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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
(S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE (S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE 118949-61-4 C17H23N3O2
6-CHLORO-4-NITRO-1H-INDAZOLE 6-CHLORO-4-NITRO-1H-INDAZOLE 885519-50-6 C7H4ClN3O2
3-tert-Butoxycarbonylphenylboronic acid 3-tert-Butoxycarbonylphenylboronic acid 220210-56-0 C11H15BO4
Phosphonium, [(3'R)-1'-[(1,1-dimethylethoxy)carbonyl]-2-oxo[1,3'-bipyrrolidin]-3-yl]triphenyl-, bromide Phosphonium, [(3'R)-1'-[(1,1-dimethylethoxy)carbonyl]-2-oxo[1,3'-bipyrrolidin]-3-yl]triphenyl-, bromide 376653-42-8 C31H36BrN2O3P
4,4'-Difluorodiphenylketone-3,3'-disulfonic acid 4,4'-Difluorodiphenylketone-3,3'-disulfonic acid 625392-06-5 C13H8F2O7S2
7'-brmomspiro[fluorene-9,5'-indeno[1,2-b]pyridine] 7'-brmomspiro[fluorene-9,5'-indeno[1,2-b]pyridine] 1666128-76-2 C24H14BrN
5-bromo-4-chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine 5-bromo-4-chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine 1477532-48-1 C7H3BrClN3O2
8-Ethyl-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-8H-pyrido[2,3-d]pyrimidin-7-one 8-Ethyl-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-8H-pyrido[2,3-d]pyrimidin-7-one 211245-14-6 C20H24N6O
(3S,5R)-5-methylpyrrolidin-3-ol hydrochloride (3S,5R)-5-methylpyrrolidin-3-ol hydrochloride 1107658-78-5 C5H12ClNO
(R)-4-(2-chloro-6-(methylthiomethyl)pyrimidin-4-yl)-3-methylmorpholine (R)-4-(2-chloro-6-(methylthiomethyl)pyrimidin-4-yl)-3-methylmorpholine 1352227-15-6 C11H16ClN3OS
2-(5-(4-amino-2-fluoro-5-nitro-3-(tetrahydrofuran-2-yl)phenyl)pyrimidin-2-yl)propan-2-ol 2-(5-(4-amino-2-fluoro-5-nitro-3-(tetrahydrofuran-2-yl)phenyl)pyrimidin-2-yl)propan-2-ol 1384984-28-4 C17H19FN4O4
5-bromo-2-hydrazinylpyridine hydrochloride 5-bromo-2-hydrazinylpyridine hydrochloride 1295647-30-1 C5H7BrClN3
3,3-DIMETHYLPYRROLIDINE-2-CARBOXYLIC ACID hydrochloride 3,3-DIMETHYLPYRROLIDINE-2-CARBOXYLIC ACID hydrochloride 61406-78-8 C7H14ClNO2
6-Bromoindole-3-carboxylic acid 6-Bromoindole-3-carboxylic acid 101774-27-0 C9H6BrNO2
4-Bromo-1,3,5-trimethyl-1H-pyrazole 4-Bromo-1,3,5-trimethyl-1H-pyrazole 15801-69-1 C6H9BrN2
2-Boc-3,4-dihydro-1H-pyrrolo-[1,2-a]pyrazine-6-carboxylic acid 2-Boc-3,4-dihydro-1H-pyrrolo-[1,2-a]pyrazine-6-carboxylic acid 1363380-86-2 C13H18N2O4
(S)-3-(PYRROLIDIN-2-YL)PYRIDINE DIHYDROCHLORIDE (S)-3-(PYRROLIDIN-2-YL)PYRIDINE DIHYDROCHLORIDE 287966-92-1 C9H14Cl2N2
3-(difluoromethyl)pyrrolidine hydrochloride 3-(difluoromethyl)pyrrolidine hydrochloride 1376176-56-5 C5H10ClF2N
1,1'-bis(4-cyanophenyl)-[4,4'-bipyridine]-1,1'-diium chloride 1,1'-bis(4-cyanophenyl)-[4,4'-bipyridine]-1,1'-diium chloride 31515-20-5 C24H16ClN4+
6-AMino-1-isobutyl-3-Methyl-5-nitroso-2,4-pyriMidinedione 6-AMino-1-isobutyl-3-Methyl-5-nitroso-2,4-pyriMidinedione 54052-67-4 C9H14N4O3
tetrahydro-4-hydroxy-6-isopropyl-5,5-dimethyl-1H-pyrimidin-2-one tetrahydro-4-hydroxy-6-isopropyl-5,5-dimethyl-1H-pyrimidin-2-one 14068-64-5 C9H18N2O2
methyl (S)-2,5-dioxooxazolidine-4-propionate methyl (S)-2,5-dioxooxazolidine-4-propionate 1663-47-4 C7H9NO5
