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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
Formamide, N-1H-benzimidazol-4-yl- (9CI) Formamide, N-1H-benzimidazol-4-yl- (9CI) 137654-47-8 C8H7N3O
(2S,4S)-4-fluoro-2-methylpyrrolidine hydrochloride (2S,4S)-4-fluoro-2-methylpyrrolidine hydrochloride 2828444-34-2 C5H11ClFN
2-pyridin-2-ylpyrimidine-5-carboxylic acid 2-pyridin-2-ylpyrimidine-5-carboxylic acid 933988-22-8 C10H7N3O2
Pyrimidine, 5-(bromomethyl)-2-(trifluoromethyl)- (9CI) Pyrimidine, 5-(bromomethyl)-2-(trifluoromethyl)- (9CI) 198404-35-2 C6H4BrF3N2
2,5-Dimethyl-1H-imidazole-4-carboxaldehyde 2,5-Dimethyl-1H-imidazole-4-carboxaldehyde 68282-52-0 C6H8N2O
2-triisopropylsilyl oxazole 2-triisopropylsilyl oxazole 433332-27-5 C12H23NOSi
Domazoline Domazoline 6043-01-2 C14H20N2O2
1-METHYL-4-(TRIFLUOROMETHYL)-1H-IMIDAZOLE-2-CARBOXYLIC ACID 1-METHYL-4-(TRIFLUOROMETHYL)-1H-IMIDAZOLE-2-CARBOXYLIC ACID 1554401-44-3 C6H5F3N2O2
N-BOC-4-Hydroxypiperidine N-BOC-4-Hydroxypiperidine 109384-19-2 C10H19NO3
4,5-DIPHENYL-2-MERCAPTOOXAZOLE 4,5-DIPHENYL-2-MERCAPTOOXAZOLE 6670-13-9 C15H11NOS
2-CHLOROADAMANTANE 2-CHLOROADAMANTANE 7346-41-0 C10H15Cl
(2S,4S)-4-Fluoro-2-(Fluoromethyl)Pyrrolidine Hydrochloride(WX601106) (2S,4S)-4-Fluoro-2-(Fluoromethyl)Pyrrolidine Hydrochloride(WX601106) 1951424-95-5 C5H10ClF2N
2-Bromo-4,5-dichloro-1H-imidazole 2-Bromo-4,5-dichloro-1H-imidazole 16076-27-0 C3HBrCl2N2
1-Boc-4-(aminomethyl)piperidine 1-Boc-4-(aminomethyl)piperidine 144222-22-0 C11H22N2O2
TERT-BUTYL 4-CYANO-2,2-DIMETHYL-3-OXOPYRROLIDINE-1-CARBOXYLATE TERT-BUTYL 4-CYANO-2,2-DIMETHYL-3-OXOPYRROLIDINE-1-CARBOXYLATE 718632-42-9 C12H18N2O3
3-(4-NITROPHENYL)PYRAZOLE 3-(4-NITROPHENYL)PYRAZOLE 20583-31-7 C9H7N3O2
3-Nitro-1,2,4-triazole 3-Nitro-1,2,4-triazole 24807-55-4 C2H2N4O2
1-Methyl-1H-imidazole-5-carbonyl chloride hydrochloride 1-Methyl-1H-imidazole-5-carbonyl chloride hydrochloride 343569-06-2 C5H6Cl2N2O
(S)-(+)-2-(ANILINOMETHYL)PYRROLIDINE (S)-(+)-2-(ANILINOMETHYL)PYRROLIDINE 64030-44-0 C11H16N2
1-NITROPYRAZOLE 1-NITROPYRAZOLE 7119-95-1 C3H3N3O2
2-(2-(Pyridin-2-yl)-1H-imidazol-4-yl)ethan-1-amine dihydrochloride 2-(2-(Pyridin-2-yl)-1H-imidazol-4-yl)ethan-1-amine dihydrochloride 56624-07-8 C10H13ClN4
