Heterocycles

Heterocycles - Heterocyclic Chemistry Professor J. Stephen...

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1 Heterocyclic Chemistry Heterocyclic Chemistry Professor J. Stephen Clark Room C4-04 Email: stephenc@chem.gla.ac.uk http://www.chem.gla.ac.uk/staff/stephenc/UndergraduateTeaching.html 2010 2011
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2 Recommended Reading Heterocyclic Chemistry – J. A. Joule, K. Mills and G. F. Smith Heterocyclic Chemistry (Oxford Primer Series) – T. Gilchrist Aromatic Heterocyclic Chemistry – D. T. Davies
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3 Course Summary • Definition of terms and classification of heterocycles • Functional group chemistry: imines, enamines, acetals, enols, and sulfur-containing groups • Synthesis of pyridines Introduction Intermediates used for the construction of aromatic heterocycles Synthesis of aromatic heterocycles Examples of commonly used strategies for heterocycle synthesis Carbon–heteroatom bond formation and choice of oxidation state Pyridines • General properties, electronic structure • Electrophilic substitution of pyridines • Nucleophilic substitution of pyridines • Metallation of pyridines Pyridine derivatives • Structure and reactivity of oxy-pyridines, alkyl pyridines, pyridinium salts, and pyridine N -oxides Quinolines and isoquinolines • General properties and reactivity compared to pyridine • Electrophilic and nucleophilic substitution quinolines and isoquinolines • General methods used for the synthesis of quinolines and isoquinolines
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4 Course Summary (cont) • General properties, structure and reactivity of pyrroles, furans and thiophenes • Methods and strategies for the synthesis of five-membered heteroaromatics • Fisher and Bischler indole syntheses Five-membered aromatic heterocycles Electrophilic substitution reactions of pyrroles, furans and thiophenes Metallation of five-membered heteroaromatics and use the of directing groups Strategies for accomplishing regiocontrol during electrophilic substitution Indoles • Comparison of electronic structure and reactivity of indoles to that of pyrroles • Reactions of indoles with electrophiles • Mannich reaction of indoles to give 3-substituted indoles (gramines) • Modification of Mannich products to give various 3-substituted indoles 1,2 and 1,3-Azoles • Structure and reactivity of 1,2- and 1,3-azoles • Synthesis and reactions of imidazoles, oxazoles and thiazoles • Synthesis and reactions of pyrazoles, isoxazoles and isothiazoles
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5 Introduction • Heterocycles contain one or more heteroatoms in a ring • Aromatic, or partially or fully saturated – this course will focus on aromatic systems • Heterocycles are important and a large proportion of natural products contain them X Y X Y X Z carbocycle heterocycles - X , Y , Z are usually O , N or S • Many pharmaceuticals and agrochemicals contain at least one heterocyclic unit • Heterocyclic systems are important building-blocks for new materials possessing interesting electronic, mechanical or biological properties
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6 Classification – Aromatic Six-Membered Isoelectronic carbocycle
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Heterocycles - Heterocyclic Chemistry Professor J. Stephen...

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