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Synthesis of highly substituted benzene ring systems through three-component coupling of enyne imines,Fischer carbene complexes,and electron-deficient alkynes
Authors:Bishnu Dhakal  Lalith SR Gamage  Yanshi Zhang  James W Herndon
Institution:Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003, USA
Abstract:Three-component coupling of Fischer carbene complexes, enyne aldehyde hydrazones, and electron-deficient alkynes leads to simple benzoate derivatives in a process involving the formation of an N-aminopyrrole derivative, Diels-Alder reaction, and nitrene extrusion. The products are readily converted into isoquinolones through reaction with primary amines. The reaction proceeds best with highly substituted and electron-rich pyrroles even though these are the sterically least favorable substrates, and this reactivity trend is supported by a computational study.
Keywords:Fischer carbene complexes  Benzannulation  Benzene ring synthesis  Pyrroles  Diels-Alder reaction  Isoquinolones  Conjugated alkynes  Hydrazones  Nitrene extrusion  HOQSUCISQQPHLF-PTGBLXJZSA-N  ISORBTXDCPJJPN-UHFFFAOYSA-N  IKFDIAIJVHFJSG-UHFFFAOYSA-N  QATLHAMOOQQKBO-UHFFFAOYSA-N  CSCHBVQSIZGZFW-UHFFFAOYSA-N  PKWALMYERLARMO-ZHACJKMWSA-N  GJZUDALIWQGBKA-UHFFFAOYSA-N  QQIMQVZKXTYDFI-UHFFFAOYSA-N  QKDJIFMNUBINOX-UHFFFAOYSA-N  DNOOFSBCCJJUMC-UHFFFAOYSA-N  FHXZWWNJJACEGQ-UHFFFAOYSA-N  WAGFAJBWOMGVFE-UHFFFAOYSA-N
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