[reaction: see text] In contrast to the Diels-Alder reaction of fulvenes and various alkenes, 6-aminofulvenes react with maleic anhydride (or maleimide) to give [6 + 2] cycloaddition adducts, constituting an efficient and novel route to pentaleno[1,2-c]furan, pentaleno[1,2-c]pyrrole, and cyclopenta[a]pentalene skeleton.
[reaction: see text] Regioselective and stereoselective inverse-electron-demand Diels-Alder reaction of N-sulfonyl-1-aza-1,3-butadiene with fulvenes are described. The methodology provides an efficient and novel route to tetrahydro-[1]pyrindine systems.
Fused pyridine derivatives R 0450Azadiene Diels-Alder Cycloaddition of Fulvenes: A Facile Approach to the [1]Pyrindine System. -The regioselective and stereoselective hetero [4 + 2] cycloadditions emphasize a new feature of the reactivity of fulvene and azadienes. The methodology represents an unprecedented approach to the title system. -(HONG*, B.-C.; WU, J.-L.; GUPTA, A. K.; HALLUR, M. S.; LIAO, J.-H.; Org. Lett. 6 (2004) 20, 3453-3456; Dep. Chem. Biochem., Natl. Chung Cheng Univ., Chia-Yi 621, Taiwan; Eng.) -Steudel 04-160
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