3-(1-Methylpropyl)pyrrolidine 3-(1-Methylpropyl)pyrrolidine 1087748-11-5 C8H17N
6'-Chloro-1'H-spiro[cyclopentane-1,3'-imidazo[1,5-a]pyridine]-1',5'(2'H)-dione 6'-Chloro-1'H-spiro[cyclopentane-1,3'-imidazo[1,5-a]pyridine]-1',5'(2'H)-dione 1849591-70-3 C11H11ClN2O2
7-Bromoimidazo[5,1-f][1,2,4]triazin-4(1H)-one 7-Bromoimidazo[5,1-f][1,2,4]triazin-4(1H)-one 1779924-85-4 C5H3BrN4O
9-(4'-chloro-[1,1'-biphenyl]-3-yl)-9H-carbazole 9-(4'-chloro-[1,1'-biphenyl]-3-yl)-9H-carbazole 2148296-04-0 C24H16ClN
2-AMINO-1-PYRROLIDIN-1-YL-ETHANONE HCL 2-AMINO-1-PYRROLIDIN-1-YL-ETHANONE HCL 35855-14-2 C6H13ClN2O
2,2,2-trifluoroethyl N-[2-(pyrrolidin-1-yl)pyridin-3-yl]carbamate hydrochloride 2,2,2-trifluoroethyl N-[2-(pyrrolidin-1-yl)pyridin-3-yl]carbamate hydrochloride 1311315-79-3 C12H15ClF3N3O2
4-BROMO-3-TRIFLUOROMETHYL-1H-PYRAZOLE 4-BROMO-3-TRIFLUOROMETHYL-1H-PYRAZOLE 19968-17-3 C4H2BrF3N2
(R)-2-(2,5-dichlorophenyl)pyrrolidine hydrochloride (R)-2-(2,5-dichlorophenyl)pyrrolidine hydrochloride 2241594-21-6 C10H12Cl3N
3-Methylpyrrolidine-3-carboxylic acid hydrochloride 3-Methylpyrrolidine-3-carboxylic acid hydrochloride 1222503-25-4 C6H12ClNO2
(S)-Pyrrolidin-2-ylbis(4-(trifluoromethyl)phenyl)methanol hydrochloride (S)-Pyrrolidin-2-ylbis(4-(trifluoromethyl)phenyl)methanol hydrochloride 131180-54-6 C19H18ClF6NO
5-Chloro-7-methoxypyrazolo[1,5-a]pyrimidine 5-Chloro-7-methoxypyrazolo[1,5-a]pyrimidine 1824286-23-8 C7H6ClN3O
5-BROMOURIDINE 5'-TRIPHOSPHATE SODIUM 5-BROMOURIDINE 5'-TRIPHOSPHATE SODIUM 161848-60-8 C9H15BrN2NaO15P3
ANTAZOLINE METHANESULFONATE ANTAZOLINE METHANESULFONATE 3131-32-6 C18H20N3O3S-
5,6-Diamino-1,3-dihydro-2H-benzoimidazol-2-one 5,6-Diamino-1,3-dihydro-2H-benzoimidazol-2-one 55621-49-3 C7H8N4O
3,5-dimethyl-1-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 3,5-dimethyl-1-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 2246602-45-7 C16H27BN2O3
(2α,3α,5α,16β,17β)-2,3-Epoxy-16-(1-pyrrolidinyl)androstan-17-ol (2α,3α,5α,16β,17β)-2,3-Epoxy-16-(1-pyrrolidinyl)androstan-17-ol 119302-19-1 C23H37NO2
4-[methylsulfanyl(morpholin-4-yl)phosphoryl]morpholine 4-[methylsulfanyl(morpholin-4-yl)phosphoryl]morpholine 141930-98-5 C9H19N2O3PS