4-[2-(methylthio)ethyl]oxazolidine-2,5-dione 4-[2-(methylthio)ethyl]oxazolidine-2,5-dione 5840-77-7 C6H9NO3S
3-pyrrolidin-1-ylandrosta-3,5-dien-17-one 3-pyrrolidin-1-ylandrosta-3,5-dien-17-one 905-30-6 C23H33NO
3-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,5-a]pyrazine-1-carboxylic acid hydrochloride 3-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,5-a]pyrazine-1-carboxylic acid hydrochloride 2172053-56-2 C8H9ClF3N3O2
tetrahydro-1,3-bis(hydroxymethyl)-1H-pyrimidin-2-one tetrahydro-1,3-bis(hydroxymethyl)-1H-pyrimidin-2-one 3270-74-4 C6H12N2O3
4-ethyl-2-methyl-4,5-dihydrothiazole 4-ethyl-2-methyl-4,5-dihydrothiazole 4293-61-2 C6H11NS
[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl] hydrogen succinate [2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl] hydrogen succinate 13182-87-1 C10H13N3O6
(S)-2-(Methoxydiphenylmethyl)pyrrolidine (S)-2-(Methoxydiphenylmethyl)pyrrolidine 118971-03-2 C18H21NO
1-(azetidin-3-yl)-4-iodo-1H-pyrazole hydrochloride 1-(azetidin-3-yl)-4-iodo-1H-pyrazole hydrochloride
(S)-4-iodo-1-(pyrrolidin-3-yl)-1H-pyrazole hydrochloride (S)-4-iodo-1-(pyrrolidin-3-yl)-1H-pyrazole hydrochloride 2828444-29-5 C7H11ClIN3
2-Pyridinecarboxamide, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]amino]-1,2,5,6-tetrahydro-4-methyl-, (2S,5R)- 2-Pyridinecarboxamide, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]amino]-1,2,5,6-tetrahydro-4-methyl-, (2S,5R)- 2209874-05-3 C13H27N3O2Si
1-methyl-2-Pyrrolidonium tetrafluoroborate chloride 1-methyl-2-Pyrrolidonium tetrafluoroborate chloride 942068-29-3 C9H13N5
Imidazo[1,2-a]pyrazine, 5,6,7,8-tetrahydro-2-(trifluoromethyl)- (9CI) Imidazo[1,2-a]pyrazine, 5,6,7,8-tetrahydro-2-(trifluoromethyl)- (9CI) 126069-70-3 C7H8F3N3
Proline, 1-(2-cyanoethyl)- (9CI) Proline, 1-(2-cyanoethyl)- (9CI) 36901-89-0 C8H12N2O2
Carbamic acid, [(3R,4S)-4-fluoro-3-pyrrolidinyl]-, 1,1-dimethylethyl ester, rel- Carbamic acid, [(3R,4S)-4-fluoro-3-pyrrolidinyl]-, 1,1-dimethylethyl ester, rel- 169750-42-9 C9H17FN2O2
1-Octanoylbenzotriazole 1-Octanoylbenzotriazole 58068-80-7 C14H19N3O
2-CHLORO-3-IODO-5-PICOLINE 2-CHLORO-3-IODO-5-PICOLINE 59782-91-1 C6H5ClIN
2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl- (9CI) 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl- (9CI) 2417-22-3 C5H6N2O3
4-Pyrimidinecarbonitrile, 2-(dimethylamino)- (9CI) 4-Pyrimidinecarbonitrile, 2-(dimethylamino)- (9CI) 79605-00-8 C7H8N4
1H-BENZIMIDAZOL-7-AMINE 1H-BENZIMIDAZOL-7-AMINE 4331-29-7 C7H7N3
1-(tert-butyl) 2-methyl (2S,4R)-4-((4,4''-diamino-5'-(4-aminophenyl)-[1,1':3',1''-terphenyl]-4'-yl)oxy)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)oxy)pyrrolidine-1,2-dicarboxylate 2116475-69-3 C35H38N4O5
2-chloro-3-methoxy-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)pyridine 2-chloro-3-methoxy-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)pyridine
Chloro[1,3-bis(cyclohexyl)2H-imidazol-2-ylidene]gold(I), 98% Chloro[1,3-bis(cyclohexyl)2H-imidazol-2-ylidene]gold(I), 98% 852445-87-5 C15H24AuClN2
