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    Heterocyclic compound:

    A heterocyclic compound is a cyclic

    compound which has atoms of at least two

    different elements as members of its

    ring(s).[1] The counterparts of heterocyclic

    compounds are homocyclic compounds,

    the rings of which are made of a single

    element.

    http://en.wikipedia.org/wiki/Cyclic_compoundhttp://en.wikipedia.org/wiki/Cyclic_compoundhttp://en.wikipedia.org/wiki/Chemical_elementhttp://en.wikipedia.org/wiki/Heterocyclic_compoundhttp://en.wikipedia.org/wiki/Homocyclic_compoundhttp://en.wikipedia.org/wiki/Homocyclic_compoundhttp://en.wikipedia.org/wiki/Heterocyclic_compoundhttp://en.wikipedia.org/wiki/Heterocyclic_compoundhttp://en.wikipedia.org/wiki/Heterocyclic_compoundhttp://en.wikipedia.org/wiki/Chemical_elementhttp://en.wikipedia.org/wiki/Cyclic_compoundhttp://en.wikipedia.org/wiki/Cyclic_compound

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    , a heterocyclic compoundPyridine

    http://en.wikipedia.org/wiki/Pyridinehttp://en.wikipedia.org/wiki/Pyridinehttp://en.wikipedia.org/wiki/File:Pyridine.svg

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    cyclo-octasulfur, a homocyclic compound

    http://en.wikipedia.org/wiki/Allotropes_of_sulfurhttp://en.wikipedia.org/wiki/Allotropes_of_sulfurhttp://en.wikipedia.org/wiki/File:Cyclooctasulfur_structural_formula_3D.svghttp://en.wikipedia.org/wiki/Allotropes_of_sulfurhttp://en.wikipedia.org/wiki/Allotropes_of_sulfurhttp://en.wikipedia.org/wiki/Allotropes_of_sulfurhttp://en.wikipedia.org/wiki/Allotropes_of_sulfurhttp://en.wikipedia.org/wiki/Allotropes_of_sulfurhttp://en.wikipedia.org/wiki/Allotropes_of_sulfurhttp://en.wikipedia.org/wiki/Allotropes_of_sulfurhttp://en.wikipedia.org/wiki/Allotropes_of_sulfurhttp://en.wikipedia.org/wiki/Allotropes_of_sulfur

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    Although heterocyclic compounds may beinorganic, most contain at least one carbonatom, and one or more atoms of elements

    other than carbon within the ring structure,such as sulfur, oxygen ornitrogen.[2] Since inorganic chemistry non-carbons usually areconsidered to replace carbon atoms, they are

    called heteroatoms, meaning 'different fromcarbon and hydrogen' (rings of heteroatomsof the same element are homocyclic).

    http://en.wikipedia.org/wiki/Compoundhttp://en.wikipedia.org/wiki/Inorganic_compoundhttp://en.wikipedia.org/wiki/Carbonhttp://en.wikipedia.org/wiki/Sulfurhttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Nitrogenhttp://en.wikipedia.org/wiki/Heterocyclic_compoundhttp://en.wikipedia.org/wiki/Organic_chemistryhttp://en.wikipedia.org/wiki/Heteroatomhttp://en.wikipedia.org/wiki/Heteroatomhttp://en.wikipedia.org/wiki/Organic_chemistryhttp://en.wikipedia.org/wiki/Heterocyclic_compoundhttp://en.wikipedia.org/wiki/Heterocyclic_compoundhttp://en.wikipedia.org/wiki/Heterocyclic_compoundhttp://en.wikipedia.org/wiki/Nitrogenhttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Sulfurhttp://en.wikipedia.org/wiki/Carbonhttp://en.wikipedia.org/wiki/Inorganic_compoundhttp://en.wikipedia.org/wiki/Compound

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    Heterocyclic chemistry is the branch of

    chemistry dealing with synthesis,

    properties, and applications of

    heterocycles.

