Cyano Diels−Alder and Cyano Ene Reactions. Applications in a Formal [2 + 2 + 2] Cycloaddition Strategy for the Synthesis of Pyridines

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

J. Am. Chem. Soc., 2010, 132 (38), pp 13203–13205

DOI: 10.1021/ja106901u

Publication Date (Web): September 3, 2010

Abstract

Two metal-free, formal [2 + 2 + 2] cycloaddition strategies for the construction of polycyclic pyridine derivatives are described that proceed via pericyclic cascade mechanisms featuring the participation of unactivated cyano groups as enophile and dienophile cycloaddition partners.

Experimental procedures, characterization data, and ¹H and ¹³C NMR spectra for all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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Cyano Diels−Alder and Cyano Ene Reactions. Applications in a Formal [2 + 2 + 2] Cycloaddition Strategy for the Synthesis of Pyridines

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Cyano Diels−Alder and Cyano Ene Reactions. Applications in a Formal [2 + 2 + 2] Cycloaddition Strategy for the Synthesis of Pyridines

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