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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
pyrimidin-2(1H)-one-4,6-d2 pyrimidin-2(1H)-one-4,6-d2
pyrimidin-2,6-d2-4-amine pyrimidin-2,6-d2-4-amine
tert-butyl 4-oxo-3-(pyridin-4-yl)piperidine-1-carboxylate-2,2,3,5,5,6,6-d7 tert-butyl 4-oxo-3-(pyridin-4-yl)piperidine-1-carboxylate-2,2,3,5,5,6,6-d7
5-bromo-4-chloro-6-(methyl-d3)pyrimidine-2-d 5-bromo-4-chloro-6-(methyl-d3)pyrimidine-2-d 2363788-11-6 C5BrClD4N2
3-bromo-1H-pyrrolo[2,3-c]pyridine-2,4,5,7-d4 3-bromo-1H-pyrrolo[2,3-c]pyridine-2,4,5,7-d4
3H-imidazo[4,5-b]pyridine-2,5,6,7-d4 3H-imidazo[4,5-b]pyridine-2,5,6,7-d4
4,6-dichloro-2-(methyl-13C-d3)pyrimidine 4,6-dichloro-2-(methyl-13C-d3)pyrimidine
6-bromo-4-methylpyridin-2,5-d2-3-amine 6-bromo-4-methylpyridin-2,5-d2-3-amine
(1-(pyridin-4-yl-d4)piperidin-4-yl-2,2,3,3,4,5,5,6,6-d9)methan-d2-amine (1-(pyridin-4-yl-d4)piperidin-4-yl-2,2,3,3,4,5,5,6,6-d9)methan-d2-amine
6-(acetyl-d3)-2-amino-5-(methyl-d3)pyrido[2,3-d]pyrimidin-7(8H)-one-4-d 6-(acetyl-d3)-2-amino-5-(methyl-d3)pyrido[2,3-d]pyrimidin-7(8H)-one-4-d
5-bromo-1H-pyrrolo[2,3-b]pyridine-2,3,4,6-d4 5-bromo-1H-pyrrolo[2,3-b]pyridine-2,3,4,6-d4
4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2,3,4,4,6,6,7,7-d8 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2,3,4,4,6,6,7,7-d8
4-methyl-5-(2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-4-yl-3,5,6-d3)thiazol-2-amine 4-methyl-5-(2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-4-yl-3,5,6-d3)thiazol-2-amine
4-morpholinopyridin-2,5,6-d3-3-amine 4-morpholinopyridin-2,5,6-d3-3-amine
3-chloro-6-(trifluoromethyl)pyridazine-4,5-d2 3-chloro-6-(trifluoromethyl)pyridazine-4,5-d2
4-(piperidin-4-yl)pyridine-2,3,5,6-d4 4-(piperidin-4-yl)pyridine-2,3,5,6-d4
5-bromo-2-(pyridin-3-yl-d4)thiazole-4-d 5-bromo-2-(pyridin-3-yl-d4)thiazole-4-d
5-bromo-2-(tetrahydrofuran-3-yl-d7)pyridine 5-bromo-2-(tetrahydrofuran-3-yl-d7)pyridine
4-bromo-2-(tetrahydrofuran-3-yl)pyridine-3,5,6-d3 4-bromo-2-(tetrahydrofuran-3-yl)pyridine-3,5,6-d3
3-bromo-5-(thiophen-2-yl-d3)pyridine-2,4,6-d3 3-bromo-5-(thiophen-2-yl-d3)pyridine-2,4,6-d3
2-bromo-5-(1-(methyl-d3)pyrrolidin-2-yl-2,3,3,4,4,5,5-d7)pyridine-3,4,6-d3 2-bromo-5-(1-(methyl-d3)pyrrolidin-2-yl-2,3,3,4,4,5,5-d7)pyridine-3,4,6-d3
2-bromo-5-(1-(methyl-d3)pyrrolidin-2-yl-2,3,3,4,4,5,5-d7)pyridine 2-bromo-5-(1-(methyl-d3)pyrrolidin-2-yl-2,3,3,4,4,5,5-d7)pyridine
2-(methyl-d2)pyridine-6-d 2-(methyl-d2)pyridine-6-d 303769-78-0 C6H4D3N
2-bromo-3-fluoro-6-(methyl-d3)pyridine-4,5-d2 2-bromo-3-fluoro-6-(methyl-d3)pyridine-4,5-d2
2-chloro-4-fluoro-3-(methyl-d3)pyridine-5,6-d2 2-chloro-4-fluoro-3-(methyl-d3)pyridine-5,6-d2
4-chloro-5-(methyl-d3)-2-(trifluoromethyl)pyridine 4-chloro-5-(methyl-d3)-2-(trifluoromethyl)pyridine
4-fluoro-3-iodo-2-(methyl-d3)pyridine-5,6-d2 4-fluoro-3-iodo-2-(methyl-d3)pyridine-5,6-d2
4-bromo-2-(3-(methyl-d3)-1H-pyrazol-1-yl-4,5-d2)pyridine-3,5,6-d3 4-bromo-2-(3-(methyl-d3)-1H-pyrazol-1-yl-4,5-d2)pyridine-3,5,6-d3 2256742-46-6 C9BrD8N3
4-bromo-2-(3-(methyl-d3)-1H-pyrazol-1-yl-4,5-d2)pyrimidine-5,6-d2 4-bromo-2-(3-(methyl-d3)-1H-pyrazol-1-yl-4,5-d2)pyrimidine-5,6-d2 2256742-62-6 C8BrD7N4
