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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
2-(6-amino-pyridin-3-yl)benzonitrile 2-(6-amino-pyridin-3-yl)benzonitrile 352615-86-2 C12H9N3
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-Methyl-1H-pyrrolo[2,3-c]pyridine 4-Methyl-1H-pyrrolo[2,3-c]pyridine 1190321-86-8 C8H8N2
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
3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile 3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile 479411-96-6 C13H15BBrNO2
Sunifiram Sunifiram 314728-85-3 C14H18N2O2
4-broMo-2-isopropylpyriMidine 4-broMo-2-isopropylpyriMidine 1060813-15-1 C7H9BrN2
2-(4-BroMo-3-Methyl-pyrazol-1-yl)-ethanol 2-(4-BroMo-3-Methyl-pyrazol-1-yl)-ethanol 1352503-76-4 C6H9BrN2O
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-broMopyriMidin-4-ol 2-broMopyriMidin-4-ol 1160994-75-1 C4H3BrN2O
2-a]pyrazine 2-a]pyrazine 91775-61-0 C7H6BrN3O
7,8-dihydro-5H-cyclohepta[b]pyridine-5,9(6H)-dione 7,8-dihydro-5H-cyclohepta[b]pyridine-5,9(6H)-dione 39713-40-1 C10H9NO2
3H-IMidazo[4,5-c]pyridine, 2-(2-fluorophenyl)- 3H-IMidazo[4,5-c]pyridine, 2-(2-fluorophenyl)- 89075-43-4 C12H8FN3
(1R,5S)-6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2,4-dione (1R,5S)-6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2,4-dione 194421-56-2 C7H9NO2
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
2-(4-BroMopyrazol-1-yl)benzonitrile 2-(4-BroMopyrazol-1-yl)benzonitrile 1184023-09-3 C10H6BrN3
4-Pyridinol, 2-cyclobutyl- 4-Pyridinol, 2-cyclobutyl- 1159814-25-1 C9H11NO
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
4-chloro-2-(2-(trifluoroMethyl)phenyl)pyriMidine 4-chloro-2-(2-(trifluoroMethyl)phenyl)pyriMidine 1155598-43-8 C11H6ClF3N2
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
1-(3-Methyl-1-phenyl-5-pyrazolyl)piperazine 1-(3-Methyl-1-phenyl-5-pyrazolyl)piperazine 401566-79-8 C14H18N4
5-broMo-2-(3-(chloroMethyl)phenyl)pyriMidine 5-broMo-2-(3-(chloroMethyl)phenyl)pyriMidine 1100598-50-2 C11H8BrClN2
2-(Furan-2-yl)pyriMidin-5-aMine 2-(Furan-2-yl)pyriMidin-5-aMine 27130-78-5 C8H7N3O
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
9-(1-Naphthyl) carbazole 9-(1-Naphthyl) carbazole 22034-43-1 C22H15N
1-(3-Methyl-4-nitrophenyl)-1H-imidazole 1-(3-Methyl-4-nitrophenyl)-1H-imidazole 102791-92-4 C10H9N3O2
1-METHYL-PIPERIDINE-4-CARBONITRILE 1-METHYL-PIPERIDINE-4-CARBONITRILE 20691-92-3 C7H12N2
5-iodo-1,4-diMethyl-1H-1,2,3-triazole 5-iodo-1,4-diMethyl-1H-1,2,3-triazole 1346818-62-9 C4H6IN3
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
4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2-p-tolylpyridine 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-2-p-tolylpyridine 1402172-12-6 C18H22BNO2
6-(pyridin-4-yl)pyridazin-3-aMine 6-(pyridin-4-yl)pyridazin-3-aMine 1159818-48-0 C9H8N4
4-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)benzonitrile 4-(4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)benzonitrile 1402166-72-6 C16H18BN3O2
6'-broMospiro[cyclopropane-1,3'-indoline] 6'-broMospiro[cyclopropane-1,3'-indoline] 1379360-39-0 C10H10BrN
4-Bromo-2-(2-methylpiperidin-1-yl)pyridine 4-Bromo-2-(2-methylpiperidin-1-yl)pyridine 1142194-41-9 C11H15BrN2
methyl 1-benzylpyrrolidine-3-carboxylate methyl 1-benzylpyrrolidine-3-carboxylate 126344-02-3 C13H17NO2
3-Pyridazinamine, 6-[2-(trifluoromethyl)phenyl]- 3-Pyridazinamine, 6-[2-(trifluoromethyl)phenyl]- 1215072-76-6 C11H8F3N3
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-ethenyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid 1-ethenyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid 340023-04-3 C10H14O3