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    Heterocyclic compounds in

    selected areas of life:

    in general: nucleic acids, amino acids(proteins), Chlorophyll

    feeding: proteins, carbohydrates, vitamins

    alkaloids: nicotine, caffeine

    antibiotics (penicillins, sulfonamides)

    psychopharmacologic agents

    (benzodiazepines) insecticides (triazoles)

    herbicides (triazines, pyridines)

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    Properties:

    cyclic systems with carbon and hetero-atoms

    (N, O, S)

    heteroaliphatic compounds:

    similar properties like aliphatic compounds

    heteroaromatic compounds: similar properties like aromatic compounds

    Size of the cyclic system:

    5-7 atoms: stable, easy to synthesise

    > 7 atoms: stable, hardly to synthesise < 5 atoms: unstable, more or less easy

    to synthesise

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    HeterocyclesAcceptable prefixes include:

    O=Oxa

    S=Thia

    N=Aza

    When there is more than one hetero-atom,

    preference is given to O, then S, then N, thenC. Mnemonic: Old Soldiers Never Cry.

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    Suffix:

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    Suffixes for fully

    saturated compounds

    Suffixes for fully

    unsaturated compound

    Ring size

    Without N

    With N

    Without NWith N

    -iraneiridine-ireneIrine3

    -etaneetidine-ete-ete4

    -olaneolidine-ole-ole5

    -inane-in-ine6

    -epane-epin-epine7

    -ocaneocin-ocine8

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    Oxygen Containing Heterocycles

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    Heterocycles Containing

    Nitrogen

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    Five-membered Rings Containing

    Nitrogen and Another Heteroatom

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    Heterocycles Containing Sulfur

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    6 Membered Rings Containing One

    Nitrogen

    Piperidine Pyridine

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    6 Membered Rings Containing Two

    Nitrogens

    Piperazine

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    7 Membered Rings

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    More Complex Unsaturated Ring

    Systems

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    More Complex Unsaturated Ring

    Systems

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    Examples in Drugs

    Naphazoline Captopril

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    Diazepam Cyprohepatidine

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    Nizatidine Phenytoin

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    Ciprofloxacine

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    Classification based on

    electronic structure: Heterocyclic compounds can be usefully

    classified based on their electronic

    structure. The saturated heterocycles

    behave like the acyclic derivatives. Thus,piperidine and tetrahydrofuran are

    conventional amines and ethers, with

    modified steric profiles. The study ofheterocyclic chemistry therefore focuses

    especially on unsaturated derivatives.

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    , and the preponderance of work and

    applications involves unstrained 5- and 6-

    membered rings. Included are pyridine,

    thiophene, pyrrole, and furan. Anotherlarge class of heterocycles are fused to

    benzene rings, which for pyridine,

    thiophene, pyrrole, and furan arequinoline, benzothiophene, indole, and

    benzofuran, respectively.

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    Fusion of two benzene rings gives rise to a

    third large family of compounds,

    respectively the acridine,

    dibenzothiophene, carbazole, anddibenzofuran. The unsaturated rings can

    be classified according to the participation

    of the heteroatom in the pi-system

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    3-Membered rings:

    Heterocycles with three atoms in the ring

    are more reactive because of ring strain.

    Those containing one heteroatom are, in

    general, stable. Those with twoheteroatoms are more likely to occur as

    reactive intermediates.

    Common 3-membered heterocycles withone heteroatom are:

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    UnsaturatedSaturatedHeteroatom

    AzirineAziridineNitrogen

    OxireneOxirane (ethylene oxide,

    epoxides)

    Oxygen

    ThiireneThiirane (episulfides)Sulfur

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    Those with two heteroatoms include:

    UnsaturatedSaturatedHeteroatom

    DiazirineNitrogen

    OxaziridineNitrogen/oxygen

    DioxiraneOxygen

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    4-Membered rings:

    Compounds with one heteroatom:

    UnsaturatedSaturatedHeteroatom

    AzeteAzetidineNitrogen

    OxeteOxetaneOxygen

    ThieteThietaneSulfur

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    Compounds with two heteroatoms:

