29170-03-4Relevant academic research and scientific papers
Metal-Free Insertion Reactions of Diazo Carbonyls to Azlactones
De Mello, Amanda C.,Momo, Patrícia B.,Burtoloso, Antonio C. B.,Amarante, Giovanni W.
, p. 11399 - 11406 (2018/09/12)
Insertion reactions of diazo carbonyls to azlactones in basic conditions have been performed. The developed method allows the preparation of a wide range of oxazole derivatives in yields ranging from 74 to 98%. Different substituents on both azlactone rings and diazo carbonyls do not compromise the methodology, even those containing stereogenic centers. Isotopic labeling experiments revealed the mechanism may proceed through a rare diazo carbonyl activation by an ammonium salt derivative.
One-step syntheses of substituted 2-pyrrolidinones and 3-pyrrolidinones from α,β-unsaturated diazoketones and amines. Application in the synthesis of barmumycin
Dias, Rafael M.P.,Momo, Patrícia B.,Burtoloso, Antonio C.B.
, p. 3720 - 3729 (2017/06/13)
A simple and one-pot way to prepare substituted 2- and 3-pyrrolidinones is described. The method uses unsaturated diazoketones (obtained from aldeydes in a single step) and amines, and provide an easy access to these important classes of nitrogen heterocycles. Furthermore, application of this methodology to the synthesis of the natural product barmumycin is achieved in 3 steps from these diazoketones.
One-pot synthesis of polyfunctional pyrazoles: An easy access to α-diazoketones from arylglyoxal monohydrates and tosylhydrazine
Shu, Wen-Ming,Ma, Jun-Rui,Zheng, Kai-Lu,Sun, Hui-Ying,Wang, Mei,Yang, Yan,Wu, An-Xin
, p. 9321 - 9329 (2015/03/05)
A new and efficient method for the generation of α-diazoketones has been developed from arylglyoxal monohydrates and tosylhydrazine at room temperature. 1,3-Dipolar cycloaddition reactions were used to constructing polyfunctional pyrazole derivatives by the reaction of generated α-diazoketones in situ with electron-deficient alkenes, quinones and coumarins in one pot. The one-dimensional molecular packing of 1H-benzo[f]indazole-4,9-dione derivatives along the c direction demonstrated a helical chain formation via N-H?O hydrogen-bonding.
A two-step synthesis of the bioprotective agent JP4-039 from N-Boc-l-leucinal
Bernardim, Barbara,Burtoloso, Antonio C.B.
, p. 3291 - 3296 (2014/05/06)
An expedited synthesis of the bioprotective agent JP4-039 is described from N-Boc-l-leucinal in 50% overall yield. The synthesis involves the use of an α,unsaturated diazoketone as the key intermediate, followed by a photochemical Wolff rearrangement in t
Preparation of Z-α,β-unsaturated diazoketones from aldehydes. Application in the construction of substituted dihydropyridin-3-ones
Rosset, Isac G.,Burtoloso, Antonio C. B.
, p. 9464 - 9470 (2013/10/08)
The stereoselective preparation of α,β-unsaturated diazoketones with Z geometry is described from aldehydes and a new olefination reagent. When prepared from amino aldehydes, these diazoketones could be converted to substituted dihydropyridin-3-ones in just one step, after an intramolecular N-H insertion reaction. The straightforward synthesis of a natural trihydroxylated piperidine demonstrates the utility of these unsaturated diazoketones for the rapid construction of piperidines.
Preparation of α,β-unsaturated diazoketones employing a Horner-Wadsworth-Emmons reagent
Pinho, Vagner D.,Burtoloso, Antonio C. B.
supporting information; experimental part, p. 289 - 292 (2011/03/19)
A new method for the preparation of α,β-unsaturated diazoketones from aldehydes and a Horner-Wadsworth-Emmons reagent is reported. The method was applied to the short synthesis of two substituted pyrrolidines.
Aziridinyl vinyl ketones from the asymmetric catalytic aziridination reaction
Deng, Yonghong,Young, Rok Lee,Newman, Cory A.,Wulff, William D.
, p. 2068 - 2071 (2008/02/04)
Under the aegis of boron Lewis acids, prepared from either the vanol or vapol ligand, vinyl aziridinyl ketones can be obtained with a high degree of asymmetric induction from the catalytic asymmetric aziridination reaction (AZ) of imines and vinyl diazome