4-bromo-3-(3-bromo-1H-pyrazol-1-yl-4,5-d2)pyridine-2,5,6-d3 4-bromo-3-(3-bromo-1H-pyrazol-1-yl-4,5-d2)pyridine-2,5,6-d3 2256742-82-0 C8Br2D5N3
2-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-3-(methyl-d3)pyridine-4,5,6-d3 2-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-3-(methyl-d3)pyridine-4,5,6-d3 2256743-43-6 C9BrD8N3
5-(4-bromo-1H-imidazol-1-yl-2,5-d2)-2-(methyl-d3)pyridine-3,4,6-d3 5-(4-bromo-1H-imidazol-1-yl-2,5-d2)-2-(methyl-d3)pyridine-3,4,6-d3 2256743-47-0 C9BrD8N3
4-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyrimidin-5,6-d2-2-amine 4-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyrimidin-5,6-d2-2-amine 2256743-61-8 C8H2D7N5
4-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyrimidin-2-amine 4-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyrimidin-2-amine 2256743-66-3 C8H4D5N5
2-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-4-chloropyrimidine 2-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-4-chloropyrimidine 2256743-81-2 C7H2BrClD2N4
2-bromo-4-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyrimidine 2-bromo-4-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyrimidine 2256743-85-6 C7H2Br2D2N4
6-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridazin-4,5-d2-3-amine 6-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridazin-4,5-d2-3-amine 2256744-08-6 C7H2BrD4N5
6-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridazin-3-amine 6-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridazin-3-amine 2256744-13-3 C7H4BrD2N5
1-(6-(methyl-d3)pyridazin-3-yl)-1H-pyrazol-3,5-d2-4-amine 1-(6-(methyl-d3)pyridazin-3-yl)-1H-pyrazol-3,5-d2-4-amine 2256744-29-1 C8H4D5N5
2-bromo-6-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridine 2-bromo-6-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridine 2256744-53-1 C9H3BrD5N3
5-bromo-2-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridine 5-bromo-2-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridine 2256744-69-9 C9H3BrD5N3
4-bromo-2-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridine-3,5,6-d3 4-bromo-2-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridine-3,5,6-d3 2256744-75-7 C9BrD8N3
2-bromo-3-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridine-4,5,6-d3 2-bromo-3-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridine-4,5,6-d3 2256744-90-6 C9BrD8N3
5-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridin-2,4,6-d3-3-amine 5-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)pyridin-2,4,6-d3-3-amine 2256744-95-1 C9H2D8N4
5-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridin-2,4,6-d3-3-amine 5-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridin-2,4,6-d3-3-amine 2256745-11-4 C8H2BrD5N4
4-bromo-3-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridine 4-bromo-3-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridine 2256745-16-9 C8H3Br2D2N3
2-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridin-3,5,6-d3-4-amine 2-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridin-3,5,6-d3-4-amine 2256745-31-8 C8H2BrD5N4
