Synthesis of pyrido[2,3-e]pyrrolo[1,2-a]pyrazine derivatives via tandem iminium cyclization and smiles rearrangement.
The tandem iminium cyclization and Smiles rearrangement of pyridinyloxyacetaldehyde 1 and a primary amine generated a novel pyrido[2,3-e]pyrrolo[1,2-a]pyrazine scaffold. TFA was discovered to be an efficient catalyst in the reactions with aromatic amines, whereas TiCl4 was found to be superior in the case of aliphatic amines. This methodology proved to be efficient in the preparation of a library of diversified pyrido[2,3-e]pyrrolo[1,2-a]pyrazine derivatives.
Xiang
Jinbao
J
The Center for Combinatorial Chemistry and Drug Discovery, Jilin University, 75 Haiwai St., Changchun, Jilin 130012, PR China.
Xie
Hongxiang
H
Wen
Dongsheng
D
Dang
Qun
Q
Bai
Xu
X
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D007097:Imines; D011719:Pyrazines; D011758:Pyrroles; C529355:pyrido(2,3-e)pyrrolo(1,2-a)pyrazine