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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-(1H-imidazol-1-yl-d3)pyrimidin-2-amine 4-(1H-imidazol-1-yl-d3)pyrimidin-2-amine 2256747-07-4 C7H4D3N5
4-bromo-2-(1H-imidazol-1-yl-d3)pyrimidine-5,6-d2 4-bromo-2-(1H-imidazol-1-yl-d3)pyrimidine-5,6-d2 2256747-15-4 C7BrD5N4
2-fluoro-4-(1H-imidazol-1-yl)pyridine 2-fluoro-4-(1H-imidazol-1-yl)pyridine 1564785-95-0 C8H6FN3
4-(cyclohexyloxy)-2-fluoropyridine 4-(cyclohexyloxy)-2-fluoropyridine 1564742-51-3 C11H14FNO
1-(1,3,5-triazin-2-yl)azetidin-3-ol 1-(1,3,5-triazin-2-yl)azetidin-3-ol 2363783-23-5 C6H8N4O
2-(4-bromo-1H-imidazol-1-yl)-4-fluoropyridine 2-(4-bromo-1H-imidazol-1-yl)-4-fluoropyridine 2256748-16-8 C8H5BrFN3
5-bromo-4-methyl-2-propylpyrimidine 5-bromo-4-methyl-2-propylpyrimidine 2460501-37-3 C8H11BrN2
5-bromo-N,N-diethyl-4-methylpyrimidin-2-amine 5-bromo-N,N-diethyl-4-methylpyrimidin-2-amine 1369131-52-1 C9H14BrN3
4-fluoro-2-(1H-imidazol-2-yl)pyridine 4-fluoro-2-(1H-imidazol-2-yl)pyridine 1221279-13-5 C8H6FN3
5-bromo-2-ethoxy-4-methylpyrimidine 5-bromo-2-ethoxy-4-methylpyrimidine 1888853-59-5 C7H9BrN2O
3-(2-bromo-1H-imidazol-1-yl)pyridazine 3-(2-bromo-1H-imidazol-1-yl)pyridazine 2274026-09-2 C7H7N5
2-(4-bromo-1H-imidazol-2-yl)-6-fluoropyridine 2-(4-bromo-1H-imidazol-2-yl)-6-fluoropyridine 2256748-24-8 C8H5BrFN3
2-(sec-butyl)-4-chloro-6-(trifluoromethyl)pyridine 2-(sec-butyl)-4-chloro-6-(trifluoromethyl)pyridine 2460501-24-8 C10H11ClF3N
4-bromo-2-cyclopropyl-6-(difluoromethyl)pyridine 4-bromo-2-cyclopropyl-6-(difluoromethyl)pyridine 2460494-59-9 C9H8BrF2N
2-isopropyl-1,10-phenanthroline 2-isopropyl-1,10-phenanthroline 869900-82-3 C15H14N2
2-isopropyl-9-methyl-1,10-phenanthroline 2-isopropyl-9-methyl-1,10-phenanthroline 2460501-33-9 C16H16N2
3-chloro-6-(1H-imidazol-2-yl)pyridazine 3-chloro-6-(1H-imidazol-2-yl)pyridazine 2256748-31-7 C7H5ClN4
6-bromo-5-(tert-butyl)pyridin-3-amine 6-bromo-5-(tert-butyl)pyridin-3-amine 2460494-56-6 C9H13BrN2
5-amino-3-cyclopropylpyridin-2(1H)-one 5-amino-3-cyclopropylpyridin-2(1H)-one 2460491-07-8 C8H10N2O
5-bromo-4-chloro-2,2'-bipyrimidine 5-bromo-4-chloro-2,2'-bipyrimidine 1543250-32-3 C8H4BrClN4
3-bromo-4-(tetrahydrofuran-2-yl)-4H-1,2,4-triazole 3-bromo-4-(tetrahydrofuran-2-yl)-4H-1,2,4-triazole 2460491-50-1 C6H8BrN3O
3-bromo-4-(o-tolyl)-4H-1,2,4-triazole 3-bromo-4-(o-tolyl)-4H-1,2,4-triazole 2460491-57-8 C9H8BrN3
