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Nomenclature of Heterocyclic Compounds

Dr. Solomon DereseSCH 40213 Nomenclature of Heterocyclic CompoundsDr. Solomon DereseSCH Solomon DereseSCH 40215n = 1,2,3, ..TheHantzsch-Widmannomenclatureisbasedo nthetype(Z)oftheheteroatom;theringsize(n )andnatureofthering, Solomon DereseSCH of the heteroatomThetypeofheteroatomisindicated byaprefixasshownbelowforcommonhetreroato ms:OOxaNAzaSThiaPPhosphaHetreroatomPrefi xDr. Solomon DereseSCH size (n) ,namelyirfromtri,etfromtetra,epfromhepta ,ocfromocta,onfromnona, sizeSuffixRing sizeSuffix3ir7ep4et8oc5ol9on6in10ecTable I:Stemstoindicatetheringsizeofheterocycl esDr. Solomon DereseSCH 40218 Ring sizeSaturatedUnsaturatedSaturated (With Nitrogen)3-irane-irine-iridine4-etane-et e-etidine5-olane-ole-olidine6-inane-ine7 -epane-epine8-ocane-ocine9-onane-onine10 -ecane- Solomon DereseSCH , a Solomon DereseSCH 40220 Saturated3,4&5-memberednitrogenheterocyc lesshoulduserespectivelythetraditional"i ridine","etidine"&"olidine" ,suchas"dih

When naming such compounds the side of the heterocyclic ring is labeled by the letters a, b, c, etc., starting from the atom numbered 1. Therefore side

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Transcription of Nomenclature of Heterocyclic Compounds

1 Dr. Solomon DereseSCH 40213 Nomenclature of Heterocyclic CompoundsDr. Solomon DereseSCH Solomon DereseSCH 40215n = 1,2,3, ..TheHantzsch-Widmannomenclatureisbasedo nthetype(Z)oftheheteroatom;theringsize(n )andnatureofthering, Solomon DereseSCH of the heteroatomThetypeofheteroatomisindicated byaprefixasshownbelowforcommonhetreroato ms:OOxaNAzaSThiaPPhosphaHetreroatomPrefi xDr. Solomon DereseSCH size (n) ,namelyirfromtri,etfromtetra,epfromhepta ,ocfromocta,onfromnona, sizeSuffixRing sizeSuffix3ir7ep4et8oc5ol9on6in10ecTable I:Stemstoindicatetheringsizeofheterocycl esDr. Solomon DereseSCH 40218 Ring sizeSaturatedUnsaturatedSaturated (With Nitrogen)3-irane-irine-iridine4-etane-et e-etidine5-olane-ole-olidine6-inane-ine7 -epane-epine8-ocane-ocine9-onane-onine10 -ecane- Solomon DereseSCH , a Solomon DereseSCH 40220 Saturated3,4&5-memberednitrogenheterocyc lesshoulduserespectivelythetraditional"i ridine","etidine"&"olidine" ,suchas"dihydro"or"tetrahydro".

2 Dr. Solomon DereseSCH 40221 ExamplesOxa+irane= OxiraneAza+iridine= AziridineOxa+etane=OxetaneAza+etidine=Az etidineOxa+olane= OxolaneAza+olidine= AzolidineThia+irane= ThiiraneThia+etane=ThietaneThia+olane= ThiolaneDr. Solomon DereseSCH 40222 AzinaneAzinePyridineDr. Solomon DereseSCH 40223 Incaseofsubstituents,theheteroatomisdesi gnatednumber1, Solomon DereseSCH Solomon DereseSCH 40225 Partial UnsaturationUsefullyunsaturatednamewithd ihydro,tetrahydro,etcAzepine2,3-Dihydroa zepine4,5-Dihydroazepine2,5-Dihydroazepi ne12HN3Dr. Solomon DereseSCH 402261-Ethyl-4-methyl-4,5-dihydroazepine 1-Ethyl-5-methyl-2,3,4,5-tetrahydroazepi neNNWhen numbering give priority to saturated Solomon DereseSCH 40227 OOxaNAzaSThiaPPhosphaHetreroatomPrefixRi ng sizeSaturatedUnsaturatedSaturated (With Nitrogen)3-irane-irine-iridine4-etane-et e-etidine5-olane-ole-olidine6-inane-ine7 -epane-epine8-ocane-ocine9-onane-onine10 -ecane-ecineType (Z) -PrefixSize (n) -SuffixNature of ring -EndingRevisionDr.

