ORGANIC CHEMISTRY III HETEROCYCLIC COMPOUNDS BY: DR. MUNTHER A.M.ALI
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1 ORGAIC CHEMISTRY III HETEROCYCLIC COMPOUDS BY: DR. MUTHER A.M.ALI
2 A CYCLIC ORGAIC COMPOUDS Carbocyclic compounds, made up by carbon atoms. Heterocyclic compounds, at least one other atom which usually, O or S. Heterocyclic compounds (H.Cs.) can be classified into: Saturated, unsaturated and aromatic compounds. Saturated cyclic analogues of amine, ethers, thioethers, amides,..etc. Aromatic cyclic behave similar to benzene (aromaticity). H.Cs. ring may contain more than one hetero atom. H.Cs. occur widely in nature and non-naturally occurring compounds. For examples: alkaloids, antibiotics, essential amino acids, the vitamins, hemoglobin, the hormones, and large number of synthetic drugs.
3 THE GEERAL STRUCTURE: Where, X, Y and Z are usually, O or S. If X, Y and Z are C, the compounds called Carbocyclic compounds (C.Cs.)
4 CLASSIFICATIO OF H.CS. Cyclic organic compounds Heterocyclic Compounds (H.Cs.) Carbocyclic Compounds (C.Cs.) onaromatic containing unsaturated bonds onaromatic (Aliphatic, saturated) Aromatic and Unsaturated Fused-ring Monocyclic Fused-ring Monocyclic Monocyclic containing more than one hetero atom Monocyclic containing one hetero atom Monocyclic containing more than one hetero atom Monocyclic containing one hetero atom 3 membered ring 3 membered ring 3 membered ring 3 membered ring 4 membered ring 5 membered ring 6 membered ring 7 membered ring 8 membered ring 4 membered ring 5 membered ring 6 membered ring 7 membered ring 8 membered ring 4 membered ring 5 membered ring 6 membered ring 7 membered ring 8 membered ring 4 membered ring 5 membered ring 6 membered ring 7 membered ring 8 membered ring
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15 OMECLATURE There are two types, Special name or called Trivial name, as pyrrole, thiophine, furan. Systematic name or IUPAC. According to this system, monocyclic 3-8 membered rings are named by combining prefix in Table 1 with a suffix in Table 2, and a from end of prefix has been omitted. Table 1 O=Oxa =Aza S=Thia Table 2 Ring size Unsaturated compounds Saturated compounds With Without With Without 3 -irine -irene -iridine -irane 4 -ete -ete -etidine -etane 5 -ole -ole -olidine -olane 6 -ine -in -ane -ane 7 -epine -epin -epane -epane 8 -ocine -ocine -ocin -ocane
16 EXAMPLES Azirine Oxetane Thiole Azane
17 DERIVATIVES OF MOOCYCLIC COMPOUDS COTAIIG OE HETEROATOM IS: The number of heteroatom is always 1, the substituted group is in the sequence 2-Methylazete 2,4-Dimethylthietane 3-Ethyl-4-methyloxin
18 HETEROCYCLIC COMPOUDS COTAIIG MORE THA OE HETEROATOM: Two or more similar atoms are indicated by prefixes di-, tri-, etc. placed before the name and after the number of position. H H 1,4-Dithiin H 1,2,4-Triazolidine Two or more different hetero atoms named by combing the prefixes in Table 1 with suffix in Table 2 in order of O, S and. H O Oxaziridine O H 1,4-Oxazine
19 Partially saturated H.Cs. Partly saturated rings are denoted by the suffixes according to Table 2, and the prefixes dihydro-, tetrahydro-, etc. should be used. The numbering is started from the heterocyclic atom toward the saturated carbon atom. O O H O 2,3-Dihydro-oxole 1,2-Dihydro-azete 2,3-Dihydro-[1,4]dioxine
20 Indicated hydrogen In some cases, heterocyclic systems occur as one or more structural isomers which differ only in the position of an H-atom. These isomers are designated by indicating the number corresponding to the position of the hydrogen atom in front of the name, followed by an italic capital H. Such a prominent H- atom is called an indicated hydrogen and must be assigned the lowest possible location. H CH 3 O 2H-Oxete 2,3-Dihydro-1H-pyrrole 4-Methyl-2,3-dihydro-azete 2,3-Dihydro-1H-azole
21 Bicyclic systems with one benzene ring and one heteroatom Systems in which at least two neighboring atoms are common to two or more rings are known as fused systems. For several bicyclic benzo-fused heterocycles, trivial names are permitted, e.g.: Use the prefix benzo- and the trivial name of the heterocyclic component as follows: H Indole Benzo[b]pyrrole O Benzo[b]furan O Benzo[c]furan
22 The letters a, b, c indicated to site of heteroatom a b c a X b c Give the name of the following: S
23 Substituted Bicyclic systems The numbering of atom in bicyclic system is the following direction: X Br 3-Bromo-2-ethyl-6-methyl-quinoline O 2 O 2 S F H S Cl
24 Aromaticity of heterocyclic compounds Aromatic compounds are very stable due to resonance stability of the conjugated electrons and overlapping bonds. Look for the following 4 criteria to identify aromatic compounds
25 Cyclic, Cycle or cyclic implies a ring Planar, Since aromaticity relies on the ability of orbitals to overlap, the ring must have its atoms in the same plane. The molecule must be flat. sp2 carbons are trigonal planar or simply flat
26 Conjugated, You may have memorized that conjugated systems have alternating single and double bonds. sp2 atoms capable of resonance Huckel s Rule Huckel s Rule: 4n+2 = umber of Resonating Electrons
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28 Pyridine: An Aromatic Six-Membered Heterocyclic Compound The structure of pyridine considerably resembles that of benzene. It may be formally derived from the structure of benzene through the exchange of one ring carbon for a nitrogen. However, is pyridine, which is structurally and electronically allied to benzene, also aromatic?.