4-(3-chlorophenyl)-4H-1,2,4-triazol-3-amine 4-(3-chlorophenyl)-4H-1,2,4-triazol-3-amine 2460494-61-3 C8H7ClN4
4-(4-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-amine 4-(4-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-amine 2460491-64-7 C9H7F3N4
4-isopropyl-5-methyl-4H-1,2,4-triazol-3-amine 4-isopropyl-5-methyl-4H-1,2,4-triazol-3-amine 1248632-39-4
5-methyl-4-(oxetan-3-yl)-4H-1,2,4-triazol-3-amine 5-methyl-4-(oxetan-3-yl)-4H-1,2,4-triazol-3-amine 2460492-40-2 C6H10N4O
3,5-dibromo-4-cyclobutyl-4H-1,2,4-triazole 3,5-dibromo-4-cyclobutyl-4H-1,2,4-triazole 2460492-45-7 C6H7Br2N3
3-bromo-5-(o-tolyl)-4H-1,2,4-triazole 3-bromo-5-(o-tolyl)-4H-1,2,4-triazole 1785591-77-6 C9H8BrN3
5-bromo-4-(m-tolyl)-1H-1,2,3-triazole 5-bromo-4-(m-tolyl)-1H-1,2,3-triazole 2460492-05-9 C9H8BrN3
5-bromo-4-(2-fluorophenyl)-1H-1,2,3-triazole 5-bromo-4-(2-fluorophenyl)-1H-1,2,3-triazole 2460490-17-7 C8H5BrFN3
5-bromo-4-cyclopentyl-1H-1,2,3-triazole 5-bromo-4-cyclopentyl-1H-1,2,3-triazole 2460490-19-9 C7H10BrN3
4-(5-bromo-1H-1,2,3-triazol-4-yl)benzonitrile 4-(5-bromo-1H-1,2,3-triazol-4-yl)benzonitrile 2460500-32-5 C9H5BrN4
4-bromo-1-ethyl-5-isopropyl-1H-1,2,3-triazole 4-bromo-1-ethyl-5-isopropyl-1H-1,2,3-triazole 2460501-17-9 C7H12BrN3
3-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazole 3-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazole 2460493-84-7 C9H6F3N3
4-(5-bromofuran-2-yl)pyrimidine 4-(5-bromofuran-2-yl)pyrimidine 2460492-12-8 C8H5BrN2O
3-methyl-1-(pyrimidin-2-yl)-1H-pyrazol-4-amine 3-methyl-1-(pyrimidin-2-yl)-1H-pyrazol-4-amine 1393100-64-5 C8H9N5
1-(6-bromopyridin-2-yl)azetidin-3-ol 1-(6-bromopyridin-2-yl)azetidin-3-ol 1850413-06-7 C8H9BrN2O
1-(5-bromothiophen-2-yl)azetidin-3-ol 1-(5-bromothiophen-2-yl)azetidin-3-ol 2600400-31-3 C7H8BrNOS
3-bromo-2-fluoro-6-(furan-3-yl)pyridine 3-bromo-2-fluoro-6-(furan-3-yl)pyridine 2600398-75-0 C9H5BrFNO
3-bromo-2-methyl-6-(tetrahydro-2H-pyran-4-yl)pyridine 3-bromo-2-methyl-6-(tetrahydro-2H-pyran-4-yl)pyridine 2600398-78-3 C11H14BrNO
3-bromo-6-(furan-2-yl)-2-methylpyridine 3-bromo-6-(furan-2-yl)-2-methylpyridine 1256816-63-3 C10H8BrNO
1-(4-bromo-6-cyclopropylpyridin-2-yl)ethan-1-one 1-(4-bromo-6-cyclopropylpyridin-2-yl)ethan-1-one 2645416-19-7 C10H10BrNO
4-bromo-2-fluoro-6-(methoxymethyl)pyridine 4-bromo-2-fluoro-6-(methoxymethyl)pyridine 2645412-39-9 C7H7BrFNO
