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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
MFCD00222735 MFCD00222735 3920-42-1 C5H7N3O2
{N-[3-(n6-phenyl)propyl]-[(1R-2R)-1,2-diphenyl-1-4-MethylbenzenesulfonylaMidato(kN')-ethyl-2-aMino-(kN)]}rutheniuM(II)  (R,R)-Teth-TsDpen RuCl WILLS CATALYST {N-[3-(n6-phenyl)propyl]-[(1R-2R)-1,2-diphenyl-1-4-MethylbenzenesulfonylaMidato(kN')-ethyl-2-aMino-(kN)]}rutheniuM(II) (R,R)-Teth-TsDpen RuCl WILLS CATALYST 1192620-83-9 C30H25ClN2O2RuS
methyl 1-benzylpyrrolidine-3-carboxylate methyl 1-benzylpyrrolidine-3-carboxylate 126344-02-3 C13H17NO2
3,4-Diiodo-5-methyl-1H-pyrazole 3,4-Diiodo-5-methyl-1H-pyrazole 6715-87-3 C4H4I2N2
2,4-dichlorobenzofuro[3,2-d]pyrimidine 2,4-dichlorobenzofuro[3,2-d]pyrimidine 160199-95-1 C10H4Cl2N2O
2-Acetyl-pyrrolidine hydrochloride 2-Acetyl-pyrrolidine hydrochloride 1956365-22-2 C6H12ClNO
5-Pyrimidinecarbonitrile, 2,4-diamino-6-chloro- 5-Pyrimidinecarbonitrile, 2,4-diamino-6-chloro- 900456-21-5 C5H4ClN5
1-(Propyltrimethoxyl)-3-methylimidazolium chloride 1-(Propyltrimethoxyl)-3-methylimidazolium chloride 856925-70-7 C10H19ClN2O3
(1-Methyl-1H-pyrazol-5-yl)tributylstannane (1-Methyl-1H-pyrazol-5-yl)tributylstannane 170682-50-5 C16H32N2Sn
3-(Bromomethyl)-5-methylisoxazole 3-(Bromomethyl)-5-methylisoxazole 130628-75-0 C5H6BrNO
2-(2-Chloroethyl)-1-methyl-1H-imidazole hydrochloride 2-(2-Chloroethyl)-1-methyl-1H-imidazole hydrochloride 1390654-72-4 C6H10Cl2N2
2-Methyl-4-isothiazolin-3-one hydrochloride 2-Methyl-4-isothiazolin-3-one hydrochloride 26172-54-3 C4H6ClNOS
1-tert-butyl 2-methyl (2S)-3,3-dimethyl-4-oxopyrrolidine-1,2-dicarboxylate 1-tert-butyl 2-methyl (2S)-3,3-dimethyl-4-oxopyrrolidine-1,2-dicarboxylate 478698-30-5 C13H21NO5
4-bromo-1H,2H,3H-pyrrolo[2,3-b]pyridine 4-bromo-1H,2H,3H-pyrrolo[2,3-b]pyridine 1393534-35-4 C7H7BrN2
2-(bromo(phenyl)methyl)pyridine 2-(bromo(phenyl)methyl)pyridine 1073477-82-3 C12H10BrN
1-(3-Bromo-4-methylbenzyl)pyrrolidine 1-(3-Bromo-4-methylbenzyl)pyrrolidine 1414870-50-0 C12H16BrN
5-Bromo-2-methylpyrazolo[1,5-a]pyrimidine 5-Bromo-2-methylpyrazolo[1,5-a]pyrimidine 1610021-32-3 C7H6BrN3
1-Chloro-9H-carbazole 1-Chloro-9H-carbazole 5599-70-2 C12H8ClN
4-BROMO-1-PHENYL-1H-PYRAZOLE 4-BROMO-1-PHENYL-1H-PYRAZOLE 15115-52-3 C9H7BrN2
2-ethyl-2,3-dihydro-2-(1H-imidazol-5-yl)-1H-Inden-1-one 2-ethyl-2,3-dihydro-2-(1H-imidazol-5-yl)-1H-Inden-1-one 104054-82-2 C14H14N2O
6-Bromo-5-methoxy-3H-imidazo[4,5-b]pyridine 6-Bromo-5-methoxy-3H-imidazo[4,5-b]pyridine 2708194-57-2 C7H6BrN3O
Phosphinic acid, di-4-morpholinyl-, butyl ester (9CI) Phosphinic acid, di-4-morpholinyl-, butyl ester (9CI) 5326-05-6 C12H25N2O4P
N-ACETOACETYLMORPHOLINE N-ACETOACETYLMORPHOLINE 16695-54-8 C8H13NO3
2-chloro-4-phenylbenzo[h]quinazoline 2-chloro-4-phenylbenzo[h]quinazoline 4786-80-5 C18H11ClN2
Alkyne NHS ester (hexynoic acid NHS ester) Alkyne NHS ester (hexynoic acid NHS ester) 906564-59-8 C10H11NO4