29 The nitrogen of pyridine is sp2-hybridized and possesses one lone electron pair. This electron pair is located in an sp2 orbital that is parallel to the ring plane. The nitrogen's lone electron pair of pyridine does not participate in the aromatic π electron system. Huckel s Rule: 4n+2 = umber of Resonating Electrons = 6 n = 1 aromatic Similar for all six membered ring containing more than one atom
30 Aromatic Five-Membered Heterocyclic Compound Pyrrole furan thiophene H O S
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34 TRIVIAL AME OF SOME H.CS.
35 AZOLE AD AZIE The H.Cs. containing one or more nitrogen atoms may have various structures with 5 and 6 membered aromatic monocyclic ring, as shown: Azole H H 1,2-Diazole 1,2,3-Triazole H 1,3-Diazole 1,2,4-Triazole H H 1,2,3,4-Tetrazole H
36 Azine 1,2-Diazine 1,3-Diazine 1,4-Diazine 1,2,3-Triazine 1,2,4-Triazine 1,3,5-Triazine 1,2,3,4-Tetrazine 1,2,4,5-Tetrazine
37 MEDICIAL USES OF HETEROCYCLIC COMPOUDS: (1) Antibiotics comes from Greek anti (against) and bios (life), are drugs can destroy bacteria or prevent their reproduction. -Lactam antibiotics H Which containing the azetidine group (A) Penicillin analogous Penicillin G Penicillin V Another examples, afcillin, Cloxacillin, Amoxicillin
38 (B) Cephalosporin Drug R1 R2 Cefradine -CH 3 H 2 Ceftrizoxime -H Ceftriaxone
39 (C) Other -Lactam Ertapenem Clavulanic acid Augmentin drug (amoxicillin and clavulanic acid)
40 (2) Macrolide antibiotic Large drugs containing macrocyclic lactone ring (macrolide ring). The lactone rings are usually 14, 15 and 16membered. H 3 C H 3 C CH 3 OH OH H 3 C H 3 C O H 3 C OH CH 3 HO O O CH 3 CH 3 CH 3 O O O CH 3 CH 3 O CH 3 OH CH 3 Erythromycin Azithromycin
41 (3) Quinolone antibiotics alidixic acid is first generation of quinolone used in 1962 for treatment of urinary tract infections (UTI) in human CH 3 H 3 C O O OH alidixic acid Ciprofloxacin Moxifloxacin
42 (4) Sulfonamide antibiotics Containing p-aminobenzoic sulfonamide, called sulfa drugs, for examples for these types of drugs: ame of drug R ame of heterocyclic ring Sulfadiazine Pyrimidine Sulfamethazine Methazine Sulfamethoxazole Methoxazole
43 (2) Antiviral Drugs Treatment viral infections, for example, Ritonavir is antiretroviral drug used to treat HIV (Human Immunodeficiency virus) and AIDS (Acquired Immunodeficiency Syndrome). Ritonavir Another example: elfinavir
44 (3) Antifungal Drugs Treatment fungal infections. The azole antifungal include two brood classes, Triazoles and Imidazoles Triazole drugs Fluconazole Voriconazole Ravuconazole
45 Imidazole Drugs Antihelminthics or Anthelmintics drugs (anti-parasitic) expel parasitic worms (helminthes) from body. Tinidazole Mebendazole
46 (4) Anticonvulsants Drugs (antiepileptic) Treatment epileptic seizures. Phenobarbital (diazane ring) Oxcarbaepine (azepine ring) Troxidone (oxazolidine ring) Phensuximide (succinimide ring)
47 (5) Antipyretic and on steroidal anti inflammatory Drugs Pyrazolone derivatives Phenazone Metamizaole Aminophenazone
48 (6) Cytostatic Drugs Antineoplastic agents used to treat various forms of cancer. Fluorouracil (pyrimidine ring) Cladribine (purine ring) Methotrexate (antifolate) (pteridine ring)
49 (7) Anti-Histamine Drugs There are different H.Cs. act as antihistamines Promethazine Phenothiazine derivatives Hydroxyzine Piperazine analogues
50 (8) Psychoactive Drugs Psychotropic substance is chemical substance that acts primarily upon the central nervous system (CS) where it alters brain function. Ex: m-chlorophenylpiperazine derivatives Cl R Etroperidone R= R= efazodone
51 Treatment of hypertension (9) Antihypertensive Drugs Ex: Benzothiadiazine derivatives R H 2 O S O O S O H Chlorothiazide Flumethiazide R=Cl R=CF 3
52 Give the name and chemical structure presence in the following drugs
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