127958-19-4Relevant articles and documents
Method for site-selective alkylation of Diazine-N-oxide using phosphonium ylides
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Paragraph 0176; 0177; 0259; 0260; 0264; 0265, (2021/04/06)
- N - Oxide (Diazine -)N-The position selective Oxides-C alkylation of H) relates to a method alkylation. To the present invention, a plurality of diazine compounds can be alkylated by selectively introducing an alkyl group to a diazine compound known as a core unit structure in a medicine, and synthesis of a plurality of diazine compounds (varenicline) paenibacillin A, which is a natural product, can be synthesized.
Site-Selective C-H Alkylation of Diazine N-Oxides Enabled by Phosphonium Ylides
Ghosh, Prithwish,Kwon, Na Yeon,Han, Sangil,Kim, Saegun,Han, Sang Hoon,Mishra, Neeraj Kumar,Jung, Young Hoon,Chung, Sang J.,Kim, In Su
supporting information, p. 6488 - 6493 (2019/08/20)
The synthesis of alkylated diazine derivatives is important for their practical utilization as pharmaceuticals and for other purposes. Herein, we describe the metal-free site-selective C-H alkylation of diazine N-oxides using phosphonium ylides that affords a variety of alkylated diazine derivatives with broad functional group tolerance. The utility of this method is showcased by the late-stage functionalization of a commercially available drug such as varenicline. Notably, the sequential C-H alkylation of pyrazine N-oxides for the total synthesis of a pyrazine-containing natural product, paenibacillin A, highlights the importance of this method.
Enforced helicity: Efficient access to self-organized helical molecular strands by the imine route
Gardinier, Kevin M.,Khoury, Richard G.,Lehn, Jean-Marie
, p. 4124 - 4131 (2007/10/03)
The condensation of the two oligoheterocyclic aldehydes 8 and 16 with the bis-hydrazine 17 gives the bis-hydrazones 1 and 2. These molecular strands are shown to adopt helical conformations of 1.5 and 2.5 turns, respectively. The helical shape of 1 has be
Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles. VIII. Synthesis of Ethyl and Methyl 2,4-Disubstituted 5-Pyrimidinecarboxylates
Schenone, Pietro,Sansebastiano, Laura,Mosti, Luisa
, p. 295 - 305 (2007/10/02)
Reaction of ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates with N-C-N dinucleophiles such as guanidine, acetamidine or benzamidine afforded in high yields the relative esters of 4-substituted 2-amino-, 2-methyl- or 2-phenyl-5-pyrimidinecarboxylic acids, respectively.These esters were hydrolyzed to the corresponding carboxylic acids, which were converted by heating to 4-substituted 2-pyrimidinamines, 2-methyl or 2-phenylpyrimidines, respectively, generally in excellent yields.The 4-unsubstituted ethyl 2-amino-, 2-methyl- and 2-phenyl-5-pyrimidinecarboxylateswere obtained in moderate yields by reaction of the above dinucleophiles with ethyl 2,2-diformylacetate.These esters were hydrolyzed and the corresponding acids (with the exception of the 2-methyl derivative) were decarboxylated to give 2-pyrimidinamine and 2-phenylpyrimidine in satisfactory yields.
