64432-48-0Relevant academic research and scientific papers
Transition-metal-free decarboxylative thiolation of stable aliphatic carboxylates
Xing, Wei-Long,Liu, De-Guang,Fu, Ming-Chen
, p. 4593 - 4597 (2021/02/03)
A transition-metal-free decarboxylative thiolation protocol is reported in which primary, secondary, tertiary (hetero)aryl acetates and α-CN substituted acetates undergo the decarboxylative thiolation smoothly, to deliver a variety of functionalized aryl alkyl sulfides in moderate to excellent yields. Aryl diselenides are also amenable substrates for construction of C-Se bonds under the simple and mild reaction conditions. Moreover, the protocol is successfully applied to the late-stage modification of pharmaceutical carboxylates with satisfactory chemoselectivity and functional-group compatibility. This journal is
Synthesis of novel selenium and tellurium-containing tetrazoles: A class of chalcogen compounds with antifungal activity
Libero, Francieli M.,Xavier, Maurício C.D.,Victoria, Francine N.,Nascente, Patrícia S.,Savegnago, Lucielli,Perin, Gelson,Alves, Diego
scheme or table, p. 3091 - 3094 (2012/07/27)
We describe herein the synthesis and antifungal activity of new 5-arylchalcogenoalkyl-1H-tetrazoles 4. Arylchalcogenoalkyl-1H-tetrazoles 4 have been synthesized in high yields by reaction of arylchalcogenolate anions with chloronitriles 2, and subsequent
Formation of carbocycles by intramolecular conjugate displacement: Scopeand mechanistic insights
Wang, Lihong,Prabhudas, Bodhuri,Clive, Derrick L. J.
supporting information; experimental part, p. 6003 - 6012 (2009/09/25)
A detailed study has been made of a method of ring closure categorized as an all-carbon intramolecular conjugate displacement (ICD). This reaction involves intramolecular addition of a carbanion, which is stabilized by at least one electron-withdrawing group, to a Michael acceptor which has a leaving group in an allylic position. The process formally resembles a combination of Michael addition and S N2' displacement. The overall result is formation of a ring with loss of the allylic leaving group and shift of the original double bond to a new location spanning the positions of the electron-withdrawing substituent of the Michael acceptor subunit and the original allylic leaving group. The starting materials are easily prepared by a selenium-based version of the Morita-Baylis-Hillman reaction. The cyclizations are transition metal free and occur under mild conditions, using DBU or Cs 2CO 3 inMeCN or THF. Acetate is a suitable leaving group and the electron-withd rawing substituent of the Michael acceptor unit can be CO 2R,SO 2Ph, or CN. Six- and seven-membered rings are formed effi ciently, and complex structures, such as those resembling the core of CP-225,917, are easily assembled. The products of these ICD reactions are themselves classical Michael acceptors. A range of mechanisms probably operates, depending on the structure of the starting material and the reaction conditions, but conclusive evidence for a stepwise mechanism was obtained in a suitably biased case, while other observations are compatible with a concerted process or a stepwise path involving a short-lived carbanion that evades capture by a proton source.
Intramolecular conjugate displacement: A general route to hexahydroquinolizines, hexahydroindolizines, and related [m,n,0]-bicyclic structures with nitrogen at a bridgehead
Clive, Derrick L. J.,Li, Zhiyong,Yu, Maolin
, p. 5608 - 5617 (2008/02/09)
(Chemical Equation Presented) N-Protected amino aldehydes can be converted into allylic alcohols by the classical Morita-Baylis-Hillman reaction (cf. 2 → 3) or by condensation with selenium-stabilized carbanions, followed by oxidation (cf. 2 → 8 → 3). The
Fluorinations of α-seleno carboxylic acid derivatives with hypervalent (difluoroiodo)toluene
Arrica, Maria A.,Wirth, Thomas
, p. 395 - 403 (2007/10/03)
A very efficient synthesis of (difluoroiodo)toluene avoiding the use of elemental chlorine and elemental fluorine is described. We have fluorinated a series of α-acceptor substituted selenides using (difluoroiodo)toluene. The reactions are usually very clean and under the reaction conditions no further oxidized products are observed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