Benzo[b]naphtho[2,3-d]furan, 3-bromo- Benzo[b]naphtho[2,3-d]furan, 3-bromo- 1256544-32-7 C16H9BrO
1-Ethyl-3-methylimidazolium Tricyanomethanide 1-Ethyl-3-methylimidazolium Tricyanomethanide 666823-18-3 C10H11N5
4,4',4'',4'''-(2,2',4,4',6,6'-hexamethyl-[1,1'-biphenyl]-3,3',5,5'-tetrayl)tetrapyridine 4,4',4'',4'''-(2,2',4,4',6,6'-hexamethyl-[1,1'-biphenyl]-3,3',5,5'-tetrayl)tetrapyridine 809274-33-7 C38H34N4
5-(bromomethyl)-1-methyl-4-nitro-1H-imidazole 5-(bromomethyl)-1-methyl-4-nitro-1H-imidazole 1017279-02-5 C5H6BrN3O2
6-CHLOROIMIDAZO[2,1-B]THIAZOLE 6-CHLOROIMIDAZO[2,1-B]THIAZOLE 23576-81-0 C5H3ClN2S
2-AMINO-4-BROMOTHIAZOLE 2-AMINO-4-BROMOTHIAZOLE 502145-18-8 C3H3BrN2S
4-Chloroquinazoline 4-Chloroquinazoline 5190-68-1 C8H5ClN2
7-CHLOROPYRIDO[3,2-D]PYRIMIDIN-4(3H)-ONE 7-CHLOROPYRIDO[3,2-D]PYRIMIDIN-4(3H)-ONE 897360-16-6 C7H4ClN3O
(S)-(+)-2-(AMINOMETHYL)PYRROLIDINE (S)-(+)-2-(AMINOMETHYL)PYRROLIDINE 69500-64-7 C5H12N2
2,5-dioxopyrrolidin-1-yl 5-{2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl}pentanoate 2,5-dioxopyrrolidin-1-yl 5-{2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl}pentanoate 85718-04-3 C14H19N3O5S
2-(4,5-dimethyl-2-thienyl)pyrrolidine 2-(4,5-dimethyl-2-thienyl)pyrrolidine 1018163-24-0 C10H15NS
2-(4-TRIFLUOROMETHOXY-PHENYL)-PYRROLIDINE, HYDROCHLORIDE 2-(4-TRIFLUOROMETHOXY-PHENYL)-PYRROLIDINE, HYDROCHLORIDE 1185121-45-2 C11H13ClF3NO
2-(4-CHLOROBENZYLTHIO)-1H-BENZO[D]IMIDAZOLE 2-(4-CHLOROBENZYLTHIO)-1H-BENZO[D]IMIDAZOLE 23976-76-3 C14H11ClN2S
1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE 1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE 85909-08-6 C9H15NO3
Vanoxerine dihydrochloride Vanoxerine dihydrochloride 67469-78-7 C28H33ClF2N2O
1-(TRIMETHYLSILYL)-1H-BENZOTRIAZOLE 1-(TRIMETHYLSILYL)-1H-BENZOTRIAZOLE 43183-36-4 C9H13N3Si
5-(PYRIMIDIN-2-YLSULFANYL)-FURAN-2-CARBALDEHYDE 5-(PYRIMIDIN-2-YLSULFANYL)-FURAN-2-CARBALDEHYDE 57603-82-4 C9H6N2O2S
2-[4-(5-BROMOPYRIMIDIN-2-YL)PIPERAZIN-1-YL]ETHANOL 2-[4-(5-BROMOPYRIMIDIN-2-YL)PIPERAZIN-1-YL]ETHANOL 849021-42-7 C10H15BrN4O
2,6-bis[(4R,5R)-4,5-dihydro-4,5-diphenyl-1H-imidazol-2-yl]-Pyridine 2,6-bis[(4R,5R)-4,5-dihydro-4,5-diphenyl-1H-imidazol-2-yl]-Pyridine 863491-46-7 C35H29N5
3-AMINO-5-(METHYLTHIO)PYRAZOLE-4-CARBONITRILE 3-AMINO-5-(METHYLTHIO)PYRAZOLE-4-CARBONITRILE 72760-85-1 C5H6N4S
4-(PYRIMIDIN-2-YL)BROMOBENZENE 4-(PYRIMIDIN-2-YL)BROMOBENZENE 210354-17-9 C10H7BrN2
8-METHYL-2-PHENYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXALDEHYDE 8-METHYL-2-PHENYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXALDEHYDE 524724-72-9 C15H12N2O
(S)-ALPHA-(4-IODO-BENZYL)-PROLINE-HCL (S)-ALPHA-(4-IODO-BENZYL)-PROLINE-HCL 1217613-78-9 C12H15ClINO2
4-(4-Nitrophenoxy)aniline 4-(4-Nitrophenoxy)aniline 6149-33-3 C12H10N2O3
(S)-1-Boc-3-methylpiperazine (S)-1-Boc-3-methylpiperazine 147081-29-6 C10H20N2O2
