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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-(tert-butoxy)-4-fluoropyridine 2-(tert-butoxy)-4-fluoropyridine 2256748-02-2 C9H12FNO
1-(4-fluoropyridin-2-yl)-1H-pyrazol-4-amine 1-(4-fluoropyridin-2-yl)-1H-pyrazol-4-amine 2256748-13-5 C8H7FN4
6-(oxetan-3-yloxy)pyridin-2-amine 6-(oxetan-3-yloxy)pyridin-2-amine 1602836-35-0 C8H10N2O2
1-(5-fluoropyridin-2-yl)-1H-imidazol-4-amine 1-(5-fluoropyridin-2-yl)-1H-imidazol-4-amine 2256748-19-1 C8H7FN4
5-bromo-2-cyclohexyl-4-methylpyrimidine 5-bromo-2-cyclohexyl-4-methylpyrimidine 1780321-24-5 C11H15BrN2
5-bromo-4-methyl-2-(4l2-piperazin-1-yl)pyrimidine 5-bromo-4-methyl-2-(4l2-piperazin-1-yl)pyrimidine 1892822-63-7 C9H13BrN4
2-(4-bromo-1H-imidazol-2-yl)-4-fluoropyridine 2-(4-bromo-1H-imidazol-2-yl)-4-fluoropyridine 2256748-22-6 C8H5BrFN3
4-bromo-2-(tert-butyl)-6-(trifluoromethyl)pyridine 4-bromo-2-(tert-butyl)-6-(trifluoromethyl)pyridine 2460494-66-8 C10H11BrF3N
4-chloro-2-isobutyl-6-(trifluoromethyl)pyridine 4-chloro-2-isobutyl-6-(trifluoromethyl)pyridine 2460501-26-0 C10H11ClF3N
2-isobutyl-6-methylpyridin-4-amine 2-isobutyl-6-methylpyridin-4-amine 2460493-95-0 C10H16N2
2-cyclopropyl-1,10-phenanthroline 2-cyclopropyl-1,10-phenanthroline 2460491-26-1 C15H12N2
4-bromo-2-methyl-6-(tetrahydrofuran-2-yl)pyridine 4-bromo-2-methyl-6-(tetrahydrofuran-2-yl)pyridine 2460500-65-4 C10H12BrNO
2-bromo-4-ethyl-6-methylpyridine 2-bromo-4-ethyl-6-methylpyridine 1541290-38-3 C8H10BrN
5-amino-3-(tert-butyl)pyridin-2(1H)-one 5-amino-3-(tert-butyl)pyridin-2(1H)-one 2460494-18-0 C9H14N2O
3-bromo-5-ethyl-4-methoxypyridine 3-bromo-5-ethyl-4-methoxypyridine 2460500-96-1 C8H10BrNO
3-bromo-4-(thiophen-3-yl)-4H-1,2,4-triazole 3-bromo-4-(thiophen-3-yl)-4H-1,2,4-triazole 2460494-13-5 C6H4BrN3S
3-(3-bromo-4H-1,2,4-triazol-4-yl)pyridine 3-(3-bromo-4H-1,2,4-triazol-4-yl)pyridine 2460494-55-5 C7H5BrN4
3-bromo-4-(4-fluorophenyl)-4H-1,2,4-triazole 3-bromo-4-(4-fluorophenyl)-4H-1,2,4-triazole 2460491-65-8 C8H5BrFN3
4-(2-fluorophenyl)-4H-1,2,4-triazol-3-amine 4-(2-fluorophenyl)-4H-1,2,4-triazol-3-amine 2460494-65-7 C8H7FN4
4-(sec-butyl)-4H-1,2,4-triazol-3-amine 4-(sec-butyl)-4H-1,2,4-triazol-3-amine 2460492-37-7 C6H12N4
3-bromo-4-ethyl-5-methyl-4H-1,2,4-triazole 3-bromo-4-ethyl-5-methyl-4H-1,2,4-triazole 2460491-85-2 C5H8BrN3
3-bromo-5-(3-methoxyphenyl)-4H-1,2,4-triazole 3-bromo-5-(3-methoxyphenyl)-4H-1,2,4-triazole 1783359-29-4 C9H8BrN3O
3-bromo-5-(4-(trifluoromethyl)phenyl)-4H-1,2,4-triazole 3-bromo-5-(4-(trifluoromethyl)phenyl)-4H-1,2,4-triazole 2460492-76-4 C9H5BrF3N3
5-bromo-4-(2-(trifluoromethyl)phenyl)-1H-1,2,3-triazole 5-bromo-4-(2-(trifluoromethyl)phenyl)-1H-1,2,3-triazole 2460491-82-9 C9H5BrF3N3
5-bromo-4-(thiophen-2-yl)-1H-1,2,3-triazole 5-bromo-4-(thiophen-2-yl)-1H-1,2,3-triazole 2460490-21-3 C6H4BrN3S
5-bromo-4-(4-chlorophenyl)-1H-1,2,3-triazole 5-bromo-4-(4-chlorophenyl)-1H-1,2,3-triazole 2091651-15-7 C8H5BrClN3
