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
Diels-Alder reactions of 1,2,4-triazines. Synthesis of thieno[2,3-c]pyridines and 3,4-dihydro-2H-thiopyrano[2,3-c]pyridines from 6-(alkynylthio)-1,2,4-triazines
β Scribed by Taylor, Edward C.; Macor, John E.
- Book ID
- 121199711
- Publisher
- American Chemical Society
- Year
- 1989
- Tongue
- English
- Weight
- 809 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
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
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.