4-Iodo-1H-imidazole-2-carboxylic acid 4-Iodo-1H-imidazole-2-carboxylic acid 1824286-45-4 C4H3IN2O2
imidazo[2,1-b][1,3]thiazol-3-ylmethanol imidazo[2,1-b][1,3]thiazol-3-ylmethanol 130182-36-4 C6H6N2OS
8-Bromo-5-fluoro-2,2-dimethyl-benzo[1,3]dioxin-4-one 8-Bromo-5-fluoro-2,2-dimethyl-benzo[1,3]dioxin-4-one 2006317-76-4 C10H8BrFO3
4-[[(1-propyl-1H-imidazol-5-yl)methyl]sulfinyl]Benzenamine 4-[[(1-propyl-1H-imidazol-5-yl)methyl]sulfinyl]Benzenamine 597583-07-8 C13H17N3OS
6-Bromoquinazoline 6-Bromoquinazoline 89892-21-7 C8H5BrN2
2-bromo-3H-imidazo[4,5-c]pyridine 2-bromo-3H-imidazo[4,5-c]pyridine 1557344-85-0 C6H4BrN3
5-(Aminomethyl)-5-(4-fluorophenyl)imidazolidine-2,4-dione hydrochloride 5-(Aminomethyl)-5-(4-fluorophenyl)imidazolidine-2,4-dione hydrochloride 1224885-25-9 C10H11ClFN3O2
 4-chloro-7-fluoro-quinazoline 4-chloro-7-fluoro-quinazoline 16499-62-0 C8H4ClFN2
3-(Benzo[d][1,3]dioxol-5-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 3-(Benzo[d][1,3]dioxol-5-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 61962-84-3 C13H9N3O3
6'-bromo-8'-chloro-1'H-spiro[cyclobutane-1,3'-imidazo[1,5-a]pyridine]-1',5'(2'H)-dione 6'-bromo-8'-chloro-1'H-spiro[cyclobutane-1,3'-imidazo[1,5-a]pyridine]-1',5'(2'H)-dione 1849592-10-4 C10H8BrClN2O2
7-Methyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid 7-Methyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid 874830-65-6 C10H7F3N2O2
Thieno[2,3-d]pyrimidine-6-carbaldehyde Thieno[2,3-d]pyrimidine-6-carbaldehyde 655253-72-8 C7H4N2OS
Benzyl [(1R,2R)-1-Hydroxy-1-phenyl-3-(1-pyrrolidinyl)-2-propanyl]carbamate Benzyl [(1R,2R)-1-Hydroxy-1-phenyl-3-(1-pyrrolidinyl)-2-propanyl]carbamate 193545-67-4 C21H26N2O3
4-BROMO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE 4-BROMO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE 497832-99-2 C5H4BrF3N2
Imidazo[1,2-a]pyrimidine Imidazo[1,2-a]pyrimidine 274-95-3 C6H5N3
2-ETHYL-4,4-DIMETHYL-2-OXAZOLINE 2-ETHYL-4,4-DIMETHYL-2-OXAZOLINE 5146-88-3 C7H13NO
1-(4-FLUOROPHENYL)IMIDAZOLINE-2-THIONE 1-(4-FLUOROPHENYL)IMIDAZOLINE-2-THIONE 17452-07-2 C9H7FN2S
3-methyl-1H-1,2,4-triazole-5-thiol 3-methyl-1H-1,2,4-triazole-5-thiol 7271-44-5 C3H5N3S
4-CHLORO-2-METHYLTHIOPYRAZOLO[1,5-A]1,3,5-TRIAZINE 4-CHLORO-2-METHYLTHIOPYRAZOLO[1,5-A]1,3,5-TRIAZINE 54346-19-9 C6H5ClN4S
L-CIS-PYRROLIDINE-2,4-DICARBOXYLIC ACID L-CIS-PYRROLIDINE-2,4-DICARBOXYLIC ACID 64927-38-4 C6H9NO4
RPA 202248 RPA 202248 143701-75-1 C15H12F3NO4S
1-Bromo-7-chlorodibenzo[b,d]furan 1-Bromo-7-chlorodibenzo[b,d]furan 2173555-52-5 C12H6BrClO
8-bromo-5-methyl-[1,2,4]triazolo[4,3-a]pyridine 8-bromo-5-methyl-[1,2,4]triazolo[4,3-a]pyridine 1379355-21-1 C7H6BrN3
(1R,2S,3S)-2-ethoxymethyl-3-(3,4-dichlorophenyl)-tropane (1R,2S,3S)-2-ethoxymethyl-3-(3,4-dichlorophenyl)-tropane
10-chloronaphtho[2,1-b]benzofuran 10-chloronaphtho[2,1-b]benzofuran 2140822-95-1 C16H9ClO
3-bromo-7-chlorodibenzo[b,d]furan 3-bromo-7-chlorodibenzo[b,d]furan 2244910-28-7 C12H6BrClO
