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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
3,4-DICHLOROPICOLINIC ACID 3,4-DICHLOROPICOLINIC ACID 959578-03-1 C6H3Cl2NO2
5-BROMO-1,4-DIMETHYL-1H-1,2,3-TRIAZOLE 5-BROMO-1,4-DIMETHYL-1H-1,2,3-TRIAZOLE 1040275-55-5 C4H6BrN3
1-(3-BROMOPROPYL)PYRROLIDINE-2,5-DIONE 1-(3-BROMOPROPYL)PYRROLIDINE-2,5-DIONE 88661-56-7 C7H10BrNO2
Ethyl 5-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate Ethyl 5-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate 1260885-46-8 C11H9F3N2O2
4-isocyanato-1-methyl-1H-pyrazole 4-isocyanato-1-methyl-1H-pyrazole 1174064-57-3 C5H5N3O
2-Methoxy-4-(tributylstannyl)pyridine 2-Methoxy-4-(tributylstannyl)pyridine 1204580-72-2 C18H33NOSn
6-Chloropyrimido[5,4-d]pyrimidin-4(3H)-one 6-Chloropyrimido[5,4-d]pyrimidin-4(3H)-one 189747-31-7 C6H3ClN4O
JWH 412 JWH 412 1364933-59-4 C24H22FNO
ethyl 5-amino-1-(pyrimidin-2-yl)-1H-pyrazole-4-carboxylate ethyl 5-amino-1-(pyrimidin-2-yl)-1H-pyrazole-4-carboxylate 91129-95-2 C10H11N5O2
1-(2-fluorophenyl)-1H-pyrazol-4-amine 1-(2-fluorophenyl)-1H-pyrazol-4-amine 1153040-48-2 C9H8FN3
1-(3,4-difluorophenyl)-1H-pyrazol-4-amine 1-(3,4-difluorophenyl)-1H-pyrazol-4-amine 1233698-57-1 C9H7F2N3
1-p-tolyl-1H-pyrazol-4-amine 1-p-tolyl-1H-pyrazol-4-amine 90839-86-4 C10H11N3
3-bromo-1-(2-(trifluoromethyl)phenyl)-1H-pyrazole 3-bromo-1-(2-(trifluoromethyl)phenyl)-1H-pyrazole 2241865-52-9 C10H6BrF3N2
3-bromo-1-cyclohexyl-1H-pyrazole 3-bromo-1-cyclohexyl-1H-pyrazole 1427020-80-1 C9H13BrN2
4-bromo-1-(4-chlorophenyl)-1H-pyrazole 4-bromo-1-(4-chlorophenyl)-1H-pyrazole 885017-82-3 C9H6BrClN2
(S)-3-Methylmorpholine hydrochloride (S)-3-Methylmorpholine hydrochloride 1022094-03-6 C5H12ClNO
4-methoxycarbonyl-6,6'-dimethyl-2,2'-bipyridine 4-methoxycarbonyl-6,6'-dimethyl-2,2'-bipyridine 562086-30-0 C14H14N2O2
3-bromo-5-(3-methylphenyl)-1H-1,2,4-triazole(SALTDATA: FREE) 3-bromo-5-(3-methylphenyl)-1H-1,2,4-triazole(SALTDATA: FREE) 1227465-57-7 C9H8BrN3
7-CHLORO-5-METHYL-1H-PYRAZOLO[4,3-B]PYRIDINE 7-CHLORO-5-METHYL-1H-PYRAZOLO[4,3-B]PYRIDINE 94220-38-9 C7H6ClN3
7-(chloromethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one(SALTDATA: FREE) 7-(chloromethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one(SALTDATA: FREE) 87572-02-9 C6H4ClN3OS
3-PHENYLPHTHALIDE 3-PHENYLPHTHALIDE 5398-11-8 C14H10O2
