title: Skeletally Diverse Synthesis of Innovative [2,1-c]-1,4-Oxazepine and [1,4]-Quinoxaline Systems.
abstract: An efficient, innovative synthesis of [2,1-c]-1, 4-oxazepine and [1,4]-quinoxaline heterocycles along with the embodied pyrimido-pyrrolo motifs was established. Initially, the pyrrole ring was installed using microwave irradiation through an intramolecular base-catalyzed cyclization between acetyl bromomethyl pyrimidine dione and o-amino phenyl methanol or o-phenylenediamine methyl benzoates. Furthermore, oxazepine, and quinoxaline scaffolds were constructed by an acid-catalyzed condensation with a variety of aldehydes by an unconventional Pictet-Spengler reaction strategy. An important aspect of this work is to build novel heterocyclic ring systems with potential medicinal interest.
authors.affiliation: Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.|Department of Medicinal and Applied Chemistry, Kaohsiung Medical University , 100, Shih-Chuan First Road, Kaohsiung 807-08, Taiwan.
authors.forename: Chia-Hsin
authors.initials: CH
authors.lastname: Lee
authors.affiliation: Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.
authors.forename: Wen-Chun
authors.initials: WC
authors.lastname: Wu
authors.affiliation: Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.
authors.forename: Prasad S
authors.initials: PS
authors.lastname: Dangate
authors.affiliation: Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.
authors.forename: Li-Ching
authors.initials: LC
authors.lastname: Shen
authors.affiliation: Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.
authors.forename: Wen-Sheng
authors.initials: WS
authors.lastname: Chung
authors.affiliation: Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan.|Department of Medicinal and Applied Chemistry, Kaohsiung Medical University , 100, Shih-Chuan First Road, Kaohsiung 807-08, Taiwan.
authors.forename: Chung-Ming
authors.initials: CM
authors.lastname: Sun
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D007202:Indicators and Reagents; D008872:Microwaves; D008958:Models, Molecular; D008968:Molecular Conformation; D010077:Oxazepines / Q000138:chemical synthesis*; D011810:Quinoxalines / Q000138:chemical synthesis*
chemical_list: D000447:Aldehydes; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D010077:Oxazepines; D011810:Quinoxalines
keywords: oxazepine; pyrimido-pyrrolo motifs; quinoxaline; unconventional Pictet−Spengler reaction strategy