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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
3-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-2-(methyl-d3)pyridine-4,5,6-d3 3-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-2-(methyl-d3)pyridine-4,5,6-d3 2256743-36-7 C9BrD8N3
2-(4-bromo-1H-imidazol-1-yl-2,5-d2)-6-(methyl-d3)pyridine-3,4,5-d3 2-(4-bromo-1H-imidazol-1-yl-2,5-d2)-6-(methyl-d3)pyridine-3,4,5-d3 2256743-50-5 C9BrD8N3
4-chloro-2-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyrimidine 4-chloro-2-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyrimidine 2256743-54-9 C8H2ClD5N4
5-bromo-2-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyrimidine 5-bromo-2-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyrimidine 2256743-69-6 C8H2BrD5N4
2-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyrimidin-5-amine 2-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyrimidin-5-amine 2256743-74-3 C8H4D5N5
4-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyrimidin-5,6-d2-2-amine 4-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyrimidin-5,6-d2-2-amine 2256743-96-9 C7H2BrD4N5
5-bromo-2-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyrimidine 5-bromo-2-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyrimidine 2256744-01-9 C7H2Br2D2N4
3-bromo-6-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridazine 3-bromo-6-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridazine 2256744-16-6 C8H2BrD5N4
6-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridazin-3-amine 6-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridazin-3-amine 2256744-21-3 C8H4D5N5
2-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridin-3-amine 2-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridin-3-amine 2256744-56-4 C9H5D5N4
6-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridin-2,4,5-d3-3-amine 6-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridin-2,4,5-d3-3-amine 2256744-61-1 C9H2D8N4
6-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridin-2,4,5-d3-3-amine 6-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridin-2,4,5-d3-3-amine 2256744-78-0 C9H2D8N4
2-bromo-3-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridine 2-bromo-3-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridine 2256744-83-7 C9H3BrD5N3
2-bromo-4-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridine 2-bromo-4-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridine 2256744-98-4 C9H3BrD5N3
3-bromo-4-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridine 3-bromo-4-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridine 2256745-03-4 C9H3BrD5N3
5-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridin-3-amine 5-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridin-3-amine 2256745-19-2 C8H5BrD2N4
5-bromo-2-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridine 5-bromo-2-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridine 2256745-24-9 C8H3Br2D2N3
3-bromo-4-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridine-2,5,6-d3 3-bromo-4-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridine-2,5,6-d3 2256745-39-6 C8Br2D5N3
