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Heterocyclic Compounds

Heterocyclic compounds are a class of compounds that consist of carbon atoms and non-carbon atoms altogether forming a cyclic skeletal structure. These non-carbon atoms are collectively referred to as a heteroatom. The common heteroatoms include nitrogen, oxygen, and sulfur. Lactones, lactams, cyclic ethers that we’ve already learned are heterocyclic compounds. With similar properties of congeneric open-chain compounds, they will be discussed in corresponding chapters. This chapter will mainly discuss heterocyclic compounds with relatively stable ring system and with a certain degree of aromaticity, also known as aromatic heterocyclic compound.

There are many kinds and a large number of heterocyclic compounds widely distributed in nature. Many natural heterocyclic compounds in animals and plants play an important physiological role in the body. For example, heterocyclic structure exists in chlorophyll in plants, hemoglobin in animal blood, alkaloids and glycosides as the active ingredient in herbs, some antibiotics and vitamins, certain composition of amino acids in protein and bases in nucleotide. About half of the existing medicines have heterocyclic structures. Thus, heterocyclic compounds play an important role in organic compounds especially in organic medicines.

The most common and also the most important heterocyclic compounds are that with five-membered or six-membered heterocyclic ring and their fused heterocyclic compounds. Therefore, according to the size of the ring, heterocyclic compounds can be divided into five-membered compounds and six-membered heterocyclic compounds. E.g., furan, thiophene, pyrrole, imidazole, triazole and their fused heterocyclic compounds, indole, benzimidazole and diphenylene-oxide are all five-membered heterocyclic compounds, while pyridine, pyrimidine and their fused heterocyclic compounds, quinoline and quinazoline are all six-membered heterocyclic compounds.

According to the number of hetero atoms, five-membered compounds and six-membered heterocyclic compounds can be divided into one-hetero-atom-containing heterocyclic compounds and two-hetero-atom-containing and several-hetero-atom-containing heterocyclic compounds. E.g., furan, thiophene, pyridine, indole, quinoline, dibenzofuran, etc. are one-hetero-atom-containing heterocyclic compounds; imidazole, pyrimidine, benzimidazole, quinazoline, etc. are two-hetero-atom-containing heterocyclic compounds; purine, comprising more than two hetero atoms, is a several-hetero-atom-containing heterocyclic compound. According to the form of the ring in the molecule, heterocyclic compounds can be divided into single-heterocyclic compounds and fused heterocyclic compounds. E.g., furan, pyridine, pyrimidine, imidazole, etc. are single-heterocyclic compounds and indole, quinoline, dibenzofuran, purines, etc. are fused heterocyclic compounds.

