a new pathway to 3-hetaryl-2-oxo-2h-chromenes on the proposed mechanisms for the reaction of 3-carbamoyl-2-iminochromenes with dinucleophiles新途径3-hetaryl-2-oxo-2h-chromenes拟议的机制与dinucleophiles 3-carbamoyl-2-iminochromenes的反应.pdfVIP

Molecules 2000, 5, 1146–1165 molecules ISSN 1420-3049 A New Pathway to 3-Hetaryl-2-oxo-2H-chromenes: On the Proposed Mechanisms for the Reaction of 3-Carbamoyl-2- iminochromenes with Dinucleophiles Sergiy M. Kovalenko,* Igor E. Bylov, Konstantyn M. Sytnik, Valentyn P. Chernykh and Yaroslav V. Bilokin Department of Organic Chemistry, Ukrainian National Academy of Pharmacy, Kharkiv 61002, Ukraine. * Author to whom correspondence should be addressed; E-mail: kovalenko_sergey@ukrfa.kharkov.ua Received: 30 July 2000 / Accepted: 19 September 2000 / Published: 31 October 2000 Abstract : The present account summarizes the authors studies to elucidate the mechanisms of the recently reported rearrangements resulting from inter- and/or intramolecular reactions of 2-imino-2H-chromene-3-carboxamides with different dinucleophiles. Keywords: rearrangements, mechanisms, iminochromenes, nucleophiles. Introduction The coumarin (2H-chromen-2-one) moiety is often found in natural products [1]. In view of the ubiquity of this fragment in a variety of biologically active compounds, the synthesis of various 2H- chromen-2-one analogs is important in gauging their potential as a source of chemotherapeutics [2]. As part of our investigations on the reactivity of 3-carbamoyl-2-imino-2H-chromenes [3], we recently introduced a new method for synthesis of 3-hetaryl-2-oxo-2H-chromenes [4]. This method was based on the rearrangements of 2-imino-2H-chromene-3-carboxamides into 3-hetaryl-2-oxo-2H-chromenes under the action of dinucleophiles. In this account, results of our studies on clarification of the mechanism of the