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
6-(pyridin-2-yl)pyridazin-3-amine 6-(pyridin-2-yl)pyridazin-3-amine 1159817-09-0 C9H8N4
tert-Butyl 3-(2-bromoethyl)azetidine-1-carboxylate tert-Butyl 3-(2-bromoethyl)azetidine-1-carboxylate 1420859-80-8 C10H18BrNO2
3-(4-Fluorophenyl)-1H-1,2,4-triazole 3-(4-Fluorophenyl)-1H-1,2,4-triazole 95728-10-2 C8H6FN3
2-(bromo(phenyl)methyl)pyridine 2-(bromo(phenyl)methyl)pyridine 1073477-82-3 C12H10BrN
2-chloro-5-(pyridin-2-yl)pyrimidine 2-chloro-5-(pyridin-2-yl)pyrimidine 374927-80-7 C9H6ClN3
6-(3-aminophenyl)pyridazin-3(2{H})-one 6-(3-aminophenyl)pyridazin-3(2{H})-one 24912-36-5 C10H9N3O
tert-butyl 2-(4-bromophenyl)morpholine-4-carboxylate tert-butyl 2-(4-bromophenyl)morpholine-4-carboxylate 1131220-82-0 C15H20BrNO3
2,6-dibromo-3-cyclopropylPyridine 2,6-dibromo-3-cyclopropylPyridine 1430329-84-2 C8H7Br2N
5-(2-methylphenyl)-1H-1,2,3-Triazole 5-(2-methylphenyl)-1H-1,2,3-Triazole 369363-70-2 C9H9N3
4-phenyl-2-Thiophenamine 4-phenyl-2-Thiophenamine 67637-83-6 C10H9NS
6-(1-piperidinyl)-2-Pyridinamine 6-(1-piperidinyl)-2-Pyridinamine 4945-46-4 C10H15N3
2-bromo-4-(cyclopentyloxy)Pyridine 2-bromo-4-(cyclopentyloxy)Pyridine 1142194-85-1 C10H12BrNO
6-(cyclopentyloxy)-3-Pyridazinamine 6-(cyclopentyloxy)-3-Pyridazinamine 1177269-29-2 C9H13N3O
4-isopropoxypyridin-2-amine 4-isopropoxypyridin-2-amine 1314353-62-2 C8H12N2O
tert-butyl 7-amino-2-azaspiro[4.4]nonane-2-carboxylate tert-butyl 7-amino-2-azaspiro[4.4]nonane-2-carboxylate 1341037-08-8 C13H24N2O2
1-(3-Bromo-4-methylbenzyl)pyrrolidine 1-(3-Bromo-4-methylbenzyl)pyrrolidine 1414870-50-0 C12H16BrN
7-bromo-2,4,6-trichloro-8-fluoroquinazoline 7-bromo-2,4,6-trichloro-8-fluoroquinazoline 1698028-11-3 C8HBrCl3FN2
3-Bromo-6-pyridin-4-yl-pyridazine 3-Bromo-6-pyridin-4-yl-pyridazine 1159818-39-9 C9H6BrN3
5-Bromo-2-methylpyrazolo[1,5-a]pyrimidine 5-Bromo-2-methylpyrazolo[1,5-a]pyrimidine 1610021-32-3 C7H6BrN3
2-(3-pyridyl)thiazole-4-boronic acid pinacol ester 2-(3-pyridyl)thiazole-4-boronic acid pinacol ester 1402165-87-0 C14H17BN2O2S
1-Chloro-9H-carbazole 1-Chloro-9H-carbazole 5599-70-2 C12H8ClN
4-Bromo-5-methylpyridin-2(1H)-one 4-Bromo-5-methylpyridin-2(1H)-one 1227578-85-9 C6H6BrNO
4-BROMO-1-PHENYL-1H-PYRAZOLE 4-BROMO-1-PHENYL-1H-PYRAZOLE 15115-52-3 C9H7BrN2
2-(4-Bromo-1-pyrazolyl)ethyl Acetate 2-(4-Bromo-1-pyrazolyl)ethyl Acetate 1215073-99-6 C7H9BrN2O2
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
4-(2-Bromo-pyrimidin-4-yl)- piperidine-1-carboxylic acid tert-butyl ester 4-(2-Bromo-pyrimidin-4-yl)- piperidine-1-carboxylic acid tert-butyl ester 1398603-45-6 C14H20BrN3O2
6-Bromo-5-methoxy-3H-imidazo[4,5-b]pyridine 6-Bromo-5-methoxy-3H-imidazo[4,5-b]pyridine 2708194-57-2 C7H6BrN3O
N3,N3-Dimethylpyridine-2,3-diamine N3,N3-Dimethylpyridine-2,3-diamine 50426-30-7 C7H11N3
Phosphinic acid, di-4-morpholinyl-, butyl ester (9CI) Phosphinic acid, di-4-morpholinyl-, butyl ester (9CI) 5326-05-6 C12H25N2O4P
4(1H)-Pyrimidinone, 2-(4-methoxyphenyl)- 4(1H)-Pyrimidinone, 2-(4-methoxyphenyl)- 88627-13-8 C11H10N2O2
4-ETHYL-1,3-THIAZOL-5-AMINE 4-ETHYL-1,3-THIAZOL-5-AMINE 1249955-33-6 C5H8N2S
5-bromo-2-(4-methoxyphenyl)pyrimidine 5-bromo-2-(4-methoxyphenyl)pyrimidine 177727-12-7 C11H9BrN2O
N-ACETOACETYLMORPHOLINE N-ACETOACETYLMORPHOLINE 16695-54-8 C8H13NO3
2-chloro-4-phenylbenzo[h]quinazoline 2-chloro-4-phenylbenzo[h]quinazoline 4786-80-5 C18H11ClN2
4-Bromo-2-fluoro-5-(trifluoromethyl)pyridine 4-Bromo-2-fluoro-5-(trifluoromethyl)pyridine 1227600-03-4 C6H2BrF4N
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