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Structure Chemical Name CAS MF
3-(2-HYDROXY-5-METHYLPHENYL)PYRAZOLE 3-(2-HYDROXY-5-METHYLPHENYL)PYRAZOLE 57148-86-4 C10H10N2O
1,3-DI-TERT-BUTYLBENZIMIDAZOLIUM CHLORIDE 1,3-DI-TERT-BUTYLBENZIMIDAZOLIUM CHLORIDE 946607-10-9 C15H23ClN2
N-[[(1,2,3,5,6,7-hexahydro-s-indacen-4-yl) amino]carbonyl]-1-(1-methylethyl)-1H-Pyrazole-3-sulfonamide N-[[(1,2,3,5,6,7-hexahydro-s-indacen-4-yl) amino]carbonyl]-1-(1-methylethyl)-1H-Pyrazole-3-sulfonamide 1995067-59-8 C19H24N4O3S
Pyrimidine,5,5'-(1,4-phenylene)bis- Pyrimidine,5,5'-(1,4-phenylene)bis- 174303-53-8 C14H10N4
1,2,4-Triazolo[4,3-c]pyrimidine, 5-chloro-8-iodo- 1,2,4-Triazolo[4,3-c]pyrimidine, 5-chloro-8-iodo- 2374137-45-6 C5 H2 Cl I N4
1H-Benzimidazole, 2-(3,5-dibromophenyl)- 1H-Benzimidazole, 2-(3,5-dibromophenyl)- 1242080-87-0 C13H8Br2N2
(3S,4R)-4-(3-fluorophenyl)-1-(2-methoxyethyl)pyrrolidin-3-aminedihydrochloride (3S,4R)-4-(3-fluorophenyl)-1-(2-methoxyethyl)pyrrolidin-3-aminedihydrochloride 1414567-41-1 C13H20ClFN2O
1-(4-fluoro-2-methylphenyl)pyrrolidine-2,4-dione 1-(4-fluoro-2-methylphenyl)pyrrolidine-2,4-dione 1537294-18-0 C11H10FNO2
AKOS BC-0114 AKOS BC-0114 373824-30-7 C12H18N2O
2H-Benzimidazol-2-one, 4-bromo-7-fluoro-1,3-dihydro- 2H-Benzimidazol-2-one, 4-bromo-7-fluoro-1,3-dihydro- 1388074-82-5 C7H4BrFN2O
1H-Benzimidazole-7-carboxylic acid, 5-bromo-, methyl ester 1H-Benzimidazole-7-carboxylic acid, 5-bromo-, methyl ester 1806517-50-9 C9H7BrN2O2
2-Pyrrolidinone, 3-bromo-1-(1,1-dimethylethyl)- 2-Pyrrolidinone, 3-bromo-1-(1,1-dimethylethyl)- 1343578-30-2 C8H14BrNO
1,1'-((2,3,5,6-tetramethyl-1,4-phenylene)bis(methylene))bis(1H-imidazole) 1,1'-((2,3,5,6-tetramethyl-1,4-phenylene)bis(methylene))bis(1H-imidazole) 1012075-54-5 C18H22N4
4-OXAZOLEMETHANOL, 2-METHYL- 4-OXAZOLEMETHANOL, 2-METHYL- 141567-53-5 C5H7NO2
5-PYRIDIN-3-YLTHIOPHEN-2-AMINE 5-PYRIDIN-3-YLTHIOPHEN-2-AMINE 837376-58-6 C9H8N2S
2,4(1H,3H)-Pyrimidinedione, 1-(4-bromo-3-fluorophenyl)dihydro- 2,4(1H,3H)-Pyrimidinedione, 1-(4-bromo-3-fluorophenyl)dihydro- 1515197-90-6 C10H8BrFN2O2
2,4(1H,3H)-Pyrimidinedione, 1-cyclobutyl- 2,4(1H,3H)-Pyrimidinedione, 1-cyclobutyl- 1797409-28-9 C8H10N2O2
ethyl pyrrolidine-1-propionate ethyl pyrrolidine-1-propionate 6317-35-7 C9H17NO2