    HeteroatomSaturatedUnsaturated

    NitrogenDiazetidine

    OxygenDioxetaneDioxete

    SulfurDithietaneDithiete

    http://en.wikipedia.org/w/index.php?title=Diazetidine&action=edit&redlink=1http://en.wikipedia.org/wiki/Dioxetanehttp://en.wikipedia.org/w/index.php?title=Dioxete&action=edit&redlink=1http://en.wikipedia.org/wiki/Dithietanehttp://en.wikipedia.org/wiki/Dithietehttp://en.wikipedia.org/wiki/Dithietehttp://en.wikipedia.org/wiki/Dithietanehttp://en.wikipedia.org/w/index.php?title=Dioxete&action=edit&redlink=1http://en.wikipedia.org/wiki/Dioxetanehttp://en.wikipedia.org/w/index.php?title=Diazetidine&action=edit&redlink=1

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    5-Membered rings:

    With heterocycles containing five atoms,

    the unsaturated compounds are frequently

    more stable because ofaromaticity.

    Five-membered rings with one

    heteroatom:

    http://en.wikipedia.org/wiki/Unsaturated_compoundhttp://en.wikipedia.org/wiki/Aromaticityhttp://en.wikipedia.org/wiki/Aromaticityhttp://en.wikipedia.org/wiki/Unsaturated_compound

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    HeteroatomSaturatedUnsaturated

    Nitrogen(Azolidine isPyrrolidine

    not used)

    (Azole is notPyrrole

    used)

    Oxygen(OxolaneTetrahydrofuran

    is rare)

    (Oxole is notFuran

    used)

    SulfurThiolane(Thiole is notThiophene

    used)

    BoronBorolaneBorole

    PhosphorusPhospholanePhosphole

    ArsenicArsolaneArsoleAntimonyStibolaneStibole

    BismuthBismolaneBismole

    SiliconSilolaneSilole

    TinStannolaneStannole

    http://en.wikipedia.org/wiki/Nitrogenhttp://en.wikipedia.org/wiki/Pyrrolidinehttp://en.wikipedia.org/wiki/Pyrrolehttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/Furanhttp://en.wikipedia.org/wiki/Sulfurhttp://en.wikipedia.org/wiki/Thiolanehttp://en.wikipedia.org/wiki/Thiophenehttp://en.wikipedia.org/wiki/Boronhttp://en.wikipedia.org/wiki/Borolehttp://en.wikipedia.org/wiki/Phosphorushttp://en.wikipedia.org/wiki/Phospholehttp://en.wikipedia.org/wiki/Arsenichttp://en.wikipedia.org/wiki/Arsolehttp://en.wikipedia.org/wiki/Antimonyhttp://en.wikipedia.org/wiki/Stibolehttp://en.wikipedia.org/wiki/Bismuthhttp://en.wikipedia.org/wiki/Bismolehttp://en.wikipedia.org/wiki/Siliconhttp://en.wikipedia.org/wiki/Silolehttp://en.wikipedia.org/wiki/Tinhttp://en.wikipedia.org/wiki/Stannolehttp://en.wikipedia.org/wiki/Stannolehttp://en.wikipedia.org/wiki/Tinhttp://en.wikipedia.org/wiki/Silolehttp://en.wikipedia.org/wiki/Siliconhttp://en.wikipedia.org/wiki/Bismolehttp://en.wikipedia.org/wiki/Bismuthhttp://en.wikipedia.org/wiki/Stibolehttp://en.wikipedia.org/wiki/Antimonyhttp://en.wikipedia.org/wiki/Arsolehttp://en.wikipedia.org/wiki/Arsenichttp://en.wikipedia.org/wiki/Phospholehttp://en.wikipedia.org/wiki/Phosphorushttp://en.wikipedia.org/wiki/Borolehttp://en.wikipedia.org/wiki/Boronhttp://en.wikipedia.org/wiki/Thiophenehttp://en.wikipedia.org/wiki/Thiolanehttp://en.wikipedia.org/wiki/Sulfurhttp://en.wikipedia.org/wiki/Furanhttp://en.wikipedia.org/wiki/Tetrahydrofuranhttp://en.wikipedia.org/wiki/Oxygenhttp://en.wikipedia.org/wiki/Pyrrolehttp://en.wikipedia.org/wiki/Pyrrolidinehttp://en.wikipedia.org/wiki/Nitrogen