2-broMo-5-(piperidin-3-yl)pyridine 2-broMo-5-(piperidin-3-yl)pyridine 1260873-88-8 C10H13BrN2
3-broMo-5-(piperidin-4-yl)pyridine 3-broMo-5-(piperidin-4-yl)pyridine 899356-77-5 C10H13BrN2
4-broMo-2-(pyrrolidin-3-yl)pyridine 4-broMo-2-(pyrrolidin-3-yl)pyridine 1260641-94-8 C9H11BrN2
2-(azetidin-1-yl)-6-broMopyridine 2-(azetidin-1-yl)-6-broMopyridine 1288991-76-3 C8H9BrN2
3-Iodo-2-methoxy-6-(pyrrolidin-1-yl)pyridine 3-Iodo-2-methoxy-6-(pyrrolidin-1-yl)pyridine 1228666-06-5 C10H13IN2O
ethyl 5-oxo-5H-thiazolo[3,2-a]pyriMidine-6-carboxylate ethyl 5-oxo-5H-thiazolo[3,2-a]pyriMidine-6-carboxylate 32278-52-7 C9H8N2O3S
1H-Pyrrolo[2,3-b]pyridine, 5-(4-chlorophenyl)- 1H-Pyrrolo[2,3-b]pyridine, 5-(4-chlorophenyl)- 918516-27-5 C13H9ClN2
N-(2-Methoxyethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine N-(2-Methoxyethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine 1202805-24-0 C13H22BN3O3
1,3-diMethyliMidazoliuM bis((trifluoroMethyl)sulfonyl)iMide 1,3-diMethyliMidazoliuM bis((trifluoroMethyl)sulfonyl)iMide 174899-81-1 C7H9F6N3O4S2
1-propenyl-3-MethyliMidazoliuM nitrate 1-propenyl-3-MethyliMidazoliuM nitrate 649745-76-6 C7H11N3O3
N-Dodecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate N-Dodecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate 14933-08-5 C17H37NO3S
1-tert-butyl-1H-pyrazole-4-carbonitrile 1-tert-butyl-1H-pyrazole-4-carbonitrile 149139-43-5 C8H11N3
tert-Butyl (3S,4R)-4(3-Fluorophenyl)pyrrolidin-3-ylcarbaMate tert-Butyl (3S,4R)-4(3-Fluorophenyl)pyrrolidin-3-ylcarbaMate 1260596-09-5 C15H21FN2O2
2-broMo-4-isopropylthiazole 2-broMo-4-isopropylthiazole 1026598-63-9 C6H8BrNS
1-(4-broMo-2-fluorophenyl)-4-Methyl-1H-iMidazole 1-(4-broMo-2-fluorophenyl)-4-Methyl-1H-iMidazole 1241675-16-0 C10H8BrFN2
N-[3-(1-IMidazolyl)propyl]-2,4-dichlorobenzaMide N-[3-(1-IMidazolyl)propyl]-2,4-dichlorobenzaMide 349092-52-0 C13H13Cl2N3O
IMidazo[1,2-a]pyridine, 8-broMo-6-fluoro- IMidazo[1,2-a]pyridine, 8-broMo-6-fluoro- 1368664-08-7 C7H4BrFN2
IMidazo[1,2-a]pyridine-2-carboxylic acid, 7-Methoxy- IMidazo[1,2-a]pyridine-2-carboxylic acid, 7-Methoxy- 129912-15-8 C9H8N2O3
1H-IMidazole-2-carboxylic acid, 4-[[(1,1-diMethylethoxy)carbonyl]aMino]-1-Methyl-, ethyl ester 1H-IMidazole-2-carboxylic acid, 4-[[(1,1-diMethylethoxy)carbonyl]aMino]-1-Methyl-, ethyl ester 128293-63-0 C12H19N3O4
4-chloro-2-(trifluoroMethyl)-1H-pyrrolo[2,3-b]pyridine 4-chloro-2-(trifluoroMethyl)-1H-pyrrolo[2,3-b]pyridine 1014613-16-1 C8H4ClF3N2
