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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-Amino-2-(3-tolyl)thiazole 4-Amino-2-(3-tolyl)thiazole 123970-59-2 C10H10N2S
4-Amino-2-(5-pyrimidyl)thiazole 4-Amino-2-(5-pyrimidyl)thiazole 1159816-89-3 C7H6N4S
4-Amino-2-chloro-3-bromo-5-(2-furyl)pyridine 4-Amino-2-chloro-3-bromo-5-(2-furyl)pyridine 1563533-78-7 C9H6BrClN2O
4-Amino-2-chloro-3-bromo-5-(3,4-difluorophenyl)pyridine 4-Amino-2-chloro-3-bromo-5-(3,4-difluorophenyl)pyridine 1563534-74-6 C11H6BrClF2N2
4-Amino-2-chloro-3-bromo-5-(4-tolyl)pyridine 4-Amino-2-chloro-3-bromo-5-(4-tolyl)pyridine 1563531-95-2 C12H10BrClN2
4-Amino-2-chloro-3-bromo-5-(iso-propyl)pyridine 4-Amino-2-chloro-3-bromo-5-(iso-propyl)pyridine 1563532-99-9 C8H10BrClN2
4-Amino-2-methyl-6-(2-pyridyl)pyrimidine 4-Amino-2-methyl-6-(2-pyridyl)pyrimidine 90916-54-4 C10H10N4
4-Amino-2-methyl-6-(4-thiazolyl)pyrimidine 4-Amino-2-methyl-6-(4-thiazolyl)pyrimidine 1159818-15-1 C8H8N4S
4-AMINO-3-(2-METHYLIMIDAZOL-1-YL)PYRIDINE 4-AMINO-3-(2-METHYLIMIDAZOL-1-YL)PYRIDINE 1466861-97-1 C9H10N4
4-AMINO-3-(3-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 4-AMINO-3-(3-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 1369243-17-3 C9H10N4
4-Amino-3-(methylethylamino)pyridine 4-Amino-3-(methylethylamino)pyridine 1563528-88-0 C8H13N3
4-Amino-3,5-dibromo-2-(3,5-difluorophenyl)pyridine 4-Amino-3,5-dibromo-2-(3,5-difluorophenyl)pyridine 1563530-61-9 C11H6Br2F2N2
4-Amino-3,5-dibromo-2-(3-methoxyphenyl)pyridine 4-Amino-3,5-dibromo-2-(3-methoxyphenyl)pyridine 1563528-81-3 C12H10Br2N2O
4-Amino-3,5-dibromo-2-(4-trifluoromethylphenyl)pyridine 4-Amino-3,5-dibromo-2-(4-trifluoromethylphenyl)pyridine 1563533-90-3 C12H7Br2F3N2
4-Amino-3,5-dibromo-2-(cyclopentoxy)pyridine 4-Amino-3,5-dibromo-2-(cyclopentoxy)pyridine 1563530-66-4 C10H12Br2N2O
4-Amino-3,5-dibromo-2-(iso-propyl)pyridine 4-Amino-3,5-dibromo-2-(iso-propyl)pyridine 1563528-86-8 C8H10Br2N2
4-Amino-3,5-dibromo-2-diethylaminopyridine 4-Amino-3,5-dibromo-2-diethylaminopyridine 1563532-40-0 C9H13Br2N3
4-Amino-3,5-dibromo-2-phenylpyridine 4-Amino-3,5-dibromo-2-phenylpyridine 1563529-96-3 C11H8Br2N2
4-Amino-3-bromo-2-(iso-butyl)pyridine 4-Amino-3-bromo-2-(iso-butyl)pyridine 1563532-44-4 C9H13BrN2
4-AMINO-3-BROMO-2-(TETRAHYDROFURAN-3-YLOXY)PYRIDINE 4-AMINO-3-BROMO-2-(TETRAHYDROFURAN-3-YLOXY)PYRIDINE 1563532-39-7 C9H11BrN2O2
4-Amino-3-bromo-6-(iso-butyl)pyridine 4-Amino-3-bromo-6-(iso-butyl)pyridine 1563530-75-5 C9H13BrN2
4-Amino-3-bromo-6-(tetrahydrofuran-3yloxy)pyridine 4-Amino-3-bromo-6-(tetrahydrofuran-3yloxy)pyridine 1563530-24-4 C9H11BrN2O2
4-Amino-6-(2-furyl)pyrimidine 4-Amino-6-(2-furyl)pyrimidine 1159817-77-2 C8H7N3O