2-bromo-4-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridine 2-bromo-4-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridine 2256745-44-3 C8H3Br2D2N3
5-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridin-2,4,6-d3-3-amine 5-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridin-2,4,6-d3-3-amine 2256745-60-3 C8H2BrD5N4
4-bromo-3-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridine 4-bromo-3-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridine 2256745-65-8 C9H3BrD5N3
5-bromo-2-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridine 5-bromo-2-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridine 2256745-81-8 C8H3Br2D2N3
2-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridin-3-amine 2-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridin-3-amine 2256745-86-3 C8H5BrD2N4
6-(1H-pyrazol-1-yl-d3)pyridazin-3-amine 6-(1H-pyrazol-1-yl-d3)pyridazin-3-amine 2256746-92-4 C7H4D3N5
2-bromo-4-(1H-imidazol-1-yl-d3)pyrimidine-5,6-d2 2-bromo-4-(1H-imidazol-1-yl-d3)pyrimidine-5,6-d2 2256747-09-6 C7BrD5N4
2-(1H-imidazol-1-yl-d3)pyrimidin-5,6-d2-4-amine 2-(1H-imidazol-1-yl-d3)pyrimidin-5,6-d2-4-amine 2256747-16-5 C7H2D5N5
2-fluoro-4-(4-methyl-1H-pyrazol-1-yl)pyridine 2-fluoro-4-(4-methyl-1H-pyrazol-1-yl)pyridine 1564835-25-1 C9H8FN3
2-fluoro-4-((tetrahydrofuran-3-yl)oxy)pyridine 2-fluoro-4-((tetrahydrofuran-3-yl)oxy)pyridine 1565507-58-5 C9H10FNO2
4-fluoro-2-(1H-pyrazol-1-yl)pyridine 4-fluoro-2-(1H-pyrazol-1-yl)pyridine 2256748-11-3 C8H6FN3
1-(6-fluoropyridin-2-yl)-1H-pyrazol-4-amine 1-(6-fluoropyridin-2-yl)-1H-pyrazol-4-amine 2256748-14-6 C8H7FN4
4-bromo-3-(oxetan-3-yloxy)pyridine 4-bromo-3-(oxetan-3-yloxy)pyridine 2363782-21-0 C8H8BrNO2
3-bromo-2-cyclopropylfuran 3-bromo-2-cyclopropylfuran 2363786-15-4 C7H7BrO
5-bromo-2-cyclobutyl-4-methylpyrimidine 5-bromo-2-cyclobutyl-4-methylpyrimidine 2460491-37-4 C9H11BrN2
5-bromo-4-methyl-2-(pyrrolidin-1-yl)pyrimidine 5-bromo-4-methyl-2-(pyrrolidin-1-yl)pyrimidine 1781826-19-4 C9H12BrN3
5-bromo-2-(1H-imidazol-1-yl)-4-methylpyrimidine 5-bromo-2-(1H-imidazol-1-yl)-4-methylpyrimidine 1935637-49-2
5-bromo-4-methyl-2-propoxypyrimidine 5-bromo-4-methyl-2-propoxypyrimidine 1935309-96-8 C8H11BrN2O
4-bromo-2-isopropyl-6-(trifluoromethyl)pyridine 4-bromo-2-isopropyl-6-(trifluoromethyl)pyridine 2460494-00-0 C9H9BrF3N
4-bromo-2-(sec-butyl)-6-(trifluoromethyl)pyridine 4-bromo-2-(sec-butyl)-6-(trifluoromethyl)pyridine 2460490-94-0 C10H11BrF3N
4-bromo-2-(tert-butyl)-6-(difluoromethyl)pyridine 4-bromo-2-(tert-butyl)-6-(difluoromethyl)pyridine 2460501-29-3 C10H12BrF2N
2-methyl-6-phenylpyridin-4-amine 2-methyl-6-phenylpyridin-4-amine 1807097-13-7 C12H12N2
2-(tert-butyl)-9-methyl-1,10-phenanthroline 2-(tert-butyl)-9-methyl-1,10-phenanthroline 156382-53-5 C17H18N2
4-bromo-2-(sec-butyl)-6-methylpyridine 4-bromo-2-(sec-butyl)-6-methylpyridine 2460500-84-7 C10H14BrN
2-(sec-butyl)-6-methylpyridin-4-ol 2-(sec-butyl)-6-methylpyridin-4-ol 2460492-82-2 C10H15NO
5-amino-3-isobutylpyridin-2(1H)-one 5-amino-3-isobutylpyridin-2(1H)-one 2460490-45-1 C9H14N2O
2-(5-bromo-4-chloropyrimidin-2-yl)thiazole 2-(5-bromo-4-chloropyrimidin-2-yl)thiazole 1565960-27-1