(R)-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole (R)-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole 143322-55-8 C14H18N2
benzyl 2-(5-broMo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate benzyl 2-(5-broMo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate 331842-86-5 C21H19BrN2O3
4-chloro-1-(4-Methoxybenzyl)-1H-iMidazo[4,5-c]pyridine 4-chloro-1-(4-Methoxybenzyl)-1H-iMidazo[4,5-c]pyridine 881844-11-7 C14H12ClN3O
1-(3-Methoxypropyl)-4-oxo-1,4-dihydropyrido[1,2-a]pyrrolo[2,3-d]pyriMidine-2-carboxylic acid 1-(3-Methoxypropyl)-4-oxo-1,4-dihydropyrido[1,2-a]pyrrolo[2,3-d]pyriMidine-2-carboxylic acid 1086386-77-7 C15H15N3O4
2-broMo-6-cyclobutylpyridine 2-broMo-6-cyclobutylpyridine 1086381-53-4 C9H10BrN
2-(Chloromethyl)-5-pyrimidinecarbonitrile 2-(Chloromethyl)-5-pyrimidinecarbonitrile 1086393-94-3 C6H4ClN3
IMidazo[1,5-a]pyrazine, 5,6,7,8-tetrahydro-1,3-diMethyl- IMidazo[1,5-a]pyrazine, 5,6,7,8-tetrahydro-1,3-diMethyl- 1083317-78-5 C8H13N3
4-Chloro-2-cyclopropyl-6-phenylpyriMidine 4-Chloro-2-cyclopropyl-6-phenylpyriMidine 1153412-53-3 C13H11ClN2
1,3,2-Dioxathiolane, 4-Methyl-, 2,2-dioxide, (4R)- 1,3,2-Dioxathiolane, 4-Methyl-, 2,2-dioxide, (4R)- 1006381-03-8 C3H6O4S
1H-BenziMidazole, 6-(2-chloro-5-fluoro-4-pyriMidinyl)-4-fluoro-2-Methyl-1-(1-Methylethyl)- 1H-BenziMidazole, 6-(2-chloro-5-fluoro-4-pyriMidinyl)-4-fluoro-2-Methyl-1-(1-Methylethyl)- 1231930-42-9 C15H13ClF2N4
1H-IMidazole, 4-broMo-1-Methyl-2-(2-Methylphenyl)- 1H-IMidazole, 4-broMo-1-Methyl-2-(2-Methylphenyl)- 1049126-60-4 C11H11BrN2
1,2-Pyrrolidinedicarboxylic acid, 4-(benzoylaMino)-, 1-(1,1-diMethylethyl) 2-Methyl ester, (2S,4R)- 1,2-Pyrrolidinedicarboxylic acid, 4-(benzoylaMino)-, 1-(1,1-diMethylethyl) 2-Methyl ester, (2S,4R)- 943134-37-0 C18H24N2O5
6-broMo-3-chloroiMidazo[1,2-a]pyriMidine 6-broMo-3-chloroiMidazo[1,2-a]pyriMidine 1019025-49-0 C6H3BrClN3
(R)-3-Methylpyrrolidine-3-carboxylic acid (R)-3-Methylpyrrolidine-3-carboxylic acid 1410783-77-5 C6H11NO2
5-AMINO-4-CYANO-3-CYANOMETHYLPYRAZOLE 5-AMINO-4-CYANO-3-CYANOMETHYLPYRAZOLE 54711-21-6 C6H5N5
2-(2-BroMo-pyridin-4-yl)-propan-2-ol 2-(2-BroMo-pyridin-4-yl)-propan-2-ol 1055073-69-2 C8H10BrNO
(1S,3S)-phenylethylpyrrolidinylMethanol (1S,3S)-phenylethylpyrrolidinylMethanol 173724-95-3 C13H19NO