4-Bromo-1-(2-amino-4-pyridyl)pyrazole 4-Bromo-1-(2-amino-4-pyridyl)pyrazole 1363254-28-7 C8H7BrN4
4-Bromo-1-(2-methyl-4-pyridyl)pyrazole 4-Bromo-1-(2-methyl-4-pyridyl)pyrazole 1353855-11-4 C9H8BrN3
4-Bromo-1-(4-ethylphenyl)pyrazole 4-Bromo-1-(4-ethylphenyl)pyrazole 1353856-50-4 C11H11BrN2
4-Bromo-1-(oxan-3-yl)-1H-1,2,3-triazole 4-Bromo-1-(oxan-3-yl)-1H-1,2,3-triazole 1622834-22-3 C7H10BrN3O
4-Bromo-1-propyl-1H-1,2,3-triazole 4-Bromo-1-propyl-1H-1,2,3-triazole 1260672-11-4 C5H8BrN3
4-Bromo-2-(2-furyl)thiazole 4-Bromo-2-(2-furyl)thiazole 1142194-92-0 C7H4BrNOS
4-Bromo-2-(2-tolyl)pyridine 4-Bromo-2-(2-tolyl)pyridine 1142194-13-5 C12H10BrN
4-Bromo-2-(3,4-difluorophenyl)pyridine 4-Bromo-2-(3,4-difluorophenyl)pyridine 1215074-29-5 C11H6BrF2N
4-Bromo-2-(3-furyl)pyridine 4-Bromo-2-(3-furyl)pyridine 1142194-20-4 C9H6BrNO
4-Bromo-2-(4-methylpiperidino)pyrimidine 4-Bromo-2-(4-methylpiperidino)pyrimidine 1086381-77-2 C10H14BrN3
4-Bromo-2-(iso-butyl)thiazole 4-Bromo-2-(iso-butyl)thiazole 454702-94-4 C7H10BrNS
4-Bromo-2-(n-propyl)thiazole 4-Bromo-2-(n-propyl)thiazole 1142196-34-6 C6H8BrNS
4-Bromo-2-(sec-butyl)pyridine 4-Bromo-2-(sec-butyl)pyridine 1374665-90-3 C9H12BrN
4-bromo-2-(tetrahydrofuran-2-yl)pyrimidine 4-bromo-2-(tetrahydrofuran-2-yl)pyrimidine 2222934-94-1 C8H9BrN2O
4-Bromo-2-hydroxy-5-(iso-propyl)pyrimidine 4-Bromo-2-hydroxy-5-(iso-propyl)pyrimidine 1381934-91-3 C7H9BrN2O
4-bromo-3-(1H-pyrazol-1-yl-d3)pyridine-2,5,6-d3 4-bromo-3-(1H-pyrazol-1-yl-d3)pyridine-2,5,6-d3 2256707-35-2 C8H6BrN3
4-Bromo-3-(2-fluorophenyl)pyridine 4-Bromo-3-(2-fluorophenyl)pyridine 1374665-54-9 C11H7BrFN
4-Bromo-3-(3-furyl)pyridine 4-Bromo-3-(3-furyl)pyridine 1374664-63-7 C9H6BrNO
4-Bromo-3-(3-tolyl)pyridine 4-Bromo-3-(3-tolyl)pyridine 1374665-85-6 C12H10BrN
4-Bromo-3-(diethylamino)pyridine 4-Bromo-3-(diethylamino)pyridine 1563534-99-5 C9H13BrN2
4-Bromo-3-amino-6-(2-methylpiperidin-1-yl)pyridine 4-Bromo-3-amino-6-(2-methylpiperidin-1-yl)pyridine 1381944-04-2 C11H16BrN3
4-Bromo-3-amino-6-(3-trifluoromethylphenyl)pyridine 4-Bromo-3-amino-6-(3-trifluoromethylphenyl)pyridine 1381934-68-4 C12H8BrF3N2
4-Bromo-3-amino-6-(4-methyl-1H-pyrazol-1-yl)pyridine 4-Bromo-3-amino-6-(4-methyl-1H-pyrazol-1-yl)pyridine 1381938-21-1 C9H9BrN4
4-Bromo-3-amino-6-(piperazin-1-yl)pyridine 4-Bromo-3-amino-6-(piperazin-1-yl)pyridine 1381944-07-5 C9H13BrN4
4-bromo-5-fluoro-2-(methyl-d3)pyridine 4-bromo-5-fluoro-2-(methyl-d3)pyridine 2294957-79-0 C6H5BrFN
4-Bromo-6-(2-pyridyl)pyrimidine 4-Bromo-6-(2-pyridyl)pyrimidine 1159818-66-2 C9H6BrN3
4-Bromo-6-(4-fluoro-2-methylphenyl)pyrimidine 4-Bromo-6-(4-fluoro-2-methylphenyl)pyrimidine 1142194-04-4 C11H8BrFN2
4-bromopyrimidin-5,6-d2-2-ol 4-bromopyrimidin-5,6-d2-2-ol 2241865-61-0 C4H3BrN2O