3-bromo-4-cyclohexyl-4H-1,2,4-triazole 3-bromo-4-cyclohexyl-4H-1,2,4-triazole 2460493-49-4 C8H12BrN3
3-bromo-4-(furan-2-yl)-4H-1,2,4-triazole 3-bromo-4-(furan-2-yl)-4H-1,2,4-triazole 2460491-63-6 C6H4BrN3O
3-bromo-4-(m-tolyl)-4H-1,2,4-triazole 3-bromo-4-(m-tolyl)-4H-1,2,4-triazole 2460492-18-4 C9H8BrN3
3-bromo-4-(2-fluorophenyl)-4H-1,2,4-triazole 3-bromo-4-(2-fluorophenyl)-4H-1,2,4-triazole 2460492-48-0 C8H5BrFN3
4-(4-chlorophenyl)-4H-1,2,4-triazol-3-amine 4-(4-chlorophenyl)-4H-1,2,4-triazol-3-amine 2460494-23-7 C8H7ClN4
4-(4-fluorophenyl)-4H-1,2,4-triazol-3-amine 4-(4-fluorophenyl)-4H-1,2,4-triazol-3-amine 2460491-77-2 C8H7FN4
5-methyl-4-propyl-4H-1,2,4-triazol-3-amine 5-methyl-4-propyl-4H-1,2,4-triazol-3-amine 1251258-70-4 C6H12N4
4-cyclopentyl-5-methyl-4H-1,2,4-triazol-3-amine 4-cyclopentyl-5-methyl-4H-1,2,4-triazol-3-amine 1249659-39-9 C8H14N4
3,5-dibromo-4-(oxetan-3-yl)-4H-1,2,4-triazole 3,5-dibromo-4-(oxetan-3-yl)-4H-1,2,4-triazole 2460494-35-1 C5H5Br2N3O
5-bromo-4-(p-tolyl)-1H-1,2,3-triazole 5-bromo-4-(p-tolyl)-1H-1,2,3-triazole 1204351-91-6 C9H8BrN3
5-bromo-4-(3-fluorophenyl)-1H-1,2,3-triazole 5-bromo-4-(3-fluorophenyl)-1H-1,2,3-triazole 1198612-89-3 C8H5BrFN3
3-(5-bromo-1H-1,2,3-triazol-4-yl)pyridine 3-(5-bromo-1H-1,2,3-triazol-4-yl)pyridine 1198612-91-7 C7H5BrN4
5-bromo-4-(2-chlorophenyl)-1H-1,2,3-triazole 5-bromo-4-(2-chlorophenyl)-1H-1,2,3-triazole 1990519-11-3 C8H5BrClN3
5-bromo-4-(4-bromophenyl)-1H-1,2,3-triazole 5-bromo-4-(4-bromophenyl)-1H-1,2,3-triazole 2386965-31-5 C8H5Br2N3
5-(furan-3-yl)-1H-1,2,3-triazole 5-(furan-3-yl)-1H-1,2,3-triazole 2460501-40-8 C6H5N3O
3-(4-(trifluoromethyl)phenyl)-4H-1,2,4-triazole 3-(4-(trifluoromethyl)phenyl)-4H-1,2,4-triazole 95728-16-8 C9H6F3N3
4-(4H-1,2,4-triazol-3-yl)thiazole 4-(4H-1,2,4-triazol-3-yl)thiazole 1253645-59-8 C5H4N4S
3-methyl-1-(pyrimidin-5-yl)-1H-pyrazol-4-amine 3-methyl-1-(pyrimidin-5-yl)-1H-pyrazol-4-amine 1374320-41-8 C8H9N5
4-(4-bromo-3-methyl-1H-pyrazol-1-yl)pyridine 4-(4-bromo-3-methyl-1H-pyrazol-1-yl)pyridine 2460492-13-9 C9H8BrN3
4-bromo-6-methyl-2-(pyridin-2-yl)pyrimidine 4-bromo-6-methyl-2-(pyridin-2-yl)pyrimidine 1188045-67-1 C10H8BrN3
3-bromo-2-methyl-6-(tetrahydro-2H-pyran-3-yl)pyridine 3-bromo-2-methyl-6-(tetrahydro-2H-pyran-3-yl)pyridine 2600400-15-3 C11H14BrNO
3-bromo-2-methyl-6-(thiophen-3-yl)pyridine 3-bromo-2-methyl-6-(thiophen-3-yl)pyridine 2600400-37-9 C10H8BrNS
2,8-dimethylimidazo[1,2-b]pyridazin-6-ol 2,8-dimethylimidazo[1,2-b]pyridazin-6-ol 2645416-64-2 C8H9N3O
4-bromo-2-cyclopropyl-6-methoxypyridine 4-bromo-2-cyclopropyl-6-methoxypyridine 2645419-56-1 C9H10BrNO
4-bromo-2-(methoxymethyl)-6-(trifluoromethyl)pyridine 4-bromo-2-(methoxymethyl)-6-(trifluoromethyl)pyridine 2645413-32-5 C8H7BrF3NO
2-bromo-4-(2,2-difluoro-1-methylcyclopropyl)pyridine 2-bromo-4-(2,2-difluoro-1-methylcyclopropyl)pyridine 2645419-59-4 C9H8BrF2N
4-bromo-1-(2,2-difluorocyclopropyl)-1H-1,2,3-triazole 4-bromo-1-(2,2-difluorocyclopropyl)-1H-1,2,3-triazole 2645419-18-5 C5H4BrF2N3
4-bromo-1-(4-fluorophenyl)-1H-1,2,3-triazole 4-bromo-1-(4-fluorophenyl)-1H-1,2,3-triazole 2256748-70-4 C8H5BrFN3
4-bromo-2-((1-methylazetidin-3-yl)oxy)pyrimidine 4-bromo-2-((1-methylazetidin-3-yl)oxy)pyrimidine 2645416-31-3 C8H10BrN3O
