Microwave-assisted three-component coupling-addition-S(N)Ar (CASNAR) sequences to annelated 4H-thiopyran-4-ones.
A whole family of annelated 4H-thiopyran-4-ones as the core structural unit was readily synthesized in good yields by a microwave-assisted coupling-addition-S(N)Ar (CASNAR) sequence starting from readily available (het)aroyl chlorides, alkynes and sodium sulfide nonahydrate in a consecutive one-pot three-component reaction. All representatives display a pronounced halochromicity of the absorption bands upon protonation. According to DFT calculations, the electronic ground state of the annelated 4H-thiopyran-4-ones possess a considerable zwitterionic character.
Willy
Benjamin
B
Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr., 1, D-40225, Düsseldorf, Germany.
Frank
Walter
W
Müller
Thomas J J
TJ
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D004583:Electrons; D008872:Microwaves; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013053:Spectrophotometry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D011714:Pyrans; D013438:Sulfhydryl Compounds; C522033:thiopyran