2-(1H-1,2,3-triazol-5-yl)benzonitrile 2-(1H-1,2,3-triazol-5-yl)benzonitrile 1620655-94-8 C9H6N4
4-bromo-5-cyclopropyl-1-methyl-1H-1,2,3-triazole 4-bromo-5-cyclopropyl-1-methyl-1H-1,2,3-triazole 2460493-14-3 C6H8BrN3
3-(thiophen-3-yl)-4H-1,2,4-triazole 3-(thiophen-3-yl)-4H-1,2,4-triazole 2460492-50-4 C6H5N3S
3-(4-bromo-3-methyl-1H-pyrazol-1-yl)pyridine 3-(4-bromo-3-methyl-1H-pyrazol-1-yl)pyridine 2460492-32-2 C9H8BrN3
3-methyl-1-(pyridazin-3-yl)-1H-pyrazol-4-amine 3-methyl-1-(pyridazin-3-yl)-1H-pyrazol-4-amine 2111530-12-0 C8H9N5
4-(2-bromo-5-iodophenyl)morpholine 4-(2-bromo-5-iodophenyl)morpholine 1690556-75-2 C10H11BrINO
1-(4-chloropyrimidin-2-yl)azetidin-3-ol 1-(4-chloropyrimidin-2-yl)azetidin-3-ol 2600399-89-9 C7H8ClN3O
3-bromo-2-fluoro-6-(m-tolyl)pyridine 3-bromo-2-fluoro-6-(m-tolyl)pyridine 2600400-00-6 C12H9BrFN
3-bromo-2-methyl-6-(o-tolyl)pyridine 3-bromo-2-methyl-6-(o-tolyl)pyridine 2071190-43-5 C13H12BrN
2-(5-bromo-6-methylpyridin-2-yl)thiazole 2-(5-bromo-6-methylpyridin-2-yl)thiazole 1334646-89-7 C9H7BrN2S
8-methylimidazo[1,2-b]pyridazin-6-amine 8-methylimidazo[1,2-b]pyridazin-6-amine 2645419-76-5 C7H8N4
4-bromo-2-cyclobutyl-6-cyclopropylpyridine 4-bromo-2-cyclobutyl-6-cyclopropylpyridine 2645413-26-7 C12H14BrN
4-bromo-2-cyclopropyl-6-isopropylpyridine 4-bromo-2-cyclopropyl-6-isopropylpyridine 2645414-04-4 C11H14BrN
3-bromo-5-(2,2-difluoro-1-methylcyclopropyl)pyridine 3-bromo-5-(2,2-difluoro-1-methylcyclopropyl)pyridine 2645413-30-3 C9H8BrF2N
3-bromo-5-(2,2-difluorocyclopropyl)pyridine 3-bromo-5-(2,2-difluorocyclopropyl)pyridine 2385787-07-3 C8H6BrF2N
4-bromo-1-(p-tolyl)-1H-1,2,3-triazole 4-bromo-1-(p-tolyl)-1H-1,2,3-triazole 2256748-67-9 C9H8BrN3
4-bromo-1-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazole 4-bromo-1-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazole 2256748-72-6 C9H5BrF3N3
4-bromo-1-(3-methoxyphenyl)-1H-1,2,3-triazole 4-bromo-1-(3-methoxyphenyl)-1H-1,2,3-triazole 2256748-75-9 C9H8BrN3O
3,5-dimethyl-2-(trifluoromethyl)pyridin-4-amine 3,5-dimethyl-2-(trifluoromethyl)pyridin-4-amine 2645411-69-2 C8H9F3N2
4-(4-bromo-1H-1,2,3-triazol-1-yl)benzonitrile 4-(4-bromo-1H-1,2,3-triazol-1-yl)benzonitrile 2256748-79-3 C9H5BrN4
2-bromo-4-((tetrahydro-2H-pyran-2-yl)methoxy)pyridine 2-bromo-4-((tetrahydro-2H-pyran-2-yl)methoxy)pyridine 2645413-88-1 C11H14BrNO2
4-((2,4-dimethoxybenzyl)oxy)-2-fluoropyridine 4-((2,4-dimethoxybenzyl)oxy)-2-fluoropyridine 2645419-85-6 C14H14FNO3
2-bromo-6-(3-methylbicyclo[1.1.1]pentan-1-yl)pyridine 2-bromo-6-(3-methylbicyclo[1.1.1]pentan-1-yl)pyridine 2697155-12-5 C11H12BrN
5-bromo-2-(3-methylbicyclo[1.1.1]pentan-1-yl)pyrimidine 5-bromo-2-(3-methylbicyclo[1.1.1]pentan-1-yl)pyrimidine 2697155-01-2 C10H11BrN2
1-(pyridazin-3-yl)-1H-1,2,3-triazol-4-amine 1-(pyridazin-3-yl)-1H-1,2,3-triazol-4-amine 2256754-43-3 C6H6N6
4-(4-bromo-1H-1,2,3-triazol-1-yl)-2-methylpyridine 4-(4-bromo-1H-1,2,3-triazol-1-yl)-2-methylpyridine 2256754-47-7 C8H7BrN4
