Synthesis of highly substituted benzene ring systems through three-component coupling of enyne imines,Fischer carbene complexes,and electron-deficient alkynes |
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Authors: | Bishnu Dhakal Lalith SR Gamage Yanshi Zhang James W Herndon |
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Institution: | Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003, USA |
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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. |
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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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