4-(Octadecyloxy)-1,3-benzenediamine 4-(Octadecyloxy)-1,3-benzenediamine 155096-60-9 C24H44N2O
Tris([2,2'-bipyridine]-4,4'-diamine)ruthenium(II)dichloride Tris([2,2'-bipyridine]-4,4'-diamine)ruthenium(II)dichloride C30H30Cl2N12Ru
Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-4,5-dimethyl-2H-imidazol-2-ylidene}gold(I) Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-4,5-dimethyl-2H-imidazol-2-ylidene}gold(I) 1192141-66-4 C29H41AuClN2-
Pyrimidine, 4,6-dichloro-2-[(1E)-2-phenylethenyl]- Pyrimidine, 4,6-dichloro-2-[(1E)-2-phenylethenyl]- 934353-78-3 C12H8Cl2N2
tetrakis(imidazol-1-ylmethyl)methane tetrakis(imidazol-1-ylmethyl)methane 860026-77-3 C17H20N8
2-iodo-1-p-tolyl-propan-1-one 2-iodo-1-p-tolyl-propan-1-one 236117-38-7 C10H11IO
5-Iodo-1-methyl-1H-pyrazole-4-carbaldehyde 5-Iodo-1-methyl-1H-pyrazole-4-carbaldehyde 1346818-72-1 C5H5IN2O
2-chloro-4-methyl-6-(pyrrolidin-1-yl)pyrimidine 2-chloro-4-methyl-6-(pyrrolidin-1-yl)pyrimidine 425425-25-8 C9H12ClN3
3-Benzyl-5-phenyl-3H-imidazol-4-ylamine 3-Benzyl-5-phenyl-3H-imidazol-4-ylamine 1000932-31-9 C16H15N3
4-CYANOPYRAZOLE 4-CYANOPYRAZOLE 31108-57-3 C4H3N3
1-Benzyl-1-methyl-4-oxopiperidinium iodide 1-Benzyl-1-methyl-4-oxopiperidinium iodide 77542-27-9 C13H18INO
1-tert-Butyl 6-ethyl 2,3-dihydro-1H-imidazo[1,2-b]pyrazole-1,6-dicarboxylate 1-tert-Butyl 6-ethyl 2,3-dihydro-1H-imidazo[1,2-b]pyrazole-1,6-dicarboxylate 1820647-54-8 C13H19N3O4
4,6-DICHLORONICOTINONITRILE 4,6-DICHLORONICOTINONITRILE 166526-03-0 C6H2Cl2N2
1-(tributylstannyl)-1H-imidazole 1-(tributylstannyl)-1H-imidazole 27605-35-2 C15H30N2Sn
5-[(3-ethylnaphth[2,1-d]oxazol-2(3H)-ylidene)ethylidene]-3-heptyl-1-phenyl-2-thioxoimidazolidin-4-one 5-[(3-ethylnaphth[2,1-d]oxazol-2(3H)-ylidene)ethylidene]-3-heptyl-1-phenyl-2-thioxoimidazolidin-4-one 13242-16-5 C31H33N3O2S
Carbamic acid, [(1S)-3-chloro-2-oxo-1-[[(3S)-2-oxo-3-pyrrolidinyl]methyl]propyl]-, 1,1-dimethylethyl ester (9CI) Carbamic acid, [(1S)-3-chloro-2-oxo-1-[[(3S)-2-oxo-3-pyrrolidinyl]methyl]propyl]-, 1,1-dimethylethyl ester (9CI) 870153-92-7 C13H21ClN2O4
1-(2,2-diethoxyethyl)-1H-imidazole 1-(2,2-diethoxyethyl)-1H-imidazole 18999-43-4 C9H16N2O2
3,5-dichloro-2-(trichloromethyl)pyridine 3,5-dichloro-2-(trichloromethyl)pyridine 1128-16-1 C6H2Cl5N
ethyl 4-acetylphenylacetate ethyl 4-acetylphenylacetate 1528-42-3 C12H14O3
Imidazo[1,2-b]pyridazine, 6-chloro-8-fluoro- Imidazo[1,2-b]pyridazine, 6-chloro-8-fluoro- 2306272-97-7 C6H3ClFN3
Uridine 5'-(trihydrogen diphosphate), mono-alpha-d-glucopyranosyl ester, sodium salt Uridine 5'-(trihydrogen diphosphate), mono-alpha-d-glucopyranosyl ester, sodium salt 14656-80-5 C15H25N2NaO17P2