3 Solomon DereseSCH 40228 Rings With More Than One HeteroatomDr. Solomon DereseSCH 40229 Twoormoresimilaratomscontainedinaringare indicatedbytheprefixes di- , tri , ,3,5-TriazineIfmorethanoneheteroatomoccu rinthering,thentheheterocycleisnamedbyco mbiningtheappropriateprefixeswiththeendi nginTableIinorderoftheirpreference,O>S> Solomon DereseSCH 40230 Oxaziridine1,3-Thiazole (Thiazole)1,4-Oxazine3-chloro-5-methyl-1 ,2,4-oxadiazoleDr. Solomon DereseSCH 40231 OSSeNBPCP riority of heteroatoms for numbering purposes:HighestLowestDr. Solomon DereseSCH ,3-thiazoleDr. Solomon DereseSCH Solomon DereseSCH 40234 OOCoumarinNIsoquinolineDr.

4 Solomon DereseSCH 402351,4-Dihydropyridine2,3-Dihydropyrid ineDr. Solomon DereseSCH 40236 Identical systems connected by a single bondSuchcompoundsaredefinedbytheprefixes bi-,tert-,quater-,etc.,accordingtothenum berofsystems,andthebondingisindicatedasf ollows:122 1 123 1 1 2 2 4 2,2' -Bipyridine2,2': 4',3'' -TerthiopheneDr. Solomon DereseSCH 40237 Naming Hetrocycleswith fused ringsWhennamingsuchcompoundsthesideofthe heterocyclicringislabeledbythelettersa,b ,c,etc., a beingbetweenatoms1and2,side b betweenatoms2and3, Solomon DereseSCH o , ,benzo, [b] furanBenzo[b] pyridineBenzo[c] thiopheneabcababDr. Solomon DereseSCH 40239cabdBenzo[d] thiepineDr.

5 Solomon DereseSCH 40240 Inaheterocyclicring,otherthingsbeingequa l, Solomon DereseSCH 40241 Handling the Extra Hydrogen Dr. Solomon DereseSCH bonds @ 2 and 4 Double bonds @ 2 and 5 Double bonds @ 2 and 4 Double bonds @ 1 and 4 Double bonds @ 1 and 3 Therefore, should have different Solomon DereseSCH 40243 Thisisaspecialproblemresultingfromisomer isminthepositionofthedoublebondswhichiss ometimesreferredtoas extra-hydrogen andthiscanbeaddressedbysimplyaddingapref ixthatindicatesthenumberoftheringatomtha tpossessesthehydrogenusingitaliccapital 1H 2H 3H , saturated position takes priority in Solomon DereseSCH 402444-Methyl-2H-oxete123412342-Methyl-2 H-oxete1H-Pyrrole(Pyrrole)3H-Pyrrole2H-P yrroleDr.

6 Solomon DereseSCH 40245Dr. Solomon DereseSCH 40246 Inreplacementnomenclature,theheterocycle 'snameiscomposedofthecarbocycle' ,"aza","oxa",and"thia"areprefixesforanit rogenringatom,anoxygenringatom,andasulfu rringatom, Solomon DereseSCH 40247 NNH2-Methylazacyclohexaneor2-Methylpiper idineN-EthylazacyclopentaneN-Ethylpyrrol idineorDr. Solomon DereseSCH 40248


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