2-bromo-6-(2,2-difluoro-1-methylcyclopropyl)pyridine 2-bromo-6-(2,2-difluoro-1-methylcyclopropyl)pyridine 2645419-81-2 C9H8BrF2N
4-bromo-2-((1-methylazetidin-3-yl)oxy)pyridine 4-bromo-2-((1-methylazetidin-3-yl)oxy)pyridine 2645416-17-5 C9H11BrN2O
2-(azetidin-3-yloxy)-4-bromopyridine 2-(azetidin-3-yloxy)-4-bromopyridine 2645413-37-0 C8H9BrN2O
4-bromo-3-(oxetan-2-ylmethoxy)pyridine 4-bromo-3-(oxetan-2-ylmethoxy)pyridine 1628707-40-3 C9H10BrNO2
4-bromo-1-(thiophen-3-yl)-1H-1,2,3-triazole 4-bromo-1-(thiophen-3-yl)-1H-1,2,3-triazole 2256748-81-7 C6H4BrN3S
4-(4-bromo-1H-1,2,3-triazol-1-yl)pyrimidine 4-(4-bromo-1H-1,2,3-triazol-1-yl)pyrimidine 2256754-40-0 C6H4BrN5
2-(bicyclo[1.1.1]pentan-1-yl)-4-bromo-2H-1,2,3-triazole 2-(bicyclo[1.1.1]pentan-1-yl)-4-bromo-2H-1,2,3-triazole 2697162-31-3 C7H8BrN3
5-bromo-2-(pyrimidin-4-yl)oxazole 5-bromo-2-(pyrimidin-4-yl)oxazole 2697155-17-0 C7H4BrN3O
4-bromo-2-(pyridin-3-yl)oxazole 4-bromo-2-(pyridin-3-yl)oxazole 1402667-03-1 C8H5BrN2O
2-(4-bromo-1H-1,2,3-triazol-1-yl)-6-chloropyridine 2-(4-bromo-1H-1,2,3-triazol-1-yl)-6-chloropyridine 2256754-57-9 C7H4BrClN4
4-bromo-1-(3-chlorophenyl)-1H-1,2,3-triazole 4-bromo-1-(3-chlorophenyl)-1H-1,2,3-triazole 2256754-62-6 C8H5BrClN3
5-bromo-1-cyclopentyl-1H-1,2,3-triazole 5-bromo-1-cyclopentyl-1H-1,2,3-triazole 1897511-45-3 C7H10BrN3
5-bromo-2-cyclopropyl-4-methoxythiazole 5-bromo-2-cyclopropyl-4-methoxythiazole 2768654-46-0 C7H8BrNOS
8-ethylquinoxalin-5-amine 8-ethylquinoxalin-5-amine 2806720-84-1 C10H11N3
tert-butyl 4-(2-bromopyridin-4-yl)-3-methylpiperidine-1-carboxylate tert-butyl 4-(2-bromopyridin-4-yl)-3-methylpiperidine-1-carboxylate 2806719-49-1 C16H23BrN2O2
tert-butyl 4-(5-bromopyridin-2-yl)-3-methylpiperidine-1-carboxylate tert-butyl 4-(5-bromopyridin-2-yl)-3-methylpiperidine-1-carboxylate 2806719-99-1 C16H23BrN2O2
tert-butyl 4-(6-bromopyridazin-3-yl)-3-methylpiperidine-1-carboxylate tert-butyl 4-(6-bromopyridazin-3-yl)-3-methylpiperidine-1-carboxylate 2806720-93-2 C15H22BrN3O2
3-(pyridin-2-yl)piperidin-4-one 3-(pyridin-2-yl)piperidin-4-one 1367950-24-0 C10H12N2O
2-(6-bromopyridin-3-yl)tetrahydro-4H-pyran-4-one 2-(6-bromopyridin-3-yl)tetrahydro-4H-pyran-4-one 2357485-24-4 C10H10BrNO2
2-(2-hydroxypyrimidin-4-yl)tetrahydro-4H-pyran-4-one 2-(2-hydroxypyrimidin-4-yl)tetrahydro-4H-pyran-4-one 2806720-91-0 C9H10N2O3
3-(5-aminopyridin-3-yl)tetrahydro-4H-pyran-4-one 3-(5-aminopyridin-3-yl)tetrahydro-4H-pyran-4-one 2806721-08-2 C10H12N2O2