4-chloro-2-(tetrahydro-2H-pyran-2-yl)pyrimidine 4-chloro-2-(tetrahydro-2H-pyran-2-yl)pyrimidine 2104183-61-9 C9H11ClN2O
4-Chloro-2-methyl-6-(2-methyl-5-thiazolyl)pyrimidine 4-Chloro-2-methyl-6-(2-methyl-5-thiazolyl)pyrimidine 1159819-11-0 C9H8ClN3S
4-Chloro-2-methyl-6-(4-thiazolyl)pyrimidine 4-Chloro-2-methyl-6-(4-thiazolyl)pyrimidine 1159818-09-3 C8H6ClN3S
4-Chloro-3-(4-aminophenyl)pyridine 4-Chloro-3-(4-aminophenyl)pyridine 1563533-58-3 C11H9ClN2
4-Chloro-5-bromo-2-(3-furyl)pyrimidine 4-Chloro-5-bromo-2-(3-furyl)pyrimidine 1399481-64-1 C8H4BrClN2O
4-Chloro-5-bromo-2-(3-tolyl)pyrimidine 4-Chloro-5-bromo-2-(3-tolyl)pyrimidine 1399480-05-7 C11H8BrClN2
4-Chloro-5-bromo-2-(cyclopentoxy)pyrimidine 4-Chloro-5-bromo-2-(cyclopentoxy)pyrimidine 1399481-55-0 C9H10BrClN2O
4-Chloro-5-bromo-2-(ethoxy)pyrimidine 4-Chloro-5-bromo-2-(ethoxy)pyrimidine 1399481-71-0 C6H6BrClN2O
4-Chloro-6-(2-fluorophenyl)-2-cyclopropylpyrimidine 4-Chloro-6-(2-fluorophenyl)-2-cyclopropylpyrimidine 1159819-69-8 C13H10ClFN2
4-Chloro-6-methyl-2-(iso-propoxy)pyrimidine 4-Chloro-6-methyl-2-(iso-propoxy)pyrimidine 932701-89-8 C8H11ClN2O
4-fluoro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl)pyridine 4-fluoro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl)pyridine 2256755-48-1 C14H17BFN3O2
4-Hydroxy-2-(5-pyrimidyl)pyridine 4-Hydroxy-2-(5-pyrimidyl)pyridine 1159819-02-9 C9H7N3O
4-Hydroxy-2-phenyl-6-(5-thiazolyl)pyrimidine 4-Hydroxy-2-phenyl-6-(5-thiazolyl)pyrimidine 1159819-63-2 C13H9N3OS
4-Hydroxy-6-(5-pyrimidyl)-2-cyclopropylpyrimidine 4-Hydroxy-6-(5-pyrimidyl)-2-cyclopropylpyrimidine 1159814-94-4 C11H10N4O
4-Hydroxy-6-(piperidin-3-yl)pyridine 4-Hydroxy-6-(piperidin-3-yl)pyridine 1337345-89-7 C10H14N2O
4-methyl-2-((tetrahydrofuran-3-yl)oxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 4-methyl-2-((tetrahydrofuran-3-yl)oxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2256758-16-2 C14H22BNO4S
5-(3-bromophenyl)-2-(methyl-d3)pyridine-3,4,6-d3 5-(3-bromophenyl)-2-(methyl-d3)pyridine-3,4,6-d3 2256711-99-4 C12H10BrN
5-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridin-2-amine 5-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridin-2-amine 2294949-60-1 C9H10N4
5-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 5-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2256706-54-2 C14H17BBrN3O2
5-(4-bromophenyl)-2-chloropyridine-3,4,6-d3 5-(4-bromophenyl)-2-chloropyridine-3,4,6-d3 2256711-93-8 C11H7BrClN
5-(ethoxy-d5)pyridin-2,4,6-d3-3-amine 5-(ethoxy-d5)pyridin-2,4,6-d3-3-amine 2259316-22-6 C7H10N2O
5-(tetrahydro-2H-pyran-4-yl)pyrimidin-2-ol 5-(tetrahydro-2H-pyran-4-yl)pyrimidin-2-ol 2222933-79-9 C9H12N2O2
5,5'-DIISOPROPYL-2,2'-BIPYRIDINE 5,5'-DIISOPROPYL-2,2'-BIPYRIDINE 1434127-80-6 C16H20N2
