Heterocyclic Chemistry at a Glance
Pyrroles 85 Exercises Two isomeric mono-nitro-derivatives, C 5 H 6 N 2 O 2 , are formed in a ratio of 6:1, by treating 2-methyl ...
Heterocyclic Chemistry at a Glance, Second Edition. John A. Joule and Keith Mills. © 2013 John Wiley & Sons, Ltd. Published ...
Indoles 87 a Friedel–Crafts catalyst: 3-acetylation simply requires heating with acetic anhydride; trifl uoroacetylation proceed ...
88 Indoles Vilsmeier reactions in an intramolecular sense, at an indole -position, generate 3,4-dihydro--carbolines. Even indo ...
Indoles 89 -Alkylation of 3-alkyl-substituted indoles by cationic reagents involves a rearrangement of a fi rst-formed 3,3-dial ...
90 Indoles C-Metallated indoles N-Substituted indoles can be C-deprotonated, with very strong bases, selectively at the -positi ...
Indoles 91 3-Lithio-indoles are usually generated via metal-halogen exchange processes, however direct 3-lithiation of indoles w ...
92 Indoles Oxidation and reduction Indoles are easily autoxidised in the reactive heterocyclic ring. Conversion of 3-substituted ...
Indoles 93 Reactivity of side-chain substituents The electron-rich character of indoles gives rise to some special properties of ...
94 Indoles Oxygen substituents Indoles with a hydroxyl group on the benzene ring behave as normal phenols. ‘2-Hydroxyindole’ exi ...
Indoles 95 Alternative routes to arylhydrazines for Fischer cyclisations are useful, for example aryl halides can be substrates ...
96 Indoles Synthesis of indoles from ortho-aminoaryl alkynes (1,2-bond made) With the advent of palladium-catalysed cross-coupli ...
Indoles 97 Synthesis of isatins from anilines (1,2- and 3,3a-bonds made) Isatins can be readily prepared via the reaction of an ...
98 Indoles Like indole, they undergo electrophilic substitution in the fi ve-membered ring but have the advantage of not being a ...
Heterocyclic Chemistry at a Glance, Second Edition. John A. Joule and Keith Mills. © 2013 John Wiley & Sons, Ltd. Published ...
100 Furans and Thiophenes Vilsmeier formylation and Friedel–Crafts acylations proceed effi ciently with thiophene and furan, usi ...
Furans and Thiophenes 101 C-Metallated thiophenes and furans In thiophene and furan chemistry, there is, of course, no equivalen ...
102 Furans and Thiophenes Palladium(0)-catalysed reactions Boron and tin derivatives are known at - and -positions of furan an ...
Furans and Thiophenes 103 Peracids convert thiophenes into S,S-dioxides that are no longer aromatic (no electrons on the sulfur ...
104 Furans and Thiophenes There are many examples of intramolecular furan cycloadditions and of the construction of complex poly ...
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