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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
4-Chloro-3-(2-aminophenyl)pyridine 4-Chloro-3-(2-aminophenyl)pyridine 1563530-12-0 C11H9ClN2
4-Chloro-5-bromo-2-(2-methylimidazol-1-yl)pyrimidine 4-Chloro-5-bromo-2-(2-methylimidazol-1-yl)pyrimidine 1399482-65-5 C8H6BrClN4
4-Chloro-5-bromo-2-(3-chlorophenyl)pyrimidine 4-Chloro-5-bromo-2-(3-chlorophenyl)pyrimidine 1399481-70-9 C10H5BrCl2N2
4-Chloro-5-bromo-2-(4-tetrahydropyranyl)pyrimidine 4-Chloro-5-bromo-2-(4-tetrahydropyranyl)pyrimidine 1399482-87-1 C9H10BrClN2O
4-Chloro-5-bromo-2-(cyclohexyl)pyrimidine 4-Chloro-5-bromo-2-(cyclohexyl)pyrimidine 1399482-33-7 C10H12BrClN2
4-Chloro-5-bromo-2-ethylpyrimidine 4-Chloro-5-bromo-2-ethylpyrimidine 1399480-91-1 C6H6BrClN2
4-Chloro-5-methyl-2-(tert-butoxy)pyrimidine 4-Chloro-5-methyl-2-(tert-butoxy)pyrimidine 1563534-43-9 C9H13ClN2O
4-Hydroxy-2-(3-pyridyl)pyridine 4-Hydroxy-2-(3-pyridyl)pyridine 1159815-01-6 C10H8N2O
4-Hydroxy-2-(4-pyridyl)pyridine 4-Hydroxy-2-(4-pyridyl)pyridine 1159818-84-4 C10H8N2O
4-Hydroxy-2-methyl-6-(2-trifluoromethylphenyl)pyrimidine 4-Hydroxy-2-methyl-6-(2-trifluoromethylphenyl)pyrimidine 1159816-12-2 C12H9F3N2O
4-Hydroxy-2-phenyl-6-(2-methyl-4-thiazolyl)pyrimidine 4-Hydroxy-2-phenyl-6-(2-methyl-4-thiazolyl)pyrimidine 1159814-61-5 C14H11N3OS
4-Hydroxy-6-(2-methyl-5-thiazolyl)-2-cyclopropylpyrimidine 4-Hydroxy-6-(2-methyl-5-thiazolyl)-2-cyclopropylpyrimidine 1159815-59-4 C11H11N3OS
4-Hydroxy-6-(3-thienyl)pyrimidine 4-Hydroxy-6-(3-thienyl)pyrimidine 1159818-38-8 C8H6N2OS
4-methyl-2-(oxetan-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 4-methyl-2-(oxetan-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2256758-29-7 C13H20BNO3S
5-(1H-imidazol-1-yl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(1H-imidazol-1-yl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256709-69-8 C14H18BN3O2
5-(2-BROMOPHENYL)PYRIMIDINE 5-(2-BROMOPHENYL)PYRIMIDINE 1162257-14-8 C10H7BrN2
5-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256706-39-3 C15H20BN3O2
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(thiazol-4-yl)pyridin-2(1H)-one 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(thiazol-4-yl)pyridin-2(1H)-one 2256754-93-3 C14H17BN2O3S
5-(4-bromo-1H-imidazol-1-yl-2,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 5-(4-bromo-1H-imidazol-1-yl-2,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2256706-78-0 C14H17BBrN3O2
5-(4-bromophenyl)-2-(methyl-d3)pyrimidine-4,6-d2 5-(4-bromophenyl)-2-(methyl-d3)pyrimidine-4,6-d2 2256712-11-3 C11H9BrN2
5-(ethoxy-d5)pyridin-3-amine 5-(ethoxy-d5)pyridin-3-amine 2259316-12-4 C7H5D5N2O
5-(methyl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 5-(methyl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2241869-88-3 C12H18BNO2
5-(n-Propyl)-3-acetoxypyridine 5-(n-Propyl)-3-acetoxypyridine 1434127-57-7 C10H13NO2
5-(tetrahydro-2H-pyran-2-yl)pyridin-3-amine 5-(tetrahydro-2H-pyran-2-yl)pyridin-3-amine 1622835-92-0 C10H14N2O