3-bromo-2-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridine-4,5,6-d3 3-bromo-2-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridine-4,5,6-d3 2256745-36-3 C8Br2D5N3
5-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridin-3-amine 5-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridin-3-amine 2256745-52-3 C8H5BrD2N4
4-bromo-3-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridine-2,5,6-d3 4-bromo-3-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridine-2,5,6-d3 2256745-57-8 C8Br2D5N3
3-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridin-4,5,6-d3-2-amine 3-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridin-4,5,6-d3-2-amine 2256745-72-7 C9H2D8N4
5-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridin-3,4,6-d3-2-amine 5-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridin-3,4,6-d3-2-amine 2256745-78-3 C9H2D8N4
2-bromo-6-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridine 2-bromo-6-(4-bromo-1H-imidazol-1-yl-2,5-d2)pyridine 2256745-83-0 C8H3Br2D2N3
3-bromo-6-(1H-imidazol-1-yl-d3)pyridazine-4,5-d2 3-bromo-6-(1H-imidazol-1-yl-d3)pyridazine-4,5-d2 2256746-89-9 C7BrD5N4
2-(1H-pyrazol-1-yl-d3)pyrimidin-5-amine 2-(1H-pyrazol-1-yl-d3)pyrimidin-5-amine 2256747-04-1 C7H4D3N5
4-bromo-2-(1H-imidazol-1-yl-d3)pyrimidine 4-bromo-2-(1H-imidazol-1-yl-d3)pyrimidine 2256747-13-2 C7H2BrD3N4
2-fluoro-4-(4-methyl-1H-imidazol-1-yl)pyridine 2-fluoro-4-(4-methyl-1H-imidazol-1-yl)pyridine 2256747-97-2 C9H8FN3
2-fluoro-4-(1H-pyrazol-1-yl)pyridine 2-fluoro-4-(1H-pyrazol-1-yl)pyridine 1565015-52-2 C8H6FN3
2-(4-bromo-2-(trifluoromethyl)phenyl)tetrahydrofuran 2-(4-bromo-2-(trifluoromethyl)phenyl)tetrahydrofuran 2256748-06-6 C11H10BrF3O
4-bromo-5-methoxy-1-methyl-1H-1,2,3-triazole 4-bromo-5-methoxy-1-methyl-1H-1,2,3-triazole 2363787-64-6 C4H6BrN3O
4-(oxetan-3-yloxy)pyrimidin-2-amine 4-(oxetan-3-yloxy)pyrimidin-2-amine 1598264-05-1 C7H9N3O2
5-bromo-2-(oxetan-3-yloxy)thiazole 5-bromo-2-(oxetan-3-yloxy)thiazole 2363787-30-6 C6H6BrNO2S
5-bromo-2-(sec-butyl)-4-methylpyrimidine 5-bromo-2-(sec-butyl)-4-methylpyrimidine 2460491-56-7 C9H13BrN2
5-bromo-4-methyl-2-(4-methylpiperidin-1-yl)pyrimidine 5-bromo-4-methyl-2-(4-methylpiperidin-1-yl)pyrimidine 1780428-39-8
5-bromo-4-methyl-2-(3-methyl-1H-pyrazol-1-yl)pyrimidine 5-bromo-4-methyl-2-(3-methyl-1H-pyrazol-1-yl)pyrimidine 1934789-80-6
2-(2-bromo-1H-imidazol-1-yl)pyridine 2-(2-bromo-1H-imidazol-1-yl)pyridine 1505359-38-5 C8H6BrN3
5-(2-bromo-1H-imidazol-1-yl)pyrimidine 5-(2-bromo-1H-imidazol-1-yl)pyrimidine 2460500-68-7 C7H5BrN4
2-ethyl-6-(trifluoromethyl)pyridin-4-amine 2-ethyl-6-(trifluoromethyl)pyridin-4-amine 2460491-24-9 C8H9F3N2
4-bromo-2-ethyl-6-(trifluoromethyl)pyridine 4-bromo-2-ethyl-6-(trifluoromethyl)pyridine 2385874-32-6 C8H7BrF3N
4-chloro-2-cyclobutyl-6-(trifluoromethyl)pyridine 4-chloro-2-cyclobutyl-6-(trifluoromethyl)pyridine 2460500-81-4 C10H9ClF3N
4-bromo-2-(sec-butyl)-6-(difluoromethyl)pyridine 4-bromo-2-(sec-butyl)-6-(difluoromethyl)pyridine 2460500-36-9 C10H12BrF2N