2-(azetidin-1-yl)-5-fluoropyridine 2-(azetidin-1-yl)-5-fluoropyridine 2645416-33-5 C8H9FN2
4-bromo-3-((tetrahydrofuran-2-yl)methoxy)pyridine 4-bromo-3-((tetrahydrofuran-2-yl)methoxy)pyridine 2090871-23-9 C10H12BrNO2
4-bromo-2-(2-methoxyethoxy)thiazole 4-bromo-2-(2-methoxyethoxy)thiazole 1289262-43-6 C6H8BrNO2S
2-(bicyclo[1.1.1]pentan-1-yl)-6-bromopyridine 2-(bicyclo[1.1.1]pentan-1-yl)-6-bromopyridine 2697156-61-7 C10H10BrN
1-(pyrimidin-5-yl)-1H-1,2,3-triazol-4-amine 1-(pyrimidin-5-yl)-1H-1,2,3-triazol-4-amine 1694456-11-5 C6H6N6
2-bromo-4-(3-methylbicyclo[1.1.1]pentan-1-yl)pyrimidine 2-bromo-4-(3-methylbicyclo[1.1.1]pentan-1-yl)pyrimidine 2697155-18-1 C10H11BrN2
4-bromo-2-(3-methylbicyclo[1.1.1]pentan-1-yl)-2H-1,2,3-triazole 4-bromo-2-(3-methylbicyclo[1.1.1]pentan-1-yl)-2H-1,2,3-triazole 2697162-36-8 C8H10BrN3
5-bromo-2-(pyrimidin-2-yl)oxazole 5-bromo-2-(pyrimidin-2-yl)oxazole 2697155-27-2 C7H4BrN3O
4-bromo-2-(pyridin-4-yl)oxazole 4-bromo-2-(pyridin-4-yl)oxazole 1402671-57-1 C8H5BrN2O
5-(4-bromo-1H-1,2,3-triazol-1-yl)-2-methylpyridine 5-(4-bromo-1H-1,2,3-triazol-1-yl)-2-methylpyridine 2256754-58-0 C8H7BrN4
4-bromo-1-(4-chlorophenyl)-1H-1,2,3-triazole 4-bromo-1-(4-chlorophenyl)-1H-1,2,3-triazole 2256754-63-7 C8H5BrClN3
2-(difluoromethyl)-5-methoxypyridin-3-amine 2-(difluoromethyl)-5-methoxypyridin-3-amine 1805256-41-0 C7H8F2N2O
tert-butyl 3-(4-bromo-6-(difluoromethyl)pyridin-2-yl)piperidine-1-carboxylate tert-butyl 3-(4-bromo-6-(difluoromethyl)pyridin-2-yl)piperidine-1-carboxylate 2768657-70-9 C16H21BrF2N2O2
5-bromo-8-isopropylquinoxaline 5-bromo-8-isopropylquinoxaline 2806720-63-6 C11H11BrN2
8-cyclopropylquinoxalin-5-amine 8-cyclopropylquinoxalin-5-amine 2806721-43-5 C11H11N3
tert-butyl 4-(6-bromopyridin-3-yl)-3-methylpiperidine-1-carboxylate tert-butyl 4-(6-bromopyridin-3-yl)-3-methylpiperidine-1-carboxylate 2806720-67-0 C16H23BrN2O2
tert-butyl 4-(6-chloropyridazin-3-yl)-3-methylpiperidine-1-carboxylate tert-butyl 4-(6-chloropyridazin-3-yl)-3-methylpiperidine-1-carboxylate 2806721-41-3 C15H22ClN3O2
2-(3-(tert-butyl)phenyl)morpholine 2-(3-(tert-butyl)phenyl)morpholine 2229234-68-6 C14H21NO
2-(4-bromopyrimidin-2-yl)tetrahydro-4H-pyran-4-one 2-(4-bromopyrimidin-2-yl)tetrahydro-4H-pyran-4-one 2806721-02-6 C9H9BrN2O2
2-(2-aminopyrimidin-4-yl)tetrahydro-4H-pyran-4-one 2-(2-aminopyrimidin-4-yl)tetrahydro-4H-pyran-4-one 2806720-10-3 C9H11N3O2
3-(6-aminopyridin-3-yl)tetrahydro-4H-pyran-4-one 3-(6-aminopyridin-3-yl)tetrahydro-4H-pyran-4-one 2806720-21-6 C10H12N2O2
3-(4-hydroxypyrimidin-2-yl)tetrahydro-4H-pyran-4-one 3-(4-hydroxypyrimidin-2-yl)tetrahydro-4H-pyran-4-one 2806719-15-1 C9H10N2O3
3-(2-aminopyrimidin-5-yl)tetrahydro-4H-pyran-4-one 3-(2-aminopyrimidin-5-yl)tetrahydro-4H-pyran-4-one 2806719-78-6 C9H11N3O2
3-(2-chloropyrimidin-4-yl)tetrahydro-4H-pyran-4-one 3-(2-chloropyrimidin-4-yl)tetrahydro-4H-pyran-4-one 2806721-27-5 C9H9ClN2O2
6-bromo-3-methyl-4H-chromeno[4,3-c]isoxazole 6-bromo-3-methyl-4H-chromeno[4,3-c]isoxazole 2821813-71-0 C11H8BrNO2
2-chloro-4-fluoropyrido[2,3-d]pyrimidine 2-chloro-4-fluoropyrido[2,3-d]pyrimidine 2891518-19-5 C7H3ClFN3
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