6-benzyl-2,4-dichloro-8,8-difluoro-5,6,7,8-tetrahydropyrido[4,3-d]pyriMidine HYDROCHLORIDE 6-benzyl-2,4-dichloro-8,8-difluoro-5,6,7,8-tetrahydropyrido[4,3-d]pyriMidine HYDROCHLORIDE 1864059-82-4 C14H12Cl3F2N3
4-Thien-2-ylpyridin-2-amine 4-Thien-2-ylpyridin-2-amine 1159815-95-8 C9H8N2S
2-(Oxetan-3-yloxy)pyridin-3-amine 2-(Oxetan-3-yloxy)pyridin-3-amine 1349718-81-5 C8H10N2O2
(5S)-5-Methyl-2-Pyrrolidinone (5S)-5-Methyl-2-Pyrrolidinone 1558-60-7 C5H9NO
(3S,5S)-5-Methylpyrrolidin-3-ol (3S,5S)-5-Methylpyrrolidin-3-ol 1108234-24-7 C5H11NO
IMidazo[1,2-d][1,4]benzoxazepine, 9-broMo-5,6-dihydro-2-[3-Methyl-1-(1-Methylethyl)-1H-1,2,4-triazol-5-yl]- IMidazo[1,2-d][1,4]benzoxazepine, 9-broMo-5,6-dihydro-2-[3-Methyl-1-(1-Methylethyl)-1H-1,2,4-triazol-5-yl]- 1282514-63-9 C17H18BrN5O
2-(2-Methylpiperidin-1-yl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(2-Methylpiperidin-1-yl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine 1350748-06-9 C17H27BN2O2
6-(4-aMinophenyl)pyridazin-3-aMine 6-(4-aMinophenyl)pyridazin-3-aMine 1215073-63-4 C10H10N4
2-piperidino-4-chloropyrimidine 2-piperidino-4-chloropyrimidine 24192-95-8 C9H12ClN3
4-BroMo-5-chloro-1H-indazole 4-BroMo-5-chloro-1H-indazole 1056264-74-4 C7H4BrClN2
5-(pyrrolidin-3-yl)-2-(trifluoromethyl)pyridine 5-(pyrrolidin-3-yl)-2-(trifluoromethyl)pyridine 1234482-76-8 C10H11F3N2
(S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile 2,2,2-trifluoroacetate (S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile 2,2,2-trifluoroacetate 1448440-40-1 C9H10F5N3O3
2-Pyrrolidinecarboxamide, N-(4-phenyl-1,2,3-thiadiazol-5-yl)-, monohydrochloride, (2S)- (9CI) 2-Pyrrolidinecarboxamide, N-(4-phenyl-1,2,3-thiadiazol-5-yl)-, monohydrochloride, (2S)- (9CI) 873581-19-2 C13H15ClN4OS
7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2,4-diol 7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2,4-diol 1478126-83-8 C7H8N2O3
3-Oxazolidinecarboxylic acid, 4-methyl-2,5-dioxo-, 1,1-dimethylethyl ester, (4R)- 3-Oxazolidinecarboxylic acid, 4-methyl-2,5-dioxo-, 1,1-dimethylethyl ester, (4R)- 161422-40-8 C9H13NO5
(1H-Imidazol-2-yl)-hydrazine hydrochloride (1H-Imidazol-2-yl)-hydrazine hydrochloride 1187929-07-2 C3H7ClN4
2-Oxa-6-azaspiro[3.4]octane hemioxalate 2-Oxa-6-azaspiro[3.4]octane hemioxalate 1523570-96-8 C8H13NO5
P4S10-Pyridine complex P4S10-Pyridine complex 16610-51-8 C10H10N2P2S5
1,1'-Thiocarbonyldiimidazole 1,1'-Thiocarbonyldiimidazole 6160-65-2 C7H6N4S
