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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
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
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
2,4-Diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine 2,4-Diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine 1219956-23-6 C27H26BN3O2
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
6-amino-1-((2S,4R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxypyrrolidin-1-yl)hexan-1-one 6-amino-1-((2S,4R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxypyrrolidin-1-yl)hexan-1-one
5H-indeno[1,2-b]pyridine 5H-indeno[1,2-b]pyridine 244-99-5 C12H9N
N,N-dimethylthio-2-thioxoimidazolidine-1-carboxamide N,N-dimethylthio-2-thioxoimidazolidine-1-carboxamide 935-75-1 C6H11N3OS3
2-(pyrrolidinyl)pyrimidin-4-amine 2-(pyrrolidinyl)pyrimidin-4-amine 33851-99-9 C8H12N4
2,5-Bis(octyldithio)-1,3,4-thiadiazole 2,5-Bis(octyldithio)-1,3,4-thiadiazole 13539-13-4 C18H34N2S5
4,5-dihydro-2-vinyl-1H-imidazole 4,5-dihydro-2-vinyl-1H-imidazole 10577-96-5 C5H8N2
4-(2,5-dibutoxy-4-nitrophenyl)morpholine 4-(2,5-dibutoxy-4-nitrophenyl)morpholine 86-15-7 C18H28N2O5
2,6-Pyridinedicarboxamide, N2,N6-bis[(diethylamino)thioxomethyl]- 2,6-Pyridinedicarboxamide, N2,N6-bis[(diethylamino)thioxomethyl]- 320408-75-1 C17H25N5O2S2
4,4,4',4',5,5,5',5'-octaethyl-2,2'-bi(1,3,2-dioxaborolane) 4,4,4',4',5,5,5',5'-octaethyl-2,2'-bi(1,3,2-dioxaborolane) 2247367-07-1 C20H40B2O4
L-Proline, 1-(2-naphthalenylacetyl)- (9CI) L-Proline, 1-(2-naphthalenylacetyl)- (9CI) 130654-11-4 C17H17NO3
3H-Imidazo[4,5-c]pyridine-3,5,6(4H)-tricarboxylic acid, 6,7-dihydro-, 3,5-bis(1,1-dimethylethyl) ester, (6S)- 3H-Imidazo[4,5-c]pyridine-3,5,6(4H)-tricarboxylic acid, 6,7-dihydro-, 3,5-bis(1,1-dimethylethyl) ester, (6S)- 1415602-89-9 C17H25N3O6
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
3'-Deoxyneamine 3'-Deoxyneamine 34051-04-2 C12H26N4O5
4-[[(1-propyl-1H-imidazol-5-yl)methyl]sulfinyl]Benzenamine 4-[[(1-propyl-1H-imidazol-5-yl)methyl]sulfinyl]Benzenamine 597583-07-8 C13H17N3OS
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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