4,4'-((3',4',5',6'-tetrakis(4-(pyridin-4-ylethynyl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-diyl)bis(ethyne-2,1-diyl))dipyridine 4,4'-((3',4',5',6'-tetrakis(4-(pyridin-4-ylethynyl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-diyl)bis(ethyne-2,1-diyl))dipyridine 591215-25-7 C84H48N6
ffBTZ-C8-2Br ffBTZ-C8-2Br 1393528-97-6 C14H17Br2F2N3
4-Chloro-2-iodo-5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine 4-Chloro-2-iodo-5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine 1420885-94-4 C14H17ClF3IN2OSi
3,6-DI-4-PYRIDYL-1,2,4,5-TETRAZINE 3,6-DI-4-PYRIDYL-1,2,4,5-TETRAZINE 57654-36-1 C12H8N6
ETHYL 5-ACETYLISOXASOLE-3-CARBOXYLATE ETHYL 5-ACETYLISOXASOLE-3-CARBOXYLATE 104776-70-7 C8H9NO4
Poly-p-xylylene Poly-p-xylylene 25722-33-2
5-thien-2-yl-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-2-carbohydrazide 5-thien-2-yl-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-2-carbohydrazide 832739-24-9 C12H12F3N5OS
4,6-dibromo-2-methylpyrimidine 4,6-dibromo-2-methylpyrimidine 1598222-27-5 C5H4Br2N2
3-fluoro-4-(pyrrolidin-1-ylmethyl)benzaldehyde 3-fluoro-4-(pyrrolidin-1-ylmethyl)benzaldehyde 1443353-89-6 C12H14FNO
C-(1-BENZYL-PYRROLIDIN-3-YL)-METHYLAMINE C-(1-BENZYL-PYRROLIDIN-3-YL)-METHYLAMINE 93138-61-5 C12H18N2
3-(4-Pyridine)acrylic acid 3-(4-Pyridine)acrylic acid 84228-93-3 C8H7NO2
1-tert-Butyl-4-iodo-1H-pyrazole 1-tert-Butyl-4-iodo-1H-pyrazole 1354705-41-1 C7H11IN2
1-(azetidin-3-yl)-4-iodo-1H-pyrazole 1-(azetidin-3-yl)-4-iodo-1H-pyrazole 1343072-59-2 C6H8IN3
6-CHLORO-2-PHENYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID 6-CHLORO-2-PHENYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID 220465-51-0 C14H9ClN2O2
1,3-DIMETHYL-4-NITRO-1H-PYRAZOLE 1,3-DIMETHYL-4-NITRO-1H-PYRAZOLE 3920-38-5 C5H7N3O2
7-BROMO-1H-INDOLE-3-CARBALDEHYDE 7-BROMO-1H-INDOLE-3-CARBALDEHYDE 115666-21-2 C9H6BrNO
6-AZACYTOSINE 6-AZACYTOSINE 931-85-1 C3H4N4O
2-OXO-PYRROLIDINE-3-CARBOXYLIC ACID ETHYL ESTER 2-OXO-PYRROLIDINE-3-CARBOXYLIC ACID ETHYL ESTER 36821-26-8 C7H11NO3
3,5-DIMETHYL-4-NITROISOXAZOLE 3,5-DIMETHYL-4-NITROISOXAZOLE 1123-49-5 C5H6N2O3
Benzyl (2R,4S)-4-amino-2-methylpyrrolidine-1-carboxylate Benzyl (2R,4S)-4-amino-2-methylpyrrolidine-1-carboxylate 2165506-16-9 C13H18N2O2
6'-Bromo-8'-chloro-1',5'-dioxo-1',5'-dihydro-2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-4-carbonitrile 6'-Bromo-8'-chloro-1',5'-dioxo-1',5'-dihydro-2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-4-carbonitrile 1849593-46-9 C13H11BrClN3O2
5-[1-(hydroxyimino)ethyl]-4-methylpyrimidin-2-amine 5-[1-(hydroxyimino)ethyl]-4-methylpyrimidin-2-amine 1050886-14-0 C7H10N4O
2-BROMO-4-METHYL-1H-IMIDAZOLE 2-BROMO-4-METHYL-1H-IMIDAZOLE 23328-88-3 C4H5BrN2
1-(3,4,5-Trihydroxypentanoyl)-β-carboline 1-(3,4,5-Trihydroxypentanoyl)-β-carboline 180995-40-8 C16H16N2O4
(6-Methyl-1H-benzimidazol-2-yl)methanol (6-Methyl-1H-benzimidazol-2-yl)methanol 20034-02-0 C9H10N2O
4-(2-bromoethyl)pyridine hydrobromide 4-(2-bromoethyl)pyridine hydrobromide 120277-01-2 C7H9Br2N
1-{[(tert-butoxy)carbonyl]amino}-5-oxopyrrolidine-3-carboxylic acid 1-{[(tert-butoxy)carbonyl]amino}-5-oxopyrrolidine-3-carboxylic acid 1354952-07-0 C10H16N2O5