(R)-5-Hydroxymethyldihydrofuran-2-one (R)-5-Hydroxymethyldihydrofuran-2-one 52813-63-5 C5H8O3
(2R,3R)-2-PHENYL-PYRROLIDINE-3-CARBOXYLIC ACID (2R,3R)-2-PHENYL-PYRROLIDINE-3-CARBOXYLIC ACID 1241684-18-3 C11H13NO2
(R)-3-Methylpiperazin-2-one (R)-3-Methylpiperazin-2-one 922178-61-8 C5H10N2O
3-CYCLOHEXYL-PYRROLIDINE 3-CYCLOHEXYL-PYRROLIDINE 78813-85-1 C10H19N
Vinyl pyridine Vinyl pyridine C7H7N
tert-butyl 1,6-diazaspiro[3.3]heptane-1-carboxylate hemioxalate tert-butyl 1,6-diazaspiro[3.3]heptane-1-carboxylate hemioxalate 1523571-10-9 C22H38N4O8
1-Piperidinecarboxylic acid, 4-(4-pyrimidinyl)-, 1,1-dimethylethyl ester 1-Piperidinecarboxylic acid, 4-(4-pyrimidinyl)-, 1,1-dimethylethyl ester 1266114-58-2 C14H21N3O2
2-chloro-5-isopropylpyridin-4-amine 2-chloro-5-isopropylpyridin-4-amine 1381935-97-2 C8H11ClN2
2-Morpholinoethanol 2-Morpholinoethanol 622-40-2 C6H13NO2
5-(m-Tolyl)-1H-1,2,3-triazole 5-(m-Tolyl)-1H-1,2,3-triazole 55862-00-5 C9H9N3
3-bromo-5-isopropylpyridin-2-amine 3-bromo-5-isopropylpyridin-2-amine 1381938-44-8 C8H11BrN2
8-Ethyl-2-methanethio-8H-pyrido[2,3-d]pyrimidin-7-one 8-Ethyl-2-methanethio-8H-pyrido[2,3-d]pyrimidin-7-one 211244-82-5 C10H11N3OS
2-(Furan-2-yl)propan-2-ol 2-(Furan-2-yl)propan-2-ol 6378-58-1 C7H10O2
3-Bromo-6-(pyridin-3-yl)pyridazine 3-Bromo-6-(pyridin-3-yl)pyridazine 1159818-53-7 C9H6BrN3
4-(4-methylpiperazin-1-yl)pyridin-2-amine 4-(4-methylpiperazin-1-yl)pyridin-2-amine 959986-12-0 C10H16N4
Octanoic acid, 8-oxo-8-(3-pyridinylamino)-, methyl ester
Octanoic acid, 8-oxo-8-(3-pyridinylamino)-, methyl ester 405096-07-3 C14H20N2O3
2-isopropoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-isopropoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 1401350-37-5 C14H22BNO3
6-(4-methylpiperazin-1-yl)pyridin-2-amine 6-(4-methylpiperazin-1-yl)pyridin-2-amine 54132-20-6 C10H16N4
2-chloro-4-(thiophen-2-yl)-1,3,5-triazine 2-chloro-4-(thiophen-2-yl)-1,3,5-triazine 333737-07-8 C7H4ClN3S
5-(3-bromophenyl)-1H-1,2,3-Triazole 5-(3-bromophenyl)-1H-1,2,3-Triazole 35225-02-6 C8H6BrN3
2-bromo-6-cyclopentylPyridine 2-bromo-6-cyclopentylPyridine 463335-11-7 C10H12BrN
5-bromo-2-(2-methylthiazol-4-yl)pyridine 5-bromo-2-(2-methylthiazol-4-yl)pyridine 1159820-36-6 C9H7BrN2S
methyl 5-methoxy-3H-benzo[d]imidazole-4-carboxylate methyl 5-methoxy-3H-benzo[d]imidazole-4-carboxylate 1193789-02-4 C10H10N2O3
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