2-(4-bromothiazol-2-yl)oxazole 2-(4-bromothiazol-2-yl)oxazole 1700626-70-5 C6H3BrN2OS
4-bromo-2-(pyrimidin-4-yl)oxazole 4-bromo-2-(pyrimidin-4-yl)oxazole 2697162-27-7 C7H4BrN3O
2-bromo-6-methyl-4-(piperidin-3-yl)pyridine 2-bromo-6-methyl-4-(piperidin-3-yl)pyridine 2768657-86-7 C11H15BrN2
2-methoxy-6-(piperidin-3-yl)pyridin-4-amine 2-methoxy-6-(piperidin-3-yl)pyridin-4-amine 2768654-47-1 C11H17N3O
8-isopropylquinoxalin-5-amine 8-isopropylquinoxalin-5-amine 2806720-60-3 C11H13N3
8-(oxetan-3-yl)quinoxalin-5-ol 8-(oxetan-3-yl)quinoxalin-5-ol 2806719-94-6 C11H10N2O2
tert-butyl 4-(2-bromopyrimidin-4-yl)-3-methylpiperidine-1-carboxylate tert-butyl 4-(2-bromopyrimidin-4-yl)-3-methylpiperidine-1-carboxylate 2806719-06-0 C15H22BrN3O2
2-(2-isopropylphenyl)morpholine 2-(2-isopropylphenyl)morpholine 1510773-67-7
3-(6-bromopyridin-2-yl)tetrahydro-4H-pyran-4-one 3-(6-bromopyridin-2-yl)tetrahydro-4H-pyran-4-one 2806729-62-2 C10H10BrNO2
2-(6-chloropyridazin-3-yl)tetrahydro-4H-pyran-4-one 2-(6-chloropyridazin-3-yl)tetrahydro-4H-pyran-4-one 2358969-02-3 C9H9ClN2O2
2-(2-hydroxypyrimidin-5-yl)tetrahydro-4H-pyran-4-one 2-(2-hydroxypyrimidin-5-yl)tetrahydro-4H-pyran-4-one 2806729-64-4 C9H10N2O3
2-(6-aminopyridin-3-yl)tetrahydro-4H-pyran-4-one 2-(6-aminopyridin-3-yl)tetrahydro-4H-pyran-4-one 2806720-15-8 C10H12N2O2
3-(5-hydroxypyridin-2-yl)tetrahydro-4H-pyran-4-one 3-(5-hydroxypyridin-2-yl)tetrahydro-4H-pyran-4-one 2806720-20-5 C10H11NO3
3-(6-hydroxypyridazin-3-yl)tetrahydro-4H-pyran-4-one 3-(6-hydroxypyridazin-3-yl)tetrahydro-4H-pyran-4-one 2806719-39-9 C9H10N2O3
3-(4-bromopyridin-2-yl)tetrahydro-4H-pyran-4-one 3-(4-bromopyridin-2-yl)tetrahydro-4H-pyran-4-one 2806721-23-1 C10H10BrNO2
2-bromo-4-(4,4-difluoropiperidin-1-yl)pyrimidine 2-bromo-4-(4,4-difluoropiperidin-1-yl)pyrimidine 2806719-25-3 C9H10BrF2N3
3-cyclopropyl-2-methylpyridin-4-amine 3-cyclopropyl-2-methylpyridin-4-amine 2806718-59-0 C9H12N2
3-bromo-6-cyclobutyl-2-(trifluoromethyl)pyridine 3-bromo-6-cyclobutyl-2-(trifluoromethyl)pyridine 2891520-41-3 C10H9BrF3N
3-bromo-6-(tetrahydrofuran-3-yl)-2-(trifluoromethyl)pyridine 3-bromo-6-(tetrahydrofuran-3-yl)-2-(trifluoromethyl)pyridine 2891519-88-1 C10H9BrF3NO
6-bromo-3-ethyl-2-(trifluoromethyl)pyridine 6-bromo-3-ethyl-2-(trifluoromethyl)pyridine 2891518-90-2 C8H7BrF3N
6-bromo-3-(tetrahydrofuran-2-yl)-2-(trifluoromethyl)pyridine 6-bromo-3-(tetrahydrofuran-2-yl)-2-(trifluoromethyl)pyridine 2891511-90-1 C10H9BrF3NO
5-bromo-2-ethylpyridin-4-ol 5-bromo-2-ethylpyridin-4-ol 2891519-97-2 C7H8BrNO
5-bromo-2-(tetrahydro-2H-pyran-3-yl)pyridin-4-amine 5-bromo-2-(tetrahydro-2H-pyran-3-yl)pyridin-4-amine 2891511-82-1 C10H13BrN2O
tert-butyl 6-bromo-5-phenyl-2,3-dihydro-4H-1,4-oxazine-4-carboxylate tert-butyl 6-bromo-5-phenyl-2,3-dihydro-4H-1,4-oxazine-4-carboxylate 2891521-17-6 C15H18BrNO3
tert-butyl 6-bromo-5-(furan-3-yl)-2,3-dihydro-4H-1,4-oxazine-4-carboxylate tert-butyl 6-bromo-5-(furan-3-yl)-2,3-dihydro-4H-1,4-oxazine-4-carboxylate 2891518-98-0 C13H16BrNO4
