The first synthesis of thieno[c]isoquinolines and an improved synthesis of phenanthridine and thieno[c]quinolines through pd(0) catalyzed coupling of ortho-formylarylboronic acids with functionalized aryl halides |
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Authors: | Youhua Yang Anna-Britta Hrnfeldt Salo Gronowitz |
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Institution: | Youhua Yang,Anna-Britta Hörnfeldt,Salo Gronowitz |
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Abstract: | All three isomeric hitherto unknown thienoc]isoquinolines have been synthesized in high yields by the Pd(0)-catalyzed coupling of 2-formylbenzeneboronic acid with t-butyl-N-(ortho-halothienyl)carbaniates. When 2-bromoacetanilide, instead of 2-bromoaniline, was coupled with orth-formylarylboronic acids under Pd-catalysis, phenanthridine and thienoc]quinolines were obtained in improved yields. Total assignments of 1H nmr spectra of thienoc]isoquinolines and thienoc]quinolines are reported. Assignments are based on high resolution 300 MHz 1H nmr spectra, two-dimentional 1H-13C chemical shift correlation spectra and one-dimentional INADEQUATE 13C nmr spectroscopy. |
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