Terevalefim Terevalefim 1070881-42-3 C9H8N2S
1,3-DIMETHYL-1H-PYRAZOLE-5-CARBONITRILE 1,3-DIMETHYL-1H-PYRAZOLE-5-CARBONITRILE 306936-77-6 C6H7N3
2-{5H,6H,7H,8H,9H-[1,2,4]triazolo[4,3-a]azepin-3-yl}pyrrolidine 2-{5H,6H,7H,8H,9H-[1,2,4]triazolo[4,3-a]azepin-3-yl}pyrrolidine 923690-18-0 C11H18N4
4-chloro-6-(2,2,2-trifluoroethyl)thieno[3,2-d]pyrimidine 4-chloro-6-(2,2,2-trifluoroethyl)thieno[3,2-d]pyrimidine 2102553-51-3 C8H4ClF3N2S
Fluclotizolam Fluclotizolam 54123-15-8 C15H10ClFN4S
4-Pyrimidinamine, 5,6-dichloro-N-methyl- 4-Pyrimidinamine, 5,6-dichloro-N-methyl- 1428252-93-0 C5H5Cl2N3
2-(6-Methoxy-naphthalen-1-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 2-(6-Methoxy-naphthalen-1-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 588717-94-6 C17H21BO3
(2,5-dioxopyrrolidin-1-yl) (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(phenylmethoxycarbonylamino)pentanoate (2,5-dioxopyrrolidin-1-yl) (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(phenylmethoxycarbonylamino)pentanoate 57225-26-0 C22H29N3O8
Ethyl 1-Methyl-2,4-dioxo-1H,2H,3H,4H-pyrido[2,3-d]pyrimidine-7-carboxylate Ethyl 1-Methyl-2,4-dioxo-1H,2H,3H,4H-pyrido[2,3-d]pyrimidine-7-carboxylate 1000932-39-7 C11H11N3O4
5-(Benzyloxy)-1,2-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid 5-(Benzyloxy)-1,2-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid 389130-68-1 C14H14N2O4
4-(propan-2-yl)pyrimidin-5-amine dihydrochloride 4-(propan-2-yl)pyrimidin-5-amine dihydrochloride 2241139-74-0 C7H12ClN3
1,3-Dioxolane 1,3-Dioxolane 646-06-0 C3H6O2
5-ISOXAZOLEMETHANOL 5-ISOXAZOLEMETHANOL 98019-60-4 C4H5NO2
Boron trifluoride tetrahydrofuran complex Boron trifluoride tetrahydrofuran complex 462-34-0 C4H8BF3O
Oxazole-4-carbonitrile Oxazole-4-carbonitrile 55242-84-7 C4H2N2O
PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE 159326-68-8 C6H6N4
OXOTREMORINE SESQUIFUMARATE OXOTREMORINE SESQUIFUMARATE 17360-35-9 C36H48N4O14
2,4,4-TRIMETHYL-2-OXAZOLINE 2,4,4-TRIMETHYL-2-OXAZOLINE 1772-43-6 C6H11NO
Fenoxazoline Fenoxazoline
Midodrine hydrochloride Midodrine hydrochloride 3092-17-9 C12H19ClN2O4
P-(2-BENZOXAZOLYL)BENZYL CHLORIDE P-(2-BENZOXAZOLYL)BENZYL CHLORIDE 57864-19-4 C14H10ClNO
6-methyl-1H-indole-2,3-dione 6-methyl-1H-indole-2,3-dione 1128-44-5 C9H7NO2
5-Chloro-2-methoxy-4-methylpyridine 5-Chloro-2-methoxy-4-methylpyridine 851607-29-9 C7H8ClNO
3-IODO-4-METHOXY-PYRIDINE 3-IODO-4-METHOXY-PYRIDINE 89640-55-1 C6H6INO
1H-Benzimidazole,5-chloro-2-propyl-(9CI) 1H-Benzimidazole,5-chloro-2-propyl-(9CI) 4887-91-6 C10H11ClN2
7H-Pyrrolo[1,2-c]imidazol-7-one,5,6-dihydro-(9CI) 7H-Pyrrolo[1,2-c]imidazol-7-one,5,6-dihydro-(9CI) 426219-43-4 C6H6N2O
1H-Benzimidazol-2-amine,5-chloro-6-fluoro-(9CI) 1H-Benzimidazol-2-amine,5-chloro-6-fluoro-(9CI) 142356-64-7 C7H5ClFN3
1H-Imidazole-5-carboxylicacid,1-(1-methylethyl)-(9CI) 1H-Imidazole-5-carboxylicacid,1-(1-methylethyl)-(9CI) 105293-81-0 C7H10N2O2
4-CHLORO-2-PHENYLQUINAZOLINE 4-CHLORO-2-PHENYLQUINAZOLINE 6484-25-9 C14H9ClN2
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