5-(1-methyl-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-amine 5-(1-methyl-1H-imidazol-2-yl)-1,3,4-thiadiazol-2-amine 25306-10-9 C6H7N5S
2,4,6-tris(4-methylpyrazol-1-yl)-1,3,5-triazine 2,4,6-tris(4-methylpyrazol-1-yl)-1,3,5-triazine 154403-26-6 C15H15N9
2-(Bromomethyl)thieno[3,2-d]pyrimidine 2-(Bromomethyl)thieno[3,2-d]pyrimidine 77294-18-9 C7H5BrN2S
6-Bromo-7-ethoxyimidazo[1,2-a]pyridine 6-Bromo-7-ethoxyimidazo[1,2-a]pyridine 2141967-16-8 C9H9BrN2O
Fenoxazoline Fenoxazoline 4846-91-7 C13H18N2O
(2S,4R)-4-fluoro-2-methylpyrrolidine hydrochloride (2S,4R)-4-fluoro-2-methylpyrrolidine hydrochloride 2828444-35-3 C5H11ClFN
5-(4-FLUOROPHENYL)-2H-PYRAZOL-3-YLAMINE 5-(4-FLUOROPHENYL)-2H-PYRAZOL-3-YLAMINE 72411-52-0 C9H8FN3
2-AMINO-5-ETHYL-6-METHYLPYRIMIDIN-4-OL 2-AMINO-5-ETHYL-6-METHYLPYRIMIDIN-4-OL 28224-69-3 C7H11N3O
3-Nitro-1H-pyrazole 3-Nitro-1H-pyrazole 26621-44-3 C3H3N3O2
Oxazoline Oxazoline 27341-52-2 C3H5NO
2,4,5-TRIMETHYLOXAZOLE 2,4,5-TRIMETHYLOXAZOLE 20662-84-4 C6H9NO
Recombinant Human AICDA Protein Recombinant Human AICDA Protein
5-Bromo-2-phenylbenzimidazole 5-Bromo-2-phenylbenzimidazole 1741-50-0 C13H9BrN2
3H-Imidazo[4,5-c]pyridine, 6-bromo-4-chloro-3-(1-methylethyl)- 3H-Imidazo[4,5-c]pyridine, 6-bromo-4-chloro-3-(1-methylethyl)- 2416917-56-9 C9 H9 Br Cl N3
1,3-Pyrrolidinedicarboxylic acid, 2-methyl-4-oxo-, 1-(1,1-dimethylethyl) 3-ethyl ester 1,3-Pyrrolidinedicarboxylic acid, 2-methyl-4-oxo-, 1-(1,1-dimethylethyl) 3-ethyl ester 1229455-56-4 C13H21NO5
Pyridine, 4,4'-(2,3-dihydrothieno[3,4-b]-1,4-dioxin-5,7-diyl)bis- Pyridine, 4,4'-(2,3-dihydrothieno[3,4-b]-1,4-dioxin-5,7-diyl)bis- 1235864-74-0 C16H12N2O2S
4-CHLORO-7-NITROQUINAZOLINE 4-CHLORO-7-NITROQUINAZOLINE 19815-17-9 C8H4ClN3O2
(S)-ALPHA,ALPHA-BIS(4-METHYLPHENYL)-2-PYRROLIDINEMETHANOL (S)-ALPHA,ALPHA-BIS(4-METHYLPHENYL)-2-PYRROLIDINEMETHANOL 131180-52-4 C19H23NO
3-(4-AMINO-PHENYL)-PYRROLIDINE-2,5-DIONE 3-(4-AMINO-PHENYL)-PYRROLIDINE-2,5-DIONE 32856-49-8 C10H10N2O2
4-(HYDROXYMETHYL)-1-METHYLPYRROLIDIN-2-ONE 4-(HYDROXYMETHYL)-1-METHYLPYRROLIDIN-2-ONE 59887-20-6 C6H11NO2
4-CHLORO-5-IODO-7-METHYL-7H-PYRROLO[2,3-D]PYRIMIDINE 4-CHLORO-5-IODO-7-METHYL-7H-PYRROLO[2,3-D]PYRIMIDINE 833481-37-1 C7H5ClIN3