1-(2-chloroethyl)pyrrolidine-2,5-dione 1-(2-chloroethyl)pyrrolidine-2,5-dione 41212-96-8 C6H8ClNO2
4-methylimidazolidin-2-one 4-methylimidazolidin-2-one 6531-31-3 C4H8N2O
(R)-1-N-Boc-2-(hydroxymethyl)piperazine (R)-1-N-Boc-2-(hydroxymethyl)piperazine 169448-87-7 C10H20N2O3
6-(Pyrrolidin-1-yl)pyridine-2-carbonitrile 6-(Pyrrolidin-1-yl)pyridine-2-carbonitrile 160017-13-0 C10H11N3
(R)-4-iodo-1-(pyrrolidin-3-yl)-1H-pyrazole hydrochloride (R)-4-iodo-1-(pyrrolidin-3-yl)-1H-pyrazole hydrochloride 2828444-26-2 C7H11ClIN3
Pyrazolo[1,5-a]pyridine-3-carbonitrile, 4-fluoro- (ACI) Pyrazolo[1,5-a]pyridine-3-carbonitrile, 4-fluoro- (ACI) 2106691-83-0 C8H4FN3
endo-N-Phenzyl-endo-3-aminotropane endo-N-Phenzyl-endo-3-aminotropane 36795-88-7 C14H20N2
Thieno[3,2-d]pyrimidine, 4-methoxy-7-methyl- (9CI) Thieno[3,2-d]pyrimidine, 4-methoxy-7-methyl- (9CI) 676549-71-6 C8H8N2OS
Imidazo[1,2-a]pyridine, 3-fluoro-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Imidazo[1,2-a]pyridine, 3-fluoro-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2259877-52-4 C13H16BFN2O2
Imidazo[1,2-a]pyridine, 7-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Imidazo[1,2-a]pyridine, 7-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2628351-34-6 C13H16BFN2O2
1-(tert-butyl) 2-methyl (2S,4R)-4-((4,4''-diamino-5'-(4-aminophenyl)-[1,1':3',1''-terphenyl]-4'-yl)methoxy)pyrrolidine-1,2-dicarboxylate 1-(tert-butyl) 2-methyl (2S,4R)-4-((4,4''-diamino-5'-(4-aminophenyl)-[1,1':3',1''-terphenyl]-4'-yl)methoxy)pyrrolidine-1,2-dicarboxylate 2116475-70-6 C36H40N4O5
(4R)-1-BOC-4-METHYL-D-PROLINE
(4R)-1-BOC-4-METHYL-D-PROLINE 871727-77-4 C11H19NO4
3-iodo-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine dihydrochloride 3-iodo-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine dihydrochloride
5-Formylamino-1-(2-formyloxyethyl)pyrazole 5-Formylamino-1-(2-formyloxyethyl)pyrazole C7H9N3O3
	4-(Iodomethyl)tetrahydro-2H-pyran 4-(Iodomethyl)tetrahydro-2H-pyran 101691-94-5 C6H11IO
5-bromo-6-chloro-1H-pyrazolo[3,4-b]pyridine 5-bromo-6-chloro-1H-pyrazolo[3,4-b]pyridine 1784380-03-5 C6H3BrClN3
3-Hydroxymethylpyrrolidine 3-Hydroxymethylpyrrolidine 5082-74-6 C5H11NO
(1S,2S)-1,2-diphenyl-1-Pyrrolidineethanamine (1S,2S)-1,2-diphenyl-1-Pyrrolidineethanamine 1416133-22-6 C18H22N2
(R)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE (R)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE 110199-17-2 C10H11NS2
cis-1-(tert-butoxycarbonyl)-4-ethylpyrrolidine-3-carboxylic acid cis-1-(tert-butoxycarbonyl)-4-ethylpyrrolidine-3-carboxylic acid 1310731-87-3 C12H21NO4
