- A facile synthesis of dibenzopyrroloazepinones as tetracyclic allocolchicinoids - An unusual 1,2-phenyl shift
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A facile synthesis of dibenzopyrroloazepinones via an electrophilic cyclisation of a biphenyl-acyliminium ion is described; an unusual 1,2-phenyl shift occurs when the C-1′ carbon is the more nucleophilic than the C-2′ carbon.
- Wu, Liang,Aliev, Abil E.,Caddick, Stephen,Fitzmaurice, Richard J.,Tocher, Derek A.,King, Frank D.
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- Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols
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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.
- 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
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p. 4149 - 4164
(2019/04/30)
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- Synthesis of 3-Hexyl-4-cyan-6,7-dimethoxy Isocoumarin
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4-(2-Amino-propanamideyl)-3,4,5,6,7,8,9,10-octahydro-5,6, 8-trihydroxy-3-methyl-isocoumarin, which was isolated from Flaveria bidentis (L) Kuntze, had herbicidal activity and its structure was modified in this research in order to get the isocoumarin comp
- Dong, Hai Jiao,Ban, Xu Dong,Li, Cheng,Huo, Jing Qian,Gong, Zhan Hu,Kang, Zhan Hai,Dong, Jin Gao,Zhang, Jin Lin
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p. 3623 - 3625
(2014/08/05)
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- Palladium-catalyzed tandem reaction to construct benzo[c]phenanthridine: Application to the total synthesis of benzo[c]phenanthridine alkaloids
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A concise and efficient synthesis of benzo[c]phenanthridines was accomplished by the palladium-catalyzed ring-opening coupling of azabicyclic alkene with o-iodobenzoates, followed by tandem cyclization. The strategy was successfully applied in the total synthesis of benzo[c]phenanthridine alkaloids such as sanguinarine, chelerythrine, nitidine and avicine.
- Lv, Pei,Huang, Kanglun,Xie, Longguan,Xu, Xiaohua
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p. 3133 - 3135
(2011/05/15)
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- Heck-mediated synthesis and photochemically induced cyclization of [2-(2-styrylphenyl)ethyl]carbamic acid ethyl esters and 2-styryl-benzoic acid methyl esters: Total synthesis of naphtho[2,1f]isoquinolines (2-azachrysenes)
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We describe two new closely related total syntheses of naphtho[2,1-f]isoquinolines. The first synthesis consists of a Heck coupling reaction between trifluoromethanesulfonic acid 2-(2-ethoxycarbonylaminoethyl)phenyl esters and styrenes to give [2-(2-styrylphenyl)ethyl]carbamic acid ethyl esters. These compounds cyclize to give (2-phenanthren-1-yl-ethyl)carbamic acid ethyl esters, from which 2-azachrysenes can be obtained in a three-step sequence. The second synthesis includes a new total synthesis of 2-styrylbenzoic acid methyl esters by Heck coupling of methyl o-iodobenzoates to styrenes, followed by the transformation of the resulting benzoic acid derivatives into phenanthrene-1-carboxylic acid methyl esters and then into the target compounds by a six-step sequence including a Bischler-Napieralski cyclization.
- Pampín, M. Carme,Estévez, Juan C.,Estévez, Ramón J.,Maestro, Miguel,Castedo, Luis
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p. 7231 - 7243
(2007/10/03)
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