke,Shi, Wei-Yu,Ding, Ya-Nan,Zheng, Nian,Liu, Hong-Chao,Liang, Yong-Min
supporting information, p. 4311 - 4316 (2021/05/26)
This Letter describes a Pd-catalyzed Tsuji-Trost-type/Heck reaction with allyloxy-tethered aryl iodides and aziridines. The strategy provides efficient access to benzannulated medium-sized rings via intermolecular cyclization. The substrate aryl iodide ha
Biomimetic carbene cascades enabled imine derivative migration from carbene -bearing thiocarbamates
Li, Xue,Chen, Haohua,Xuan, Qingqing,Mai, Shaoyu,Lan, Yu,Song, Qiuling
supporting information, p. 3518 - 3523 (2021/05/29)
Inspired by the body circulation of Omeprazole (irreversible proton pump inhibitor), we disclose the carbene-triggered cascades for the synthesis of 2-aminobenzofuran derivatives from N-sulfonyl-1,2,3-triazoles or benzothioazole-bearing thiocarbamates, which represents an unprecedented imine derivative migration process. Furthermore, the desulfurizing reagent-free Barton-Kellogg-type reactions starting from N-sulfonyl-1,2,3-triazoles have also been achieved for the first time, and elemental sulfur is confirmed as a byproduct during this transformation. Both experimental data and DFT calculations further thoroughly explained the unique reactivity.
Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols
Satkar, Yuvraj,Yera-Ledesma, Luisa F.,Mali, Narendra,Patil, Dipak,Segura-Quezada, Luis A.,Ramírez-Morales, Perla I.,Solorio-Alvarado, César R.,Navarro-Santos, Pedro
, p. 4149 - 4164 (2019/04/30)
An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chemistry calculations revealed PhII(OH)·NH3 to be the most plausible iodinating active species as a reactive "I+" synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit.
Oxyacylation of Iodoalkynes: Gold(I)-Catalyzed Expeditious Access to Benzofurans
Fernández-Canelas, Paula,Rubio, Eduardo,González, José M.
supporting information, p. 6566 - 6569 (2019/08/20)
(Acetonitrile)[1,3-bis(2,6-diisopropylphenyl)-imidazole-2-ylidene] gold(I) catalyzes the cycloisomerization of 2-(iodoethynyl)aryl esters to give 3-iodo-2-acyl benzofurans. This catalytic transformation is the result of an unprecedented selective syntheti
One-pot ortho-amination of aryl C-H bonds using consecutive iron and copper catalysis
Henry, Martyn C.,McGrory, Rochelle,Faggyas, Réka J.,Mostafa, Mohamed A. B.,Sutherland, Andrew
, p. 4629 - 4639 (2019/05/17)
A one-pot approach for ortho-coupling of arenes with non-actived N-nucleophiles has been developed using sequential iron and copper catalysis. Regioselective ortho-activation of anisoles, anilines and phenols was achieved through iron(iii) triflimide catalysed iodination, followed by a copper(i)-catalysed, ligand-assisted coupling reaction with N-heterocycle, amide and sulfonamide-based nucleophiles. The synthetic utility of this one-pot, two-step method for the direct amination of ortho-aryl C-H bonds was demonstrated with the late-stage functionalisation of 3,4-dihydroquinolin-2-ones. This allowed the preparation of a TRIM24 bromodomain inhibitor and a series of novel analogues.
A Convenient Palladium-Catalyzed Carbonylative Synthesis of (E)-3-Benzylidenechroman-4-ones
Wang, Wei-Feng,Peng, Jin-Bao,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
supporting information, p. 3521 - 3524 (2019/02/14)
A convenient palladium-catalyzed carbonylation reaction for the efficient synthesis of (E)-3-benzylidenechroman-4-ones has been developed. Using TFBen as a solid CO source, a range of substituted (E)-3-benzylidenechroman-4-ones were prepared in moderate to good yields with 2-iodophenols and allyl chlorides as the substrates. Additionally, substituted quinolin-4(1H)-ones can also be obtained with 2-iodoaniline as the starting material.
