Development of Synthetic Methodologies for Heterocycles Using Diene-transmissive Hetero-Diels-Alder Reaction

The diene-transmissive hetero-Diels-Alder reaction (DTHDA reaction) is a special case of the DTDA reaction in which one or more heteroatoms are contained within either a cross-conjugated triene/polyene (heterodendralene) pi-system, a dienophile pi-system or both. Therefore, the DTHDA protocol is an efficient and attractive method for the stereoselective synthesis of a variety of heterocyclic systems. Merits and potential of the DTHDA methodology for heterocyclic synthesis can be widely extended by structural variations and complexity of both diene and dienophile; the kind, numbers, and positions of heteroatoms contained in either the cross-conjugated triene/polyene ( [3/n] heterodendralene) or the dienophile framework, as well as the inter or intramolecular cycloaddition mode, and its predictable regio- and stereoselectivities. In this paper, we introduce the synthesis of a variety of heterocycles using the DTHDA reaction with a focus on our research.