7-BROMO-1,5-DIHYDRO-4H-PYRROLO[3,2-D]PYRIMIDIN-4-ONE 7-BROMO-1,5-DIHYDRO-4H-PYRROLO[3,2-D]PYRIMIDIN-4-ONE 93587-23-6 C6H4BrN3O
4-BROMO-2-METHYL-1H-BENZIMIDAZOLE 4-BROMO-2-METHYL-1H-BENZIMIDAZOLE 20223-87-4 C8H7BrN2
7-BroMo-2,3-dihydro-1H-indole 7-BroMo-2,3-dihydro-1H-indole 62813-85-8 C8H8BrN
1-(METHOXYETHYL)-1-METHYLPYRROLIDINIUM BIS(TRIFLUOROMETHYLSULFONYL)IMIDE 1-(METHOXYETHYL)-1-METHYLPYRROLIDINIUM BIS(TRIFLUOROMETHYLSULFONYL)IMIDE 757240-24-7 C8H18NO.C2F6NO4S2
Ethyl 4-chlorothieno[2,3-d]pyrimidine-2-carboxylate Ethyl 4-chlorothieno[2,3-d]pyrimidine-2-carboxylate 1192540-11-6 C9H7ClN2O2S
1-(2-Chloroethyl)pyrrolidine Hydrochloride 1-(2-Chloroethyl)pyrrolidine Hydrochloride 7250-67-1 C6H13Cl2N
4-Chloro-6-methyl-1H-pyrazolo[3,4-d]pyrimidine 4-Chloro-6-methyl-1H-pyrazolo[3,4-d]pyrimidine 30129-53-4 C6H5ClN4
(3S,4R)-1-(tert-butoxycarbonyl)-4-(4-(trifluoromethyl)phenyl)pyrrolidine-3-carboxylic acid (3S,4R)-1-(tert-butoxycarbonyl)-4-(4-(trifluoromethyl)phenyl)pyrrolidine-3-carboxylic acid 955137-85-6 C17H20F3NO4
3-Tert-Butyl-1H-Pyrazol-4-carbaldehyde 3-Tert-Butyl-1H-Pyrazol-4-carbaldehyde 1001020-17-2 C8H12N2O
5-BROMO-2-CHLORO-BENZOXAZOLE 5-BROMO-2-CHLORO-BENZOXAZOLE 1030377-54-8 C7H3BrClNO
4-Methoxy-2-(trifluoromethyl)pyridine 4-Methoxy-2-(trifluoromethyl)pyridine 1065103-97-0 C7H6F3NO
3-bromo-5-fluoroimidazo[1,2-a]pyridine 3-bromo-5-fluoroimidazo[1,2-a]pyridine 1388711-44-1 C7H4BrFN2
1-(3-Bromo-4-methylphenyl)pyrrolidin-2-one 1-(3-Bromo-4-methylphenyl)pyrrolidin-2-one 1226225-33-7 C11H12BrNO
2-Bromomethyl-oxazole 2-Bromomethyl-oxazole 1065073-35-9 C4H4BrNO
1-N-acetyluracil 1-N-acetyluracil 40338-28-1 C6H6N2O3
7-AMINO-4(1H)-QUINAZOLINONE 7-AMINO-4(1H)-QUINAZOLINONE 90004-09-4 C8H7N3O
3-(1-Methyl-5-imidazolyl)benzoic Acid 3-(1-Methyl-5-imidazolyl)benzoic Acid 1261269-06-0 C11H10N2O2
ethyl 1-benzyl-1H-iMidazole-2-carboxylate ethyl 1-benzyl-1H-iMidazole-2-carboxylate 865998-45-4 C13H14N2O2
4-Chloro-5-iodo-6-methylpyrimidin-2-amine 4-Chloro-5-iodo-6-methylpyrimidin-2-amine 897030-99-8 C5H5ClIN3
thieno[3,2-d]pyriMidine-7-carboxylic acid thieno[3,2-d]pyriMidine-7-carboxylic acid 1211596-20-1 C7H4N2O2S
1H-Benzo[d]imidazol-6-ylboronic acid 1H-Benzo[d]imidazol-6-ylboronic acid 1228183-22-9 C7H7BN2O2
2,3-Dichlorotetrahydrofuran 2,3-Dichlorotetrahydrofuran 3511-19-1 C4H6Cl2O