1,5-Diazabicyclo[4.3.0]non-5-ene 1,5-Diazabicyclo[4.3.0]non-5-ene 3001-72-7 C7H12N2
THYMINE-METHYL-D3-6-D THYMINE-METHYL-D3-6-D 156054-85-2 C5H2D4N2O2
4-Methyl-1,2,4-triazole-3-thiol 4-Methyl-1,2,4-triazole-3-thiol 24854-43-1 C3H5N3S
5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE 5'-O-(4,4'-DIMETHOXYTRITYL)-2'-DEOXYCYTIDINE 76512-82-8 C30H31N3O6
(S)-(3-FLUOROPYRROLIDIN-3-YL)METHANOL (S)-(3-FLUOROPYRROLIDIN-3-YL)METHANOL 2089671-61-2 C5H10FNO
3-PIPERIDINYL(1-PYRROLIDINYL)METHANONE 3-PIPERIDINYL(1-PYRROLIDINYL)METHANONE 35090-94-9 C10H18N2O
1,2-DIMETHYL-4-NITRO-1H-IMIDAZOLE 1,2-DIMETHYL-4-NITRO-1H-IMIDAZOLE 13230-04-1 C5H7N3O2
1-(4-FLUOROPHENYL)-5-PHENYL-1H-PYRAZOLE 1-(4-FLUOROPHENYL)-5-PHENYL-1H-PYRAZOLE 299162-83-7 C15H11FN2
4-(Bromomethyl)-5-phenyl-1,3-oxazole 4-(Bromomethyl)-5-phenyl-1,3-oxazole 368869-94-7 C10H8BrNO
4-BROMO-7-METHOXY-1H-INDOLE 4-BROMO-7-METHOXY-1H-INDOLE 436091-59-7 C9H8BrNO
6'-Bromo-4-hydroxy-8'-methyl-2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-1',5'-dione 6'-Bromo-4-hydroxy-8'-methyl-2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-1',5'-dione 1849594-08-6 C13H15BrN2O3
6-Chloro-3,3-dimethyl-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione 6-Chloro-3,3-dimethyl-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione 1849591-66-7 C9H9ClN2O2
6-Ethyl-2-methylimidazo[2,1-b]thiazole-5-carboxylic acid 6-Ethyl-2-methylimidazo[2,1-b]thiazole-5-carboxylic acid 1131613-58-5 C9H10N2O2S
7-Ethyl-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid 7-Ethyl-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid 1501589-02-1 C11H12N2O2
Ethyl 2,4-dioxohexahydropyrimidine-5-carboxylate Ethyl 2,4-dioxohexahydropyrimidine-5-carboxylate 1428760-91-1 C7H10N2O4
N-[5-(4-bromophenyl)-6-chloro-4-pyrimidinyl]-N'-benzyl-sulfamide N-[5-(4-bromophenyl)-6-chloro-4-pyrimidinyl]-N'-benzyl-sulfamide 441797-42-8 C17H14BrClN4O2S
di(4-t-butyl)phenyliodonium 2-trifluoromethylbenzenesulfonate di(4-t-butyl)phenyliodonium 2-trifluoromethylbenzenesulfonate 229325-98-8 C34H36F6I2O6S2
2-Azetidinemethanamine 2-Azetidinemethanamine 103550-76-1 C4H10N2
2-((S)-1-acryloyl-4-(7-(8-methylnaphthalen-1-yl)-2-(((S)-1-methylpyrrolidin-2-yl)methoxy)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)piperazin-2-yl)acetonitrile 2-((S)-1-acryloyl-4-(7-(8-methylnaphthalen-1-yl)-2-(((S)-1-methylpyrrolidin-2-yl)methoxy)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)piperazin-2-yl)acetonitrile 2206736-04-9 C33H39N7O2
1-PHENYL-3-(TRIFLUOROMETHYL)PYRAZOLE 1-PHENYL-3-(TRIFLUOROMETHYL)PYRAZOLE 99498-65-4 C10H7F3N2