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    The 5-membered ring compounds

    containing two heteroatoms, at least one

    of which is nitrogen, are collectively called

    the azoles. Thiazoles and isothiazolescontain a sulfur and a nitrogen atom in the

    ring. Dithiolanes have two sulfur atoms.

    http://en.wikipedia.org/wiki/Azolehttp://en.wikipedia.org/wiki/Thiazolehttp://en.wikipedia.org/wiki/Isothiazolehttp://en.wikipedia.org/wiki/Dithiolanehttp://en.wikipedia.org/wiki/Dithiolanehttp://en.wikipedia.org/wiki/Isothiazolehttp://en.wikipedia.org/wiki/Thiazolehttp://en.wikipedia.org/wiki/Azole

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    HeteroatomSaturatedUnsaturated (and

    partially unsaturated)

    Nitrogen/nitrogenImidazolidine

    Pyrazolidine

    )Imidazoline(Imidazole

    )Pyrazoline(Pyrazole

    Nitrogen/oxygenOxazolidineIsoxazolidine

    )Oxazoline(OxazoleIsoxazole

    Nitrogen/sulfurThiazolidine

    Isothiazolidine

    )Thiazoline(Thiazole

    Isothiazole

    Oxygen/oxygenDioxolane

    Sulfur/sulfurDithiolane

    http://en.wikipedia.org/wiki/Imidazolidinehttp://en.wikipedia.org/wiki/Pyrazolidinehttp://en.wikipedia.org/wiki/Imidazolinehttp://en.wikipedia.org/wiki/Imidazolehttp://en.wikipedia.org/wiki/Pyrazolinehttp://en.wikipedia.org/wiki/Pyrazolehttp://en.wikipedia.org/wiki/Oxazolidinehttp://en.wikipedia.org/wiki/Isoxazolidinehttp://en.wikipedia.org/wiki/Oxazolinehttp://en.wikipedia.org/wiki/Oxazolehttp://en.wikipedia.org/wiki/Isoxazolehttp://en.wikipedia.org/wiki/Thiazolidinehttp://en.wikipedia.org/w/index.php?title=Isothiazolidine&action=edit&redlink=1http://en.wikipedia.org/wiki/Thiazolinehttp://en.wikipedia.org/wiki/Thiazolehttp://en.wikipedia.org/wiki/Isothiazolehttp://en.wikipedia.org/wiki/Dioxolanehttp://en.wikipedia.org/wiki/Dithiolanehttp://en.wikipedia.org/wiki/Dithiolanehttp://en.wikipedia.org/wiki/Dioxolanehttp://en.wikipedia.org/wiki/Isothiazolehttp://en.wikipedia.org/wiki/Thiazolehttp://en.wikipedia.org/wiki/Thiazolinehttp://en.wikipedia.org/w/index.php?title=Isothiazolidine&action=edit&redlink=1http://en.wikipedia.org/wiki/Thiazolidinehttp://en.wikipedia.org/wiki/Isoxazolehttp://en.wikipedia.org/wiki/Oxazolehttp://en.wikipedia.org/wiki/Oxazolinehttp://en.wikipedia.org/wiki/Isoxazolidinehttp://en.wikipedia.org/wiki/Oxazolidinehttp://en.wikipedia.org/wiki/Pyrazolehttp://en.wikipedia.org/wiki/Pyrazolinehttp://en.wikipedia.org/wiki/Imidazolehttp://en.wikipedia.org/wiki/Imidazolinehttp://en.wikipedia.org/wiki/Pyrazolidinehttp://en.wikipedia.org/wiki/Imidazolidine

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    A large group of 5-membered ring

    compounds with three heteroatoms also

    exists. One example is dithiazoles that

    contain two sulfur and a nitrogen atom


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