6652-42-2Relevant academic research and scientific papers
Controlled Synthesis of 1,3,5-Oxadiazin-2-ones and Oxazolones through Regioselective Iodocyclization of Ynamides
Huang, Hai,Zhu, Xiaolin,He, Guangke,Liu, Qi,Fan, Junzhen,Zhu, Hongjun
, p. 2510 - 2513 (2015)
Two efficient processes based on the iodocyclization of ynamides have been developed: (i) N-alkynyl tert-butyloxycarbamates were found to undergo a rare 6-exo-dig ring closure reaction affording 1,3,5-oxadiazin-2-ones by using acetonitrile as solvent; (ii) In the absence of acetonitrile, N-alkynyl tert-butyloxycarbamates could undergo 5-endo-dig cyclization providing oxazolones. (Chemical Equation Presented).
Palladium-catalyzed intramolecular cyclization of ynamides: Synthesis of 4-halo-oxazolones
Huang, Hai,He, Guangke,Zhu, Guohao,Zhu, Xiaolin,Qiu, Shineng,Zhu, Hongjun
, p. 3480 - 3487 (2015/04/14)
A mild and efficient methodology involving Pd(PPh3)4-catalyzed intramolecular cyclization of N-alkynyl alkyloxycarbamates with CuCl2 or CuBr2 for the synthesis of 4-halo-oxazolones was developed. This reaction exhibiting good functional tolerance provided a new, efficient, and rapid synthetic process to 4-halo-oxazolones. The resulting 4-halo-oxazolones can serve as great potential precursors for the 3,4,5-trisubstituted oxazolones via a Pd-catalyzed cross-coupling reaction.
Preparation of 3,4,5-trisubstituted oxazolones by pd-catalyzed coupling of n -alkynyl tert -butyloxycarbamates with aryl halides and related electrophiles
Lu, Zenghui,Cui, Weijian,Xia, Siyuan,Bai, Yihui,Luo, Fang,Zhu, Gangguo
, p. 9871 - 9877,7 (2012/12/12)
A novel palladium-catalyzed approach for the assembly of 3,4,5-trisubstituted oxazolones has been achieved by the coupling of N-alkynyl tert-butyloxycarbamates with aryl halides and related electrophiles, which involves an oxidative addition followed by oxypalladation/reductive elimination. The reaction provides a convenient access to diversely substituted oxazolones in satisfactory yields and shows good functional group compatibility.
A single-step synthesis of 4-oxazolin-2-ones and their use in the construction of polycyclic structures bearing quaternary stereocenters
Santoyo, Blanca M.,Gonzalez-Romero, Carlos,Merino, Omar,Martinez-Palou, Rafael,Fuentes-Benites, Aydee,Jimenez-Vazquez, Hugo A.,Delgado, Francisco,Tamariz, Joaquin
experimental part, p. 2505 - 2518 (2009/09/25)
A new method for the synthesis of 4-oxazolin-2-ones by a one-pot MW-promoted condensation of a-ketols and isocyanates is reported. An alternative thermal approach using the same starting materials is also described. These cyclic enamides were efficient nucleophiles, reacting with Michael acceptors and prenyl bromide to give a variety of polycyclic structures bearing one or two quaternary stereocenters. The selectivity of the products depended on the reaction conditions and on the electrophile used. Wiley-VCH Verlag GmbH & Co. KGaA.
Cyclization Reaction of Bis(tributylstannylated) α-Ketols with Heterocumulenes. Preparation of O,O-Vinylene Imino- and Thiocarbonates
Sakai, Shizuyoshi,Murata, Masashi,Wada, Nobuto,Fujinami, Tatsuo
, p. 1873 - 1874 (2007/10/02)
Aromatic α-ketols reacted with diethylaminotributylstannane at 60 deg C to afford a mixture of (Z)- and (E)-1,2-bis(tributylstannyloxy)-1,2-diarylethenes, which were allowed to react with organic isothiocyanates and carbon disulfide to give substituted O,
Substitution and Addition Reactions at Spiro-Oxiranes
Siegel, Hannes,Wittmann, Helga
, p. 1005 - 1018 (2007/10/02)
Nucleophilic substitution at the spiro carbon atom as well as the CH2-group takes place with spiro-oxiranes 1, 6 and 7, whose spiro carbon atom bear electron withdrawing substituents.In some cases by elimination of formaldehyde a transformation to the cor