1-((1H-pyrazol-1-yl)methyl)-1H-pyrazole 1-((1H-pyrazol-1-yl)methyl)-1H-pyrazole 27258-04-4 C7H8N4
6-(Tert-butylsulfonyl)-3-iodo-7-methoxyimidazo[1,2-a]pyridine 6-(Tert-butylsulfonyl)-3-iodo-7-methoxyimidazo[1,2-a]pyridine 2141961-59-1 C12H15IN2O3S
7-Bromo-4H-pyrazino[1,2-a]pyrimidin-4-one 7-Bromo-4H-pyrazino[1,2-a]pyrimidin-4-one 1848244-17-6 C7H4BrN3O
6-(2,2,2-Trifluoroethyl)thieno[3,2-d]pyrimidin-4(3H)-one 6-(2,2,2-Trifluoroethyl)thieno[3,2-d]pyrimidin-4(3H)-one 2163771-86-4 C8H5F3N2OS
1-tert-Butyl 3-methyl 3-(methylthio)pyrrolidine-1,3-dicarboxylate 1-tert-Butyl 3-methyl 3-(methylthio)pyrrolidine-1,3-dicarboxylate 942190-28-5 C12H21NO4S
(1-(pyrrolidin-1-ylmethyl)cyclopropyl)methanol (1-(pyrrolidin-1-ylmethyl)cyclopropyl)methanol 1174666-14-8 C9H17NO
3-Iodo-1H-indazole 3-Iodo-1H-indazole 66607-27-0 C7H5IN2
4-Formylmorpholine 4-Formylmorpholine 4394-85-8 C5H9NO2
2-PIPERIDIN-2-YL-1H-BENZOIMIDAZOLE 2-PIPERIDIN-2-YL-1H-BENZOIMIDAZOLE 51785-23-0 C12H15N3
2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine 2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine 128249-70-7 C23H19N3O2
4-Methoxy-2-indolinone 4-Methoxy-2-indolinone 7699-17-4 C9H9NO2
5-(pyrimidin-5-yl)isophthalic acid 5-(pyrimidin-5-yl)isophthalic acid 1417570-15-0 C12H8N2O4
5-chloro-3H-imidazo[4,5-b]pyridine-2-thiol 5-chloro-3H-imidazo[4,5-b]pyridine-2-thiol 40851-97-6 C6H4ClN3S
BIS(2-FURYL)CHLOROPHOSPHINE BIS(2-FURYL)CHLOROPHOSPHINE 181257-35-2 C8H6ClO2P
6-isopropylquinazoline 6-isopropylquinazoline 1059158-62-1 C11H12N2
(2S,4S)-1-(tert-Butoxycarbonyl)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidine-2-carboxylic acid (2S,4S)-1-(tert-Butoxycarbonyl)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidine-2-carboxylic acid 1821705-03-6 C24H33N5O4
(2S,5S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-5-phenylpyrrolidine-2-carboxylic acid (2S,5S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-5-phenylpyrrolidine-2-carboxylic acid 1219953-60-2 C26H23NO4
(2S)-3-(decyloxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid (2S)-3-(decyloxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid 1013997-51-7 C22H23NO4
(R)-4-Oxopyrrolidine-2-carboxylic acid (R)-4-Oxopyrrolidine-2-carboxylic acid 911284-93-0 C5H7NO3
Pyridine, 2,5-bis(2,3-difluorophenyl)- Pyridine, 2,5-bis(2,3-difluorophenyl)- 1261483-09-3 C17H9F4N
2,4(1H,3H)-Pyrimidinedione, 1-(4-bromophenyl)dihydro- 2,4(1H,3H)-Pyrimidinedione, 1-(4-bromophenyl)dihydro- 90772-28-4 C10H9BrN2O2
4-chloro-6-methyl-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine 4-chloro-6-methyl-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine 1258650-41-7 C8H10ClN3
Thiazolo[5,4-d]pyrimidin-5-amine, 7-chloro- Thiazolo[5,4-d]pyrimidin-5-amine, 7-chloro- 1211527-74-0 C5H3ClN4S
6-Bromo-1H-indole 6-Bromo-1H-indole 52415-29-9 C8H6BrN
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