5-(tetrahydro-2H-pyran-3-yl)pyrimidin-2-amine 5-(tetrahydro-2H-pyran-3-yl)pyrimidin-2-amine 2167988-24-9 C9H13N3O
5-Amino-2-(3-chlorophenyl)thiazole 5-Amino-2-(3-chlorophenyl)thiazole 1353856-08-2 C9H7ClN2S
5-Amino-2-(3-tolyl)thiazole 5-Amino-2-(3-tolyl)thiazole 1159817-27-2 C10H10N2S
5-bromo-2-(1H-pyrazol-1-yl-d3)pyridine 5-bromo-2-(1H-pyrazol-1-yl-d3)pyridine 2256707-43-2 C8H6BrN3
5-bromo-2-(4-bromophenyl)pyridine-3,4,6-d3 5-bromo-2-(4-bromophenyl)pyridine-3,4,6-d3 2256711-81-4 C11H7Br2N
5-BROMO-2-(FURAN-3-YL)PYRIDIN-4-AMINE 5-BROMO-2-(FURAN-3-YL)PYRIDIN-4-AMINE 1381935-19-8 C9H7BrN2O
5-bromo-2-(tetrahydrofuran-2-yl)pyridine 5-bromo-2-(tetrahydrofuran-2-yl)pyridine 2169075-54-9 C9H10BrNO
5-bromo-2-fluoropyrimidine-4,6-d2 5-bromo-2-fluoropyrimidine-4,6-d2 2259315-65-4 C4H2BrFN2
5-Bromo-4-(iso-propyl)-2-(diethylamino)thiazole 5-Bromo-4-(iso-propyl)-2-(diethylamino)thiazole 1643577-11-0 C10H17BrN2S
5-Bromo-4-(n-propyl)-2-(piperidino)thiazole 5-Bromo-4-(n-propyl)-2-(piperidino)thiazole 1643543-17-2 C11H17BrN2S
5-Bromo-4-cyclopropyl-2-(dimethylamino)thiazole 5-Bromo-4-cyclopropyl-2-(dimethylamino)thiazole 1314356-25-6 C8H11BrN2S
5-Bromo-4-methyl-1-(cyclopropyl)-1H-pyrazole 5-Bromo-4-methyl-1-(cyclopropyl)-1H-pyrazole 1622842-68-5 C7H9BrN2
5-bromopyrimidine-2-carbonitrile-4,6-d2 5-bromopyrimidine-2-carbonitrile-4,6-d2 2259315-64-3 C5H2BrN3
5-Hydroxy-2-(4-ethylphenyl)thiazole 5-Hydroxy-2-(4-ethylphenyl)thiazole 1159814-63-7 C11H11NOS
6-(2-METHYLPHENYL)PYRIDIN-3-AMINE 6-(2-METHYLPHENYL)PYRIDIN-3-AMINE 1226158-23-1 C12H12N2
6-(3-BROMOPHENYL)PYRIDIN-3-AMINE 6-(3-BROMOPHENYL)PYRIDIN-3-AMINE 1369347-29-4 C11H9BrN2
6-(methoxy-d3)pyridin-2,4,5-d3-3-amine 6-(methoxy-d3)pyridin-2,4,5-d3-3-amine 2256707-65-8 C6H8N2O
6-(tetrahydrofuran-3-yl)pyridazin-3-ol 6-(tetrahydrofuran-3-yl)pyridazin-3-ol 1603550-57-7 C8H10N2O2
6-(THIOPHEN-2-YL)PYRIDIN-2-AMINE 6-(THIOPHEN-2-YL)PYRIDIN-2-AMINE 1159817-98-7 C9H8N2S
IMIDAZO[1,2-A]PYRIDINE-5-BORONIC ACID PINACOL ESTER IMIDAZO[1,2-A]PYRIDINE-5-BORONIC ACID PINACOL ESTER 1419554-16-7 C13H17BN2O2
Methyl 3,4-dibromopyridine-2-carboxylate Methyl 3,4-dibromopyridine-2-carboxylate 1399482-29-1 C7H5Br2NO2
N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl-3,5,6-d3)pivalamide N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl-3,5,6-d3)pivalamide 2241870-35-7 C16H25BN2O3
TERT-BUTYL 4-(2-BROMOPYRIDIN-3-YL)PIPERIDINE-1-CARBOXYLATE TERT-BUTYL 4-(2-BROMOPYRIDIN-3-YL)PIPERIDINE-1-CARBOXYLATE 1563528-60-8 C15H21BrN2O2
TERT-BUTYL 4-(3-AMINOPYRIDIN-4-YL)PIPERIDINE-1-CARBOXYLATE TERT-BUTYL 4-(3-AMINOPYRIDIN-4-YL)PIPERIDINE-1-CARBOXYLATE 1245915-21-2 C15H23N3O2
TERT-BUTYL 4-(6-BROMOPYRIMIDIN-4-YL)PIPERIDINE-1-CARBOXYLATE TERT-BUTYL 4-(6-BROMOPYRIMIDIN-4-YL)PIPERIDINE-1-CARBOXYLATE 1622842-80-1 C14H20BrN3O2
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
tert-butyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate tert-butyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate C17H30BNO4
3-Bromo-4-(oxetan-3-yloxy)pyridine 3-Bromo-4-(oxetan-3-yloxy)pyridine 1594780-20-7 C8H8BrNO2
