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Heterocycles: Heterocyclic Nomenclature
Heterocycles: Heterocyclic Nomenclature
Heterocycles: Heterocyclic Nomenclature
Chem 6352
Not all heterocyclic rings follow the Hantzsch-Widman rules listed above, typically because they have
established common names. These trivial names typically show traces of the systematic nomenclature,
but do not completely follow the rules.
Heterocycles
H O
H H
O S N N N O S HN HN
NH N N
oxirane/ thiirane aziridine azirine diaziridine diazirine oxetane thietane azetidine !-lactam
epoxide
H H H
O O S S N N N N
O
O O S N N N
S H H
benzofuran coumaran isobenzofuran benzothiophene dibenzothiophene indoline indole indolinine
(uncommon)
O O
O O NH
N N
N N N
H H H N
H
oxindole indoxyl isatin isoindole indolizine pyrrolizine carbazole
O
H H
N N N N N
O O S S O NH O NH O N O S N S HN NH HN N HN N HN HN N
dioxolane dithiolane oxazolidine oxazolidinone oxazole isoxazole thiazole isothiazole imidazolidine 2-imidazoline imidazole pyrazolidine 2-pyrazoline pyrazole
N N N
O N N
N N
N N N
O O O S N
H H H
benzodioxole benzoxazole indoxazine benzothiazole benzimidazole 1H-indazole purine
S N N N
N N
O N HN N HN N N N
N N N N
N N N NH H N N
1,2,3-oxadiazole 1,3,4-thiadiazole 1,2,3-triazole 1,2,4-triazole tetrazole benzotriazole quinuclidine diazabicyclooctane diazabicycloundecane
DABCO DBU
H H
O O O O N N N N N O
N
N
Tetrahydropyran Dihydropyran 4H-pyran 2H-pyran piperidine pyridine picoline lutidine collidine pyridone acridine
THP DHP
O
O
N N N
O O O O N N N O
H H
chromene coumarin isocoumarin xanthene tetrahydroquinoline quinoline isoquinoline quinolone 4H-quinolizine quinolizinium
O S H
O S N N N N N
O O S S S S N N N
N N N N N N N
O O S S N N
H H H
1,4-dioxane morpholine paraformaldehyde 1,4-dithiane 1,3-dithiane thiomorpholine trithiane piperazine pyrazine pyrimidine pyridazine 1,3,5-triazine tetrazine
N
N N N
N N N
N N N N N N N N
N H
1,8-naphthyridine quinoxaline quinazoline cinnoline phthalazine !-carboline bipyridyl
cyclazine julolidine
O S H
N N N
N
O S NH
N N N N N
H H N
phenoxazine phenothiazine phenazine pteridine oxepine thiepin azepine benzodiazepine
Examples of Biologically Relevant Heterocycles
O O NH 2 O NH 2
O
HN HN N HN NH N N
NH 2 N
O N O N O N O N O H 2N N NH 2
N N H H H H
niacin nicotine thymine uracil cytosine cyanuric acid melamine
NH 2 O O O
H H H
N N N N
N HN N HN
O
N N O N N O N N
N H 2N N H
H
adenine guanine caffeine uric acid
CO2H
NH 2 HO NH 2 O NH 2
N N N
H H H
tryptophan serotonin melatonin
Et 2N N
N N
H H
NH HN NH HN
H H
N N
N
H
lysergic acid diethyl amide porphyrinogen porphyrin
LSD