3-(5-hydroxypyrimidin-2-yl)tetrahydro-4H-pyran-4-one 3-(5-hydroxypyrimidin-2-yl)tetrahydro-4H-pyran-4-one 2806718-77-2 C9H10N2O3
3-(2-hydroxypyrimidin-5-yl)tetrahydro-4H-pyran-4-one 3-(2-hydroxypyrimidin-5-yl)tetrahydro-4H-pyran-4-one 2806720-24-9 C9H10N2O3
3-(4-bromopyrimidin-2-yl)tetrahydro-4H-pyran-4-one 3-(4-bromopyrimidin-2-yl)tetrahydro-4H-pyran-4-one 2806729-36-0 C9H9BrN2O2
3-(6-bromopyridazin-3-yl)tetrahydro-4H-pyran-4-one 3-(6-bromopyridazin-3-yl)tetrahydro-4H-pyran-4-one 2806728-69-6 C9H9BrN2O2
4-bromo-1-(pyridin-4-yl)-1H-imidazol-2-amine 4-bromo-1-(pyridin-4-yl)-1H-imidazol-2-amine 2294949-06-5 C8H7BrN4
3-methyl-4H-chromeno[4,3-c]isoxazol-6-amine 3-methyl-4H-chromeno[4,3-c]isoxazol-6-amine 2821813-67-4 C11H10N2O2
3-bromo-6-ethyl-2-(trifluoromethyl)pyridine 3-bromo-6-ethyl-2-(trifluoromethyl)pyridine 1211517-92-8 C8H7BrF3N
3-bromo-6-(tetrahydro-2H-pyran-2-yl)-2-(trifluoromethyl)pyridine 3-bromo-6-(tetrahydro-2H-pyran-2-yl)-2-(trifluoromethyl)pyridine 2891518-95-7 C11H11BrF3NO
3-bromo-6-(1,4-dioxan-2-yl)-2-(trifluoromethyl)pyridine 3-bromo-6-(1,4-dioxan-2-yl)-2-(trifluoromethyl)pyridine 2891511-88-7 C10H9BrF3NO2
2-(6-bromo-2-(trifluoromethyl)pyridin-3-yl)morpholine 2-(6-bromo-2-(trifluoromethyl)pyridin-3-yl)morpholine 2891511-30-9 C10H10BrF3N2O
5-bromo-2-cyclopropylpyridin-4-ol 5-bromo-2-cyclopropylpyridin-4-ol 2891521-15-4 C8H8BrNO
5-isopropyl-2-methylpyridin-4-amine 5-isopropyl-2-methylpyridin-4-amine 2891510-77-1 C9H14N2
tert-butyl 6-iodo-5-methyl-2,3-dihydro-4H-1,4-oxazine-4-carboxylate tert-butyl 6-iodo-5-methyl-2,3-dihydro-4H-1,4-oxazine-4-carboxylate 2891518-25-3 C10H16INO3
4-bromo-1-(pyridazin-3-yl)-1H-imidazol-2-amine 4-bromo-1-(pyridazin-3-yl)-1H-imidazol-2-amine 2294957-55-2 C7H6BrN5
tert-butyl 3,5-dicyclopropyl-4H-1,4-oxazine-4-carboxylate tert-butyl 3,5-dicyclopropyl-4H-1,4-oxazine-4-carboxylate 2891520-30-0 C15H21NO3
tert-butyl 3-(6-aminopyridin-3-yl)morpholine-4-carboxylate tert-butyl 3-(6-aminopyridin-3-yl)morpholine-4-carboxylate 2385650-37-1 C14H21N3O3
tert-butyl 3-(6-aminopyrimidin-4-yl)morpholine-4-carboxylate tert-butyl 3-(6-aminopyrimidin-4-yl)morpholine-4-carboxylate 2891521-18-7 C13H20N4O3
5,5'-difluoro-4,4'-dimethyl-2,2'-bipyridine 5,5'-difluoro-4,4'-dimethyl-2,2'-bipyridine 2260917-42-6 C12H10F2N2
2-bromo-4-cyclopropyl-5-(trifluoromethyl)pyridine 2-bromo-4-cyclopropyl-5-(trifluoromethyl)pyridine 2891520-62-8 C9H7BrF3N
