title: Synthesis of pyrido[2,3-e]pyrrolo[1,2-a]pyrazine derivatives via tandem iminium cyclization and smiles rearrangement.
abstract: 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.
authors: The Center for Combinatorial Chemistry and Drug Discovery, Jilin University, 75 Haiwai St., Changchun, Jilin 130012, PR China.
authors: Jinbao
authors: J
authors: Xiang
authors: Hongxiang
authors: H
authors: Xie
authors: Dongsheng
authors: D
authors: Wen
authors: Qun
authors: Q
authors: Dang
authors: Xu
authors: X
authors: Bai
mesh_terms: 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
chemical_list: D000447:Aldehydes; D007097:Imines; D011719:Pyrazines; D011758:Pyrroles; C529355:pyrido(2,3-e)pyrrolo(1,2-a)pyrazine