title: Copper-catalyzed intramolecular cyclization of N-propargyl-adenine: synthesis of purine-fused tricyclics.
abstract: A novel protocol to construct fluorescent purine-fused tricyclic products via intramolecular cyclization of N-propargyl-adenine has been developed. With CuBr as the catalyst, a series of purine-fused tricyclic products were obtained in good to excellent yields (19 examples, 75-89% yields). When R2 was a hydrogen atom in N-propargyl-adenines, the reactions only afforded the endocyclic double bond products. When R2 was an aryl group, the electron-donating groups favored the endocyclic double bond products, while the electron-withdrawing groups favored the exocyclic double bond products.
authors.affiliation: Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University , Xinxiang, Henan 453007, PR China.
authors.forename: Ren-Long
authors.initials: RL
authors.lastname: Li
authors.forename: Lei
authors.initials: L
authors.lastname: Liang
authors.forename: Ming-Sheng
authors.initials: MS
authors.lastname: Xie
authors.forename: Gui-Rong
authors.initials: GR
authors.lastname: Qu
authors.forename: Hong-Ying
authors.initials: HY
authors.lastname: Niu
authors.forename: Hai-Ming
authors.initials: HM
authors.lastname: Guo
mesh_terms: D000225:Adenine / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009019:Morphinans / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009019:Morphinans; C440369:N-propargyl; D011083:Polycyclic Compounds; D011687:Purines; D003300:Copper; D000225:Adenine; C030985:purine