the tert-amino effect in heterocyclic chemistry. synthesis of spiro heterocycles杂环化学的tert-amino效应。.pdfVIP

Molecules 2005, 10, 1101-1108 molecules ISSN 1420-3049 The tert-Amino Effect in Heterocyclic Chemistry. Synthesis of Spiro Heterocycles Elisaveta V. D’yachenko, Tatiana V. Glukhareva, Lyudmila V. Dyudya, Oleg V. Eltsov and Yury Yu. Morzherin* Department of Technology for Organic Synthesis (TOSLab), Urals State Technical University - UPI, 19, Mira str., Ekaterinburg, 620002, Russia. Tel. +7 (343)3754818, Fax: +7(343) 3754135 * Author to whom correspondence should be addressed; e-mail: morjerine@htf.ustu.ru Received: 23 April 2005 / Published: 30 September 2005 Abstract: The tert-amino reaction effect was examined. A new method to synthesize spiro heterocycles is presented. It was shown that the “tert-amino effect” could be applied to the formation of spiro-fused heterocycles. The formation of spiro compounds proceeds in most cases in good yields in a one-pot reaction. Keywords: Tert-amino effect, cyclization, spiro compounds, Knoevenagel condensation, 1,2,3-thiadiazole, pyrazole, quinoline The term tert-amino effect was coined by Meth-Cohn and Suschizky [1] to generalize cyclization reactions of certain ortho-substituted N,N-dialkylanilines. Ring closure of ortho-substituted N,N- dialkylaniline derivatives can proceed in three different ways, depending on the nature of A=B (Scheme 1). The first path (a) involves ring closure between the ortho substituted and the tert-nitrogen atom. The second path (b) comprises those reactions which involve one of the α-methylene groups attached to the atom A, ultimately leading to the formation of five membered rings. The thir