5-Amino-2-(3-Furyl)thiazole 5-Amino-2-(3-Furyl)thiazole 1159817-69-2 C7H6N2OS
5-BROMO-2-(2-CHLOROPHENYL)PYRIDIN-4-AMINE 5-BROMO-2-(2-CHLOROPHENYL)PYRIDIN-4-AMINE 1381942-75-1 C11H8BrClN2
5-Bromo-2-(2-fluorophenyl)thiazole 5-Bromo-2-(2-fluorophenyl)thiazole 1159821-79-0 C9H5BrFNS
5-BROMO-2-(3-CHLOROPHENYL)PYRIDIN-4-AMINE 5-BROMO-2-(3-CHLOROPHENYL)PYRIDIN-4-AMINE 1381943-87-8 C11H8BrClN2
5-BROMO-2-(3-HYDROXYPIPERIDIN-1-YL)PYRIDIN-4-AMINE 5-BROMO-2-(3-HYDROXYPIPERIDIN-1-YL)PYRIDIN-4-AMINE 1381937-89-8 C10H14BrN3O
5-Bromo-2-(4-methoxyphenyl)thiazole 5-Bromo-2-(4-methoxyphenyl)thiazole 778581-58-1 C10H8BrNOS
5-BROMO-2-(4-METHYLPIPERIDIN-1-YL)PYRIDIN-4-AMINE 5-BROMO-2-(4-METHYLPIPERIDIN-1-YL)PYRIDIN-4-AMINE 1381942-34-2 C11H16BrN3
5-bromo-2-(methyl-d3)pyridin-3,6-d2-4-amine 5-bromo-2-(methyl-d3)pyridin-3,6-d2-4-amine 2294947-85-4 C6H7BrN2
5-bromo-2-(tetrahydro-2H-pyran-2-yl)pyridine 5-bromo-2-(tetrahydro-2H-pyran-2-yl)pyridine 1622835-02-2 C10H12BrNO
5-Bromo-2-(thiazol-2-yl)pyridine 5-Bromo-2-(thiazol-2-yl)pyridine 1005196-12-2 C8H5BrN2S
5-Bromo-2-methyl-4-(iso-propyl)thiazole 5-Bromo-2-methyl-4-(iso-propyl)thiazole 1522901-38-7 C7H10BrNS
5-Bromo-4-(iso-propyl)-2-(morpholino)thiazole 5-Bromo-4-(iso-propyl)-2-(morpholino)thiazole 1643576-18-4 C10H15BrN2OS
5-Bromo-4-(n-propyl)-2-ethoxythiazole 5-Bromo-4-(n-propyl)-2-ethoxythiazole 1643564-51-5 C8H12BrNOS
5-Bromo-4-cyclopropyl-2-methoxythiazole 5-Bromo-4-cyclopropyl-2-methoxythiazole 1314357-25-9 C7H8BrNOS
5-Bromo-4-methyl-2-(dimethylamino)thiazole 5-Bromo-4-methyl-2-(dimethylamino)thiazole 874508-77-7 C6H9BrN2S
5-bromopyrimidin-4,6-d2-2-amine 5-bromopyrimidin-4,6-d2-2-amine 2241865-56-3 C4H4BrN3
5-Hydroxy-2-(4-tert-butylphenyl)thiazole 5-Hydroxy-2-(4-tert-butylphenyl)thiazole 1159822-07-7 C13H15NOS
5-PROPYLPYRIDIN-3-AMINE 5-PROPYLPYRIDIN-3-AMINE 1314356-71-2 C8H12N2
6-(methoxy-d3)pyridin-3,4,5-d3-2-amine 6-(methoxy-d3)pyridin-3,4,5-d3-2-amine 2256707-67-0 C6H8N2O
6-(oxetan-3-yl)pyridin-2-amine 6-(oxetan-3-yl)pyridin-2-amine 2222934-01-0 C8H10N2O
6-(tetrahydro-2H-pyran-2-yl)pyridin-3-amine 6-(tetrahydro-2H-pyran-2-yl)pyridin-3-amine 1622835-67-9 C10H14N2O
6-(tetrahydro-2H-pyran-3-yl)pyridin-3-amine 6-(tetrahydro-2H-pyran-3-yl)pyridin-3-amine 1889918-71-1 C10H14N2O
6-(tetrahydrofuran-3-yl)pyridin-3-amine 6-(tetrahydrofuran-3-yl)pyridin-3-amine 1440427-99-5 C9H12N2O
6,6'-DIISOPROPYL-2,2'-BIPYRIDINE 6,6'-DIISOPROPYL-2,2'-BIPYRIDINE 90334-61-5 C16H20N2
6-chloropyrimidin-2,5-d2-4-amine 6-chloropyrimidin-2,5-d2-4-amine 2259315-72-3 C4H4ClN3
6-cyclopropyl-N-ethyl-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 6-cyclopropyl-N-ethyl-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 2256754-86-4 C17H27BN2O2
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