Tris-2,4,6-(2-pyrimidyl)-1,3,5-triazine Tris-2,4,6-(2-pyrimidyl)-1,3,5-triazine 60681-68-7 C15H9N9
4,5-DIMETHYL-1H-IMIDAZOLE-2-THIOL 4,5-DIMETHYL-1H-IMIDAZOLE-2-THIOL 1192-72-9 C5H8N2S
(2S,5S)-5-methylpyrrolidine-2-carboxylic acid hydrochloride (2S,5S)-5-methylpyrrolidine-2-carboxylic acid hydrochloride 38228-14-7 C6H12ClNO2
[2-[(3R,4S)-4-ethyl-1-[(phenylmethoxy)carbonyl]-3-pyrrolidinyl]-2-oxoethyl]dimethyl-Sulfoxonium inner salt [2-[(3R,4S)-4-ethyl-1-[(phenylmethoxy)carbonyl]-3-pyrrolidinyl]-2-oxoethyl]dimethyl-Sulfoxonium inner salt 2050038-78-1 C18H25NO4S
Tolytriazole sodium salt Tolytriazole sodium salt 64665-57-2 C7H6N3Na
1-(4-Nitrobenzyl)-1H-imidazole 1-(4-Nitrobenzyl)-1H-imidazole 18994-90-6 C10H9N3O2
(2-METHYLIMIDAZO[1,2-A]PYRIDIN-3-YL)METHANOL (2-METHYLIMIDAZO[1,2-A]PYRIDIN-3-YL)METHANOL 30489-44-2 C9H10N2O
ETHYL IMIDAZO[2,1-B][1,3]BENZOTHIAZOLE-2-CARBOXYLATE ETHYL IMIDAZO[2,1-B][1,3]BENZOTHIAZOLE-2-CARBOXYLATE 64951-05-9 C12H10N2O2S
BENZOTRIAZOLE, SODIUM SALT BENZOTRIAZOLE, SODIUM SALT 15217-42-2 C6H6N3Na
8-NITROIMIDAZO[1,2-A]PYRIDINE 8-NITROIMIDAZO[1,2-A]PYRIDINE 52310-46-0 C7H5N3O2
2,5-Dimethoxytetrahydrofuran 2,5-Dimethoxytetrahydrofuran 696-59-3 C6H12O3
6-METHYL-3H-BENZOTHIAZOL-2-ONE 6-METHYL-3H-BENZOTHIAZOL-2-ONE 53827-53-5 C8H7NOS
5-CHLORO-1,3-DIMETHYLPYRAZOLE 5-CHLORO-1,3-DIMETHYLPYRAZOLE 54454-10-3 C5H7ClN2
2,3,3-Trimethylindolenine 2,3,3-Trimethylindolenine 1640-39-7 C11H13N
5,5'-(5-aminopyrimidine-4,6-diyl)diisophthalic acid 5,5'-(5-aminopyrimidine-4,6-diyl)diisophthalic acid 1980832-02-7 C20H13N3O8
1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl-2,2,3,3-d4)-2-(octylamino)-3-(pyrrolidin-1-yl)propan-1-ol 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl-2,2,3,3-d4)-2-(octylamino)-3-(pyrrolidin-1-yl)propan-1-ol
4,4'-bis(4-methyl-1H-imidazol-1-yl)-1,1'-biphenyl 4,4'-bis(4-methyl-1H-imidazol-1-yl)-1,1'-biphenyl 1789726-52-8 C20H18N4
1H-Imidazole-2-carboxylic acid, 1-(1-methylethyl)-, ethyl ester 1H-Imidazole-2-carboxylic acid, 1-(1-methylethyl)-, ethyl ester 2017188-77-9 C9H14N2O2
Ethanol, 2-[[(3aR,4S,6R,6aS)-6-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino]-5-(propylsulfonyl)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]- Ethanol, 2-[[(3aR,4S,6R,6aS)-6-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino]-5-(propylsulfonyl)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]- 1863036-51-4 C26H32F2N6O6S
Pyrrolidine, 3-(4-chlorophenyl)-3-methyl- Pyrrolidine, 3-(4-chlorophenyl)-3-methyl- 1250837-90-1 C11H14ClN
4-CHLORO-2-HYDROXYQUINOLINE 4-CHLORO-2-HYDROXYQUINOLINE 20146-59-2 C9H6ClNO
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