One-pot multicomponent synthesis of azaindoles and pyrroles from one molecule of a silicon-tethered diyne and three or two molecules of organonitriles mediated by zirconocene.
A zirconocene-mediated one-pot multicomponent synthesis process leading to the synthesis of pyrrolo[3,2-c]pyridine (5-azaindoles) and pyrrole derivatives has been developed starting from a silicon-tethered diyne and three or two different or identical organonitriles. Pyrrolo[3,2-c]pyridine and pyrrole derivatives with diverse structures and substitution patterns have been highly selectively prepared by this protocol. A wide variety of organonitriles and silicon-tethered diynes, either aliphatic or aromatic with both electron-withdrawing and -donating groups, have been used to afford 5-azaindoles and/or pyrroles in good-to-excellent isolated yields. A key intermediate formed in the Cp(2)Zr(II)-mediated reaction of one (PhC[triple bond]C)(2)SiMe(2), two molecules of iPrCN and one p-tolylCN was characterised by X-ray single-crystal structural analysis, which has allowed us to gain a good understanding of the reaction process.
Zhang
Shaoguang
S
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
Sun
Xiaohua
X
Zhang
Wen-Xiong
WX
Xi
Zhenfeng
Z
D002384:Catalysis; D053280:Diynes / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*; D015040:Zirconium / Q000737:chemistry*
D053280:Diynes; D007211:Indoles; D009570:Nitriles; D009942:Organometallic Compounds; D011758:Pyrroles; C023398:Zirconocene dichloride; D015040:Zirconium; D012825:Silicon