Tandem vicarious nucleophilic substitution of hydrogen/intramolecular Diels-Alder reaction of 1,2,4-triazines into functionalized cycloalkenopyridines.

نویسندگان

  • Danuta Branowska
  • Stanisław Ostrowski
  • Andrzej Rykowski
چکیده

Synthesis of 2,3- and 3,4-cyclopentenopyridines, 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydroisoquinolines from 1,2,4-triazine derivatives is reported. Introduction of an alpha-functionalized methyl substituent (e.g. arylsulphonyl, sulphonamide, sulphonic acid ester) into position 3- or 6- of triazines by vicarious nucleophilic substitution of hydrogen and subsequent alkylation with alkyl iodides bearing an acetylenic function in terminal position afforded valuable intermediates for intramolecular Diels-Alder reaction with inverse electron demand. When heated at higher temperature, these triazine derivatives gave the Diels-Alder cycloadducts, which, after spontaneous extrusion of nitrogen moiety, led to a variety of functionalized cycloalkenopyridine derivatives.

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عنوان ژورنال:
  • Chemical & pharmaceutical bulletin

دوره 50 4  شماره 

صفحات  -

تاریخ انتشار 2002