109296-43-7Relevant academic research and scientific papers
α-nitro epoxides in organic synthesis: Development of a one-pot organocatalytic strategy for the synthesis of quinoxalines
Ibrahim, Mohammad M.,Grau, Dominik,Hampel, Frank,Tsogoeva, Svetlana B.
, p. 1401 - 1405 (2014/03/21)
A new strategy for the synthesis of biologically active quinoxalines by using versatile α-nitro epoxides as starting compounds has been developed. In addition, the in situ organocatalytic epoxidation of electron-poor nitro olefins followed by condensation with 1,2-phenylenediamines to provide quinoxalines in one pot has been demonstrated. The reaction of easily accessible nitro olefins with the tBuOOH/1,8-diazabicycloundec-7-ene (TBHP/DBU) organocatalytic system gives rise to the corresponding α-nitro epoxides, which are suitable for subsequent reaction with 1,2-phenylenediamines under mild conditions to give quinoxaline heterocycles in up to 82 % yield. Copyright
α-Nitro Epoxides in Organic Synthesis: Development of a One-Pot Organocatalytic Strategy for the Synthesis of Quinoxalines
Ibrahim, Mohammad M.,Grau, Dominik,Hampel, Frank,Tsogoeva, Svetlana B.
, p. 1401 - 1405 (2015/10/05)
A new strategy for the synthesis of biologically active quinoxalines by using versatile α-nitro epoxides as starting compounds has been developed. In addition, the in situ organocatalytic epoxidation of electron-poor nitro olefins followed by condensation with 1,2-phenylenediamines to provide quinoxalines in one pot has been demonstrated.
Nitroepoxides as versatile precursors to 1,4-diamino heterocycles
Vidal-Albalat, Andreu,Rodriguez, Santiago,Gonzalez, Florenci V.
supporting information, p. 1752 - 1755 (2014/04/17)
Nitroepoxides are easily transformed into 1,4-diamino heterocycles such as quinoxalines and pyrazines by treatment with 1,2-benzenediamines and ammonia, respectively. Additionally, related saturated heterocycles, such as piperazines and tetrahydroquinoxalines, can be accessed by treatment with 1,2-diamines and a reducing agent. These transformations are efficient, provide access privileged, bioactive structures, and produce minimal waste.
