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
Further intramolecular reactions of 1,2,4-triazines. Synthesis of furo[2,3-b]pyridines and dihydropyrano[2,3-b]pyridines
โ Scribed by Edward C. Taylor; John E. Macor
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 168 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
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.
๐ SIMILAR VOLUMES
In a three-step sequence starting from readily available starting materials, 2,3-carbon disubstituted furo[2,3-b]pyridines can be accessed in good yields and purity. Furo[2,3-b]pyridines bearing ester, amide and ketone groups at the 2-position can be prepared with a variety of aryl and alkyl groups
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
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