3-bromo-6-(1H-imidazol-2-yl)pyridazine 3-bromo-6-(1H-imidazol-2-yl)pyridazine 2256748-32-8 C7H5BrN4
4-(tert-butyl)-6-methylpyridin-2(1H)-one 4-(tert-butyl)-6-methylpyridin-2(1H)-one 1512954-44-7 C10H15NO
5-amino-3-propylpyridin-2(1H)-one 5-amino-3-propylpyridin-2(1H)-one 2460494-40-8 C8H12N2O
5-bromo-4-chloro-2-isobutylpyrimidine 5-bromo-4-chloro-2-isobutylpyrimidine 1509494-36-3 C8H10BrClN2
5-(5-bromo-4-chloropyrimidin-2-yl)thiazole 5-(5-bromo-4-chloropyrimidin-2-yl)thiazole 1516735-59-3
5-(4-bromo-2-fluoro-1H-imidazol-1-yl)pyrimidine 5-(4-bromo-2-fluoro-1H-imidazol-1-yl)pyrimidine 2460500-82-5 C7H4BrFN4
3-bromo-4-cyclopentyl-4H-1,2,4-triazole 3-bromo-4-cyclopentyl-4H-1,2,4-triazole 2460490-07-5 C7H10BrN3
4-(3-bromo-4H-1,2,4-triazol-4-yl)thiazole 4-(3-bromo-4H-1,2,4-triazol-4-yl)thiazole 2460492-14-0 C5H3BrN4S
3-bromo-4-(2-methoxyphenyl)-4H-1,2,4-triazole 3-bromo-4-(2-methoxyphenyl)-4H-1,2,4-triazole 2460494-58-8 C9H8BrN3O
4-(p-tolyl)-4H-1,2,4-triazol-3-amine 4-(p-tolyl)-4H-1,2,4-triazol-3-amine 107733-42-6 C9H10N4
4-cyclohexyl-4H-1,2,4-triazol-3-amine 4-cyclohexyl-4H-1,2,4-triazol-3-amine 1248293-50-6 C8H14N4
4-isobutyl-5-methyl-4H-1,2,4-triazol-3-amine 4-isobutyl-5-methyl-4H-1,2,4-triazol-3-amine 2460500-98-3 C7H14N4
3,5-dibromo-4-(sec-butyl)-4H-1,2,4-triazole 3,5-dibromo-4-(sec-butyl)-4H-1,2,4-triazole 2460493-65-4 C6H9Br2N3
3,5-dibromo-4-cyclohexyl-4H-1,2,4-triazole 3,5-dibromo-4-cyclohexyl-4H-1,2,4-triazole 2460500-38-1 C8H11Br2N3
3-bromo-5-(furan-3-yl)-4H-1,2,4-triazole 3-bromo-5-(furan-3-yl)-4H-1,2,4-triazole 2460501-39-5 C6H4BrN3O
5-bromo-4-(3-methoxyphenyl)-1H-1,2,3-triazole 5-bromo-4-(3-methoxyphenyl)-1H-1,2,3-triazole 2460493-67-6 C9H8BrN3O
5-bromo-4-(sec-butyl)-1H-1,2,3-triazole 5-bromo-4-(sec-butyl)-1H-1,2,3-triazole 2460493-71-2 C6H10BrN3
2-(5-bromo-1H-1,2,3-triazol-4-yl)benzonitrile 2-(5-bromo-1H-1,2,3-triazol-4-yl)benzonitrile 2460490-34-8 C9H5BrN4
4-(tetrahydrofuran-3-yl)-1H-1,2,3-triazole 4-(tetrahydrofuran-3-yl)-1H-1,2,3-triazole 2460493-73-4 C6H9N3O
4-bromo-5-ethyl-1-isopropyl-1H-1,2,3-triazole 4-bromo-5-ethyl-1-isopropyl-1H-1,2,3-triazole 2460493-80-3 C7H12BrN3
3-(2-methoxyphenyl)-4H-1,2,4-triazole 3-(2-methoxyphenyl)-4H-1,2,4-triazole 50616-34-7 C9H9N3O
4-(2-bromopyridin-4-yl)pyrimidine 4-(2-bromopyridin-4-yl)pyrimidine 2460492-00-4 C9H6BrN3
2-(tetrahydrofuran-3-yl)thiazol-5-amine 2-(tetrahydrofuran-3-yl)thiazol-5-amine 2460500-61-0 C7H10N2OS
1-(5-bromopyridin-3-yl)azetidin-3-ol 1-(5-bromopyridin-3-yl)azetidin-3-ol 1864111-71-6 C8H9BrN2O
2-(5-bromo-6-fluoropyridin-2-yl)benzonitrile 2-(5-bromo-6-fluoropyridin-2-yl)benzonitrile 2600399-02-6 C12H6BrFN2
3-bromo-6-(4-bromophenyl)-2-fluoropyridine 3-bromo-6-(4-bromophenyl)-2-fluoropyridine 2600400-29-9 C11H6Br2FN
3-bromo-2-methyl-6-(tetrahydrofuran-3-yl)pyridine 3-bromo-2-methyl-6-(tetrahydrofuran-3-yl)pyridine 2600400-32-4 C10H12BrNO
2,4-dibromo-6-(oxetan-3-yl)pyridine 2,4-dibromo-6-(oxetan-3-yl)pyridine 2645411-88-5 C8H7Br2NO
4-bromo-2-(methoxymethyl)-6-(oxetan-3-yl)pyridine 4-bromo-2-(methoxymethyl)-6-(oxetan-3-yl)pyridine 2645419-16-3 C10H12BrNO2
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