1H-Indole, 6-broMo-4-chloro- 1H-Indole, 6-broMo-4-chloro- 885519-01-7 C8H5BrClN
IMidazo[1,2-a]pyridine-2-carboxylic acid, 7-chloro-, ethyl ester IMidazo[1,2-a]pyridine-2-carboxylic acid, 7-chloro-, ethyl ester 1204501-38-1 C10H9ClN2O2
IMidazo[1,2-a]pyridine-6-carboxylic acid, 2-Methyl- IMidazo[1,2-a]pyridine-6-carboxylic acid, 2-Methyl- 129912-22-7 C9H8N2O2
(R)-1-acetyl-2-PyrrolidineMethanol (R)-1-acetyl-2-PyrrolidineMethanol 123958-87-2 C7H13NO2
3-d]pyriMidine-6-carboxylic acid 3-d]pyriMidine-6-carboxylic acid 873544-81-1 C7H5N3O3S
2-a]pyrazine 2-a]pyrazine 91775-61-0 C7H6BrN3O
3H-IMidazo[4,5-c]pyridine, 2-(2-fluorophenyl)- 3H-IMidazo[4,5-c]pyridine, 2-(2-fluorophenyl)- 89075-43-4 C12H8FN3
7-Chloropyrazolo[1,5-a]pyiMidine-3-carbonitrile 7-Chloropyrazolo[1,5-a]pyiMidine-3-carbonitrile 1159982-97-4 C7H3ClN4
4-ChloroMethyl-1H-pyrrolo[2,3-b]pyridine 4-ChloroMethyl-1H-pyrrolo[2,3-b]pyridine 1268390-67-5 C8H7ClN2
4,7-dibroMobenzo[1,2-c:4,5-c']bis([1,2,5]thiadiazole) 4,7-dibroMobenzo[1,2-c:4,5-c']bis([1,2,5]thiadiazole) 165617-59-4 C6Br2N4S2
5,6,7,8-tetrahydroiMidazo[1,2-a]pyridin-6-ol 5,6,7,8-tetrahydroiMidazo[1,2-a]pyridin-6-ol 1100750-16-0 C7H10N2O
5-broMo-2-(3-(chloroMethyl)phenyl)pyriMidine 5-broMo-2-(3-(chloroMethyl)phenyl)pyriMidine 1100598-50-2 C11H8BrClN2
4-MethylpyriMidine-2-carboxaMide 4-MethylpyriMidine-2-carboxaMide 1330754-32-9 C6H7N3O
L-Proline, N-[(1,1-diMethylethoxy)carbonyl]glycyl-4-(benzoylaMino)-, (4R)- L-Proline, N-[(1,1-diMethylethoxy)carbonyl]glycyl-4-(benzoylaMino)-, (4R)- 943134-34-7 C19H25N3O6
7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,2,4]triazolo[1,5-a]pyridine 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,2,4]triazolo[1,5-a]pyridine 1210048-18-2 C12H16BN3O2
7-BroMo-3-iodo-iMidazo[1,2-a]pyridine 7-BroMo-3-iodo-iMidazo[1,2-a]pyridine 1246184-55-3 C7H4BrIN2
5-(hydroxyMethyl)-1-Methylpyrrolidin-2-one 5-(hydroxyMethyl)-1-Methylpyrrolidin-2-one 89531-41-9 C6H11NO2
1-(3-Methyl-4-nitrophenyl)-1H-imidazole 1-(3-Methyl-4-nitrophenyl)-1H-imidazole 102791-92-4 C10H9N3O2
3-AMino-1-Boc-4,4-difluoropyrrolidine 3-AMino-1-Boc-4,4-difluoropyrrolidine 1408074-83-8 C9H16F2N2O2
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