0000000000114025
AUTHOR
B. Abarca-gonzalez
Cycloaddition Reactions with Vinyl Heterocycles
Publisher Summary The Diels-Alder reaction is one of the most common and elegant methods for the construction of six-membered rings. Although the number of Diels-Alder cycloadditions with open-chain and alicyclic dienes is very large, the number of examples with aromatic heterocyclic compounds is relatively small. The introduction of a vinyl group as a substituent onto a heterocycle increases the number of possible reactions. This new possibility, however attractive for synthetic purposes, is successful only with π-excessive five-membered heterocyclic derivatives with a few exceptions. The chapter discusses the reactions of vinyl heterocycles with carbodienophiles. The endocyclic and exo-en…
ChemInform Abstract: Cycloaddition Reactions with Vinyl Heterocycles
Publisher Summary The Diels-Alder reaction is one of the most common and elegant methods for the construction of six-membered rings. Although the number of Diels-Alder cycloadditions with open-chain and alicyclic dienes is very large, the number of examples with aromatic heterocyclic compounds is relatively small. The introduction of a vinyl group as a substituent onto a heterocycle increases the number of possible reactions. This new possibility, however attractive for synthetic purposes, is successful only with π-excessive five-membered heterocyclic derivatives with a few exceptions. The chapter discusses the reactions of vinyl heterocycles with carbodienophiles. The endocyclic and exo-en…
Synthesis, Characterisation, and Reactivity of 1-(1-Methylimidazol-2-yl)ethenes
Abstract Thermally labile 1-(1-methylimidazol-2-yl)-ethenes, synthesised using the Wittig reaction, have been characterised as stable picrate or N-phenacyl salts. The free bases can be regenerated from the picrates on treatment with triethylamine and their reactivity with dienophiles is described.
The Chemistry of [1,2,3]Triazolo[1,5- a] pyridines
The reactivity of [1,2,3]triazolo[1,5-a]pyridines 1 is described. Triazolopyridines react with electrophiles in two contrasting ways, giving 3-substituted triazolopyridines 2, or products 3, resulting from triazolo ring opening with loss of molecular nitrogen. The triazolopyridines can be lithiated at -40 degrees C by lithium diisopropylamide in ether giving regiospecifically the 7-lithio derivative. Bromotriazolopyridines have activation towards nucleophilic substitution at position 5 and 7, and benzenoid inertness at position 6. The parent compound 1a is easily hydrogenated giving tetrahydrotriazolopyridine 11a in high yield; when the triazolopyridines have substituents, the hydrogenation…