4-bromo-2-chloro-3-ethylpyridine 4-bromo-2-chloro-3-ethylpyridine 1256820-40-2 C7H7BrClN
tert-butyl 3-(5-aminopyridin-2-yl)morpholine-4-carboxylate tert-butyl 3-(5-aminopyridin-2-yl)morpholine-4-carboxylate 2891510-87-3 C14H21N3O3
tert-butyl 4-bromo-2H-1,2,3-triazole-2-carboxylate tert-butyl 4-bromo-2H-1,2,3-triazole-2-carboxylate 2891520-60-6 C7H10BrN3O2
4-iodo-2-isopropyl-5-(trifluoromethyl)pyridine 4-iodo-2-isopropyl-5-(trifluoromethyl)pyridine 2891518-24-2 C9H9F3IN
6-(4-bromo-1H-imidazol-1-yl)pyridin-3-amine 6-(4-bromo-1H-imidazol-1-yl)pyridin-3-amine 2952838-02-5 C8H7BrN4
4-bromo-5-cyclopropyl-2-(trifluoromethyl)pyridine 4-bromo-5-cyclopropyl-2-(trifluoromethyl)pyridine
2-bromo-4-isopropylpyridin-3-amine 2-bromo-4-isopropylpyridin-3-amine
2-bromo-3-cyclopropyl-4-methylpyridine 2-bromo-3-cyclopropyl-4-methylpyridine 2294949-67-8 C9H10BrN
6-methoxy-5-(tetrahydro-2H-pyran-3-yl)pyridin-3-amine 6-methoxy-5-(tetrahydro-2H-pyran-3-yl)pyridin-3-amine 2294950-02-8 C11H16N2O2
5-bromo-2-methoxy-3-(oxetan-3-yl)pyridine 5-bromo-2-methoxy-3-(oxetan-3-yl)pyridine 2294947-30-9 C9H10BrNO2
5-bromo-2-cyclohexyl-3-methoxypyridine 5-bromo-2-cyclohexyl-3-methoxypyridine 2294950-06-2 C12H16BrNO
3-(2,4-dibromo-1H-imidazol-1-yl)pyridazine 3-(2,4-dibromo-1H-imidazol-1-yl)pyridazine 2294950-30-2 C7H4Br2N4
5-bromo-1-(pyridin-2-yl)-1H-imidazol-2-amine 5-bromo-1-(pyridin-2-yl)-1H-imidazol-2-amine 2294944-31-1 C8H7BrN4
4-bromo-6,6'-difluoro-2,2'-bipyridine 4-bromo-6,6'-difluoro-2,2'-bipyridine 2294947-92-3 C10H5BrF2N2
3-(azetidin-1-yl)-4-bromopyridine 3-(azetidin-1-yl)-4-bromopyridine 2363781-08-0 C8H9BrN2
2-(azetidin-1-yl)-4-bromopyrimidine 2-(azetidin-1-yl)-4-bromopyrimidine 2363781-81-9 C7H8BrN3
1-ethyl-5-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole 1-ethyl-5-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole 2364586-23-0 C11H20BN3O3
2-(2-cyclopropylfuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-(2-cyclopropylfuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2364585-51-1 C13H19BO3
4-cyclobutyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-cyclobutyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2460672-29-9 C16H24BNO2
3-isopropyl-4-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-isopropyl-4-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2460671-36-5 C15H24BNO3
3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-2-yl)pyridine 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-2-yl)pyridine 2460672-17-5 C14H18BN3O2
4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)pyrimidine 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)pyrimidine 2460671-37-6 C14H17BN2O2S
4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidine 4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidine 2460672-58-4 C15H18BN3O2
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