10550-79-5Relevant academic research and scientific papers
A practical synthesis of (±)-α-isosparteine from a tetraoxobispidine core
Blakemore, Paul R.,Kilner, Colin,Norcross, Neil R.,Astles, Peter C.
, p. 4721 - 4724 (2005)
(Chemical Equation Presented) The title alkaloid was synthesized in racemic form from 3,7-diallyl-2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (7) by a regioselective diallylation reaction followed by double ring-closing olefin metathesis and exhaustive reduction. Tetraoxobispidine 7 was itself prepared in three simple operations from dimethyl malonate. The entire sequence to α-isosparteine was conducted on a multigram scale and proceeded without recourse to chromatography.
Highly stereoselective bimetallic complexes for lactide and ε-caprolactone polymerization
Pang, Xuan,Duan, Ranlong,Li, Xiang,Sun, Zhiqiang,Zhang, Han,Wang, Xianhong,Chen, Xuesi
, p. 57210 - 57217 (2015/01/09)
A series of Schiff-base compounds containing bimetallic ligands and two aluminum centers have been synthesized and characterized by 1H, 13C NMR and elemental analysis. These compounds could be successfully used as catalysts for the p
Synthesis and characterization of binuclear Co(II) complexes with bis(salen-type) ligands
R?is?nen, Minna T.,Korpi, Heikki,Sundberg, Markku R.,Savin, Alexander,Leskel?, Markku,Repo, Timo
, p. 203 - 209 (2013/02/23)
Two new, bridged bis(salen-type) ligand precursors, 1,1,3,3- tetrakis(salicylidene-3-iminopropyl)butylenediamine (I) and 1,1,3,3- tetra(salicylideneiminomethyl)propane (IV), were prepared by Schiff base condensation of salicylaldehyde with appropriate tet
Total synthesis of (±)-α-isosparteine, (±)-β- isosparteine, and (±)-sparteine from a common tetraoxobispidine intermediate
Norcross, Neil R.,Melbardis, John P.,Solera, Margarita Ferris,Sephton, Mark A.,Kilner, Colin,Zakharov, Lev N.,Astles, Peter C.,Warriner, Stuart L.,Blakemore, Paul R.
, p. 7939 - 7951 (2008/12/23)
(Chemical Equation Presented) The three title alkaloids were separately prepared in stereocontrolled fashion from a common tetraoxobispidine precursor, 3,7-diallyl-2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (16). Bisimide 16 was generated from malonate via acid promoted cyclization of the Knoevenagel condensation adduct 1,1,3,3-propanetetracarboxamide. (±)-α- Isosparteine (dl-2) was elaborated from 16 in 28% overall yield by a two-directional synthetic sequence composed of four reactions: double addition of allylmagnesium bromide, ring-closing olefin metathesis (RCM), hydrogenation, and borane mediated reduction. (±)-β-Isosparteine (dl-3) was targeted along similar lines by a strategic reversal in allylation and reduction operations on the core synthon. Thus, 16 was advanced to dl-3 in five steps and 12% overall yield by a reaction sequence commencing with sodium borohydride mediated reduction and followed by double Sakurai-type allylation of the resulting bishemiaminal. The synthesis of dl-3 was concluded by RCM and then global reduction (H2, Pd/C; LiAlH4). The final target, (±)-sparteine (dl-1), was secured in six steps and 11% overall yield from 16 by monoreduction and Sakurai allylation, followed by allyl Grignard addition and then RCM and global reduction as before. Reasons for the inherent C 2-type regioselectivity of net double nucleophilic additions to tetraoxobispidines are discussed and enantioselective oxazaborolidine mediated reduction of the N,N′-dibenzyl congener of 16 is reported.
Synthesis, Physicochemical and Pharmacological Properties of N,N′,N″, N?-Substituted Amides of 1,1,3,3- Propanetetracarboxylic Acid
Bezuglyi,Georgiyants,Perekhoda,Garnaya,Sych
, p. 475 - 477 (2007/10/03)
By condensation of symmetrical malonic acid diamides with dichloromethane (method a) and with paraform (method b) N,N′,N″,N?- substituted amides of 1,1,3,3-propanetetracarboxylic acid were synthesized. Better yields of the target products (68-80%) and the use of less toxic reagents indicate that method b is more feasible. The primary pharmacological screening revealed that the compounds obtained possess pronounced anticonvulsant activity at moderate toxicity.