2-Amino-4-(pyrrolidin-2-yl)pyridine 2-Amino-4-(pyrrolidin-2-yl)pyridine 1270485-39-6 C9H13N3
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
2-(Pyrrolidin-3-yl)-6-(trifluoromethyl)pyridine 2-(Pyrrolidin-3-yl)-6-(trifluoromethyl)pyridine 1256812-97-1 C10H11F3N2
5-bromo-2-methoxy-3-(tetrahydrofuran-2-yl)pyridine 5-bromo-2-methoxy-3-(tetrahydrofuran-2-yl)pyridine 2294944-99-1 C10H12BrNO2
2-Chloro-5-(tetrahydrofuran-2-yl)pyridine 2-Chloro-5-(tetrahydrofuran-2-yl)pyridine 1353853-66-3 C9H10ClNO
2-Amino-6-(tetrahydrofuran-2-yl)pyridine 2-Amino-6-(tetrahydrofuran-2-yl)pyridine 1353853-51-6 C9H12N2O
3-(3-Tetrahydrofuranyl)phenol 3-(3-Tetrahydrofuranyl)phenol 1353853-47-0 C10H12O2
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
Furo[3,2-b]pyridine-3-carboxylic acid Furo[3,2-b]pyridine-3-carboxylic acid 1504227-31-9 C8H5NO3
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
Pyridine, 4-bromo-3-cyclopropyl-2-methoxy- Pyridine, 4-bromo-3-cyclopropyl-2-methoxy- 1823919-36-3 C9H10BrNO
5-Bromo-1-(methyl-d3)-pyridin-2-one 5-Bromo-1-(methyl-d3)-pyridin-2-one 1611464-91-5 C6H6BrNO
Pyridine, 2-ethyl-3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Pyridine, 2-ethyl-3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1220220-23-4 C13H19BFNO2
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
[2,2'-Bipyridin]-4-amine, 6'-bromo- [2,2'-Bipyridin]-4-amine, 6'-bromo- 1185306-13-1 C10H8BrN3
3-Pyridinemethanol, 6-(6-chloro-2-pyrazinyl)- 3-Pyridinemethanol, 6-(6-chloro-2-pyrazinyl)- 1185306-35-7 C10H8ClN3O
Thiophene, 3-bromo-5-chloro-2-methyl- Thiophene, 3-bromo-5-chloro-2-methyl- 61074-71-3 C5H4BrClS
4-Thiazolamine, 5-cyclohexyl- 4-Thiazolamine, 5-cyclohexyl- 1374665-42-5 C9H14N2S
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
2-(3-BROMO-4-FLUORO-PHENYL)-1H-IMIDAZOLE 2-(3-BROMO-4-FLUORO-PHENYL)-1H-IMIDAZOLE 1368667-05-3 C9H6BrFN2
1H-1,4,7-Triazonine, 1,1'-(1,2-ethanediyl)bis[octahydro-4,7-dimethyl- 1H-1,4,7-Triazonine, 1,1'-(1,2-ethanediyl)bis[octahydro-4,7-dimethyl- 151558-50-8 C18H40N6
Quinazoline, 4-bromo-2-chloro- Quinazoline, 4-bromo-2-chloro- 1379302-01-8 C8H4BrClN2
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
1,3,5-Triazine-1,3,5(2H,4H,6H)-triacetic acid, 2,4,6-trioxo- 1,3,5-Triazine-1,3,5(2H,4H,6H)-triacetic acid, 2,4,6-trioxo- 1968-52-1 C9H9N3O9
Pyridine, 2-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Pyridine, 2-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1402240-81-6 C17H26BNO2
Pomalidomide-C5-NH2 hydrochloride Pomalidomide-C5-NH2 hydrochloride 2375194-03-7 C18H23ClN4O4
2-Pyridinamine, 5-(3-oxetanyloxy)- 2-Pyridinamine, 5-(3-oxetanyloxy)- 1934912-87-4 C8H10N2O2
4-Pyridinamine, N-cyclopentyl-2-fluoro- 4-Pyridinamine, N-cyclopentyl-2-fluoro- 1566297-18-4 C10H13FN2
1H-1,2,3-Triazole, 5-bromo-1-(1-methylethyl)- 1H-1,2,3-Triazole, 5-bromo-1-(1-methylethyl)- 1781570-21-5 C5H8BrN3
Pyridine, 2-(1-bromo-1-methylethyl)- Pyridine, 2-(1-bromo-1-methylethyl)- 40473-18-5 C8H10BrN
Thiazole, 5-bromo-4-methoxy- Thiazole, 5-bromo-4-methoxy- 2228818-64-0 C4H4BrNOS
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