2-chloro-6-ethyl-4-fluoropyridine 2-chloro-6-ethyl-4-fluoropyridine 2952838-00-3 C7H7ClFN
5-bromo-2-methoxy-3-(tetrahydro-2H-pyran-2-yl)pyridine 5-bromo-2-methoxy-3-(tetrahydro-2H-pyran-2-yl)pyridine 2294949-74-7 C11H14BrNO2
6-methoxy-5-(tetrahydro-2H-pyran-4-yl)pyridin-3-amine 6-methoxy-5-(tetrahydro-2H-pyran-4-yl)pyridin-3-amine 2294945-31-4 C11H16N2O2
5-methoxy-6-(tetrahydrofuran-2-yl)pyridin-3-amine 5-methoxy-6-(tetrahydrofuran-2-yl)pyridin-3-amine 2294949-99-6 C10H14N2O2
5-bromo-3-methoxy-2-(tetrahydro-2H-pyran-4-yl)pyridine 5-bromo-3-methoxy-2-(tetrahydro-2H-pyran-4-yl)pyridine 2294945-36-9 C11H14BrNO2
4-(2,5-dibromo-1H-imidazol-1-yl)pyridine 4-(2,5-dibromo-1H-imidazol-1-yl)pyridine 2294947-39-8 C8H5Br2N3
4-fluoro-5,6-dimethylpyridin-3-amine 4-fluoro-5,6-dimethylpyridin-3-amine 2294945-76-7 C7H9FN2
3-bromo-2-cyclobutylthiophene 3-bromo-2-cyclobutylthiophene 2363779-38-6 C8H9BrS
5-fluoro-1-(tetrahydrofuran-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole 5-fluoro-1-(tetrahydrofuran-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole 2364572-98-3 C12H19BFN3O3
3-(oxetan-3-yloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(oxetan-3-yloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2364586-46-7 C14H20BNO4
5-methyl-2-(oxetan-3-yloxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 5-methyl-2-(oxetan-3-yloxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2364586-14-9 C13H20BNO4S
2-(sec-butyl)-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(sec-butyl)-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2460671-66-1 C16H26BNO2
1-ethyl-5-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole 1-ethyl-5-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazole 2460671-71-8 C13H24BN3O2
4-(3-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine 4-(3-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine 2460672-81-3 C19H23BN2O2
4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)pyridine 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)pyridine 2710289-79-3 C12H14BF4NO2
3-(6-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)benzonitrile 3-(6-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)benzonitrile 2710289-87-3 C18H18BFN2O2
(2-methyl-6-(tetrahydrofuran-3-yl)pyridin-3-yl)boronic acid (2-methyl-6-(tetrahydrofuran-3-yl)pyridin-3-yl)boronic acid 2710290-22-3 C10H14BNO3
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