Inverse electron-demand Diels-Alder reactions of 1,2,4-triazines, where the dienophile is present in a sidechain tethered to the azadiene, can proceed with remarkable facility, leading to a variety of condensed pyridines (Scheme 1). Several recent publications from our laboratory have served to illu
Intramolecular Diels-Alder reactions of 1,2,4-triazines: Synthesis of tricyclic condensed pyridines and pyrazines
β Scribed by Edward C. Taylor; Larry G. French
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 187 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Syntheses of several 6,6,6-tricyclic condensed pyridines and pyrazines utilizing intramolecular Diels-Alder reactions of 1,2,4-triazines with alkyne and nitrile dienophiles are detailed. The cyclizations are facilitated by the presence 01 conformationally restrictive planar aromatic rings in the chain tethering the diene and the dienophile.
π SIMILAR VOLUMES
Imidazole and 2-phenylimidazoleundergo intramolecularcycloadditions with 1,2,4triazines tethered betweenan imidazolenitrogenand the triazinylC3 position with a trimethylene chainto producetetrahydro-l,5-naphthyridines followingloss of N2 and a nitrile.
Alkylation of 1,2,4-triazine-6-thiones with 4-iodobutyne, followed by oxidation to the sulfoxide and intramolecular cycloaddition (at room temperature), gives 2,3-dihydrothieno[2,3-c]pyridines, which are readily dehydrated with acetic anhydride to thieno[2,3\_c]pyridines. The same series of reactio
3-(3-Butynyloxy)-and 3-(4-pentnyfoxy)-1,2,4-triazines undergo facile intramolecular Diels-Alder reactions to yield 2,3-dihydrofuro(2,3-@pyridines and dihydropyrano(2,3-&)pyridines respectively. The former are readily dehydrogenated with DDQ to furo(2,3\_l$pyridines.