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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
8-(methyl-d3)imidazo[1,2-b]pyridazin-2,3,7-d3-6-amine 8-(methyl-d3)imidazo[1,2-b]pyridazin-2,3,7-d3-6-amine 2645417-14-5 C7H2D6N4
6-aminopyridin-2,4,5-d3-3-ol 6-aminopyridin-2,4,5-d3-3-ol 2645417-15-6 C5H3D3N2O
4-bromo-6-(methyl-d3)pyridin-3-amine 4-bromo-6-(methyl-d3)pyridin-3-amine 2645419-95-8 C6H4BrD3N2
3-bromo-2-(methyl-d3)pyridine-4,5,6-d3 3-bromo-2-(methyl-d3)pyridine-4,5,6-d3 2645416-07-3 C6BrD6N
4-bromo-6-(methyl-13C-d3)pyrimidine 4-bromo-6-(methyl-13C-d3)pyrimidine 2645417-39-4 C5H2BrD3N2
6-bromo-1-(ethyl-d5)pyridin-2(1H)-one-3,4,5-d3 6-bromo-1-(ethyl-d5)pyridin-2(1H)-one-3,4,5-d3 2645412-92-4 C7BrD8NO
2-chloro-5-hydroxy-3-(methyl-d3)pyrimidin-4(3H)-one 2-chloro-5-hydroxy-3-(methyl-d3)pyrimidin-4(3H)-one 2645413-18-7 C5H2ClD3N2O2
3-(methyl-d3)-2-(trifluoromethyl)pyridin-5,6-d2-4-amine 3-(methyl-d3)-2-(trifluoromethyl)pyridin-5,6-d2-4-amine 2645419-33-4 C7H2D5F3N2
2,3,5-tris(methyl-d3)pyridin-6-d-4-amine 2,3,5-tris(methyl-d3)pyridin-6-d-4-amine 2645414-08-8 C8H2D10N2
4-bromo-6-(methyl-d3)pyrimidine-2,5-d2 4-bromo-6-(methyl-d3)pyrimidine-2,5-d2 2241865-95-0 C5BrD5N2
2-bromo-6-((1-(methyl-d3)azetidin-3-yl-2,2,3,4,4-d5)oxy)pyridine 2-bromo-6-((1-(methyl-d3)azetidin-3-yl-2,2,3,4,4-d5)oxy)pyridine 2645412-25-3 C9H3BrD8N2O
4-bromo-2-((1-(methyl-d3)azetidin-3-yl-2,2,3,4,4-d5)oxy)pyridine-3,5,6-d3 4-bromo-2-((1-(methyl-d3)azetidin-3-yl-2,2,3,4,4-d5)oxy)pyridine-3,5,6-d3 2645418-55-7 C9BrD11N2O
3-bromo-7-methylpyrido[2,3-d]pyridazin-8(7H)-one-2,4,5-d3 3-bromo-7-methylpyrido[2,3-d]pyridazin-8(7H)-one-2,4,5-d3 2645414-01-1 C8H3BrD3N3O
4-bromopyridine-3,5-d2-2,6-diamine 4-bromopyridine-3,5-d2-2,6-diamine 2645416-72-2 C5H4BrD2N3
2-bromo-6-(2-(methoxy-d3)ethoxy-1,1,2,2-d4)pyridine 2-bromo-6-(2-(methoxy-d3)ethoxy-1,1,2,2-d4)pyridine 2645412-54-8 C8H3BrD7NO2
2-bromo-4-(2-methoxyethoxy)pyridine-3,5,6-d3 2-bromo-4-(2-methoxyethoxy)pyridine-3,5,6-d3 2645416-57-3 C8H7BrD3NO2
3-bromo-5-((methoxy-d3)methyl-d2)pyridine 3-bromo-5-((methoxy-d3)methyl-d2)pyridine 2645411-91-0 C7H3BrD5NO
5-bromo-2-((methoxy-d3)methyl-d2)pyrimidine-4,6-d2 5-bromo-2-((methoxy-d3)methyl-d2)pyrimidine-4,6-d2 2645415-72-9 C6BrD7N2O
6-((methoxy-d3)methyl-d2)pyridin-2-amine 6-((methoxy-d3)methyl-d2)pyridin-2-amine 2645418-69-3 C7H5D5N2O
2-(methoxymethyl)pyridin-3,5,6-d3-4-amine 2-(methoxymethyl)pyridin-3,5,6-d3-4-amine 2645412-02-6 C7H7D3N2O
2,3-dibromo-5-fluoropyridine-4,6-d2 2,3-dibromo-5-fluoropyridine-4,6-d2 2645415-76-3 C5Br2D2FN
7-bromo-[1,2,4]triazolo[1,5-a]pyridine-2,5,6,8-d4 7-bromo-[1,2,4]triazolo[1,5-a]pyridine-2,5,6,8-d4 2645412-45-7 C6BrD4N3
5-fluoro-4-(methyl-d3)pyridin-3,6-d2-2-amine 5-fluoro-4-(methyl-d3)pyridin-3,6-d2-2-amine 2645415-96-7 C6H2D5FN2
4-(methyl-d3)-2-(propan-2-yl-d7)pyridin-5,6-d2-3-amine 4-(methyl-d3)-2-(propan-2-yl-d7)pyridin-5,6-d2-3-amine 2645413-47-2 C9H2D12N2
4-bromo-2-fluoro-6-methylpyridine-3,5-d2 4-bromo-2-fluoro-6-methylpyridine-3,5-d2 2645417-20-3 C6H3BrD2FN
2-methylpyridin-3,5,6-d3-4-ol 2-methylpyridin-3,5,6-d3-4-ol 2645411-70-5 C6H4D3NO
2-methylpyridin-4,5,6-d3-3-amine 2-methylpyridin-4,5,6-d3-3-amine 2645411-72-7 C6H5D3N2
5-bromo-N-methylpyridin-2,4,6-d3-3-amine 5-bromo-N-methylpyridin-2,4,6-d3-3-amine 2645413-54-1 C6H4BrD3N2
2,6-dibromo-4-fluoropyridine-3,5-d2 2,6-dibromo-4-fluoropyridine-3,5-d2 2645412-50-4 C5Br2D2FN
1H-pyrrolo[2,3-c]pyridine-2-d 1H-pyrrolo[2,3-c]pyridine-2-d 2697155-70-5 C7H5DN2
4-bromo-1H-pyrrolo[2,3-c]pyridine-2,3,5,7-d4 4-bromo-1H-pyrrolo[2,3-c]pyridine-2,3,5,7-d4 2697162-75-5 C7HBrD4N2
3-bromo-5-fluoro-2-(methyl-d3)pyridine 3-bromo-5-fluoro-2-(methyl-d3)pyridine 2697155-55-6 C6H2BrD3FN
tert-butyl 4-(2-bromopyridin-4-yl)piperidine-1-carboxylate-2,2,3,3,4,5,5,6,6-d9 tert-butyl 4-(2-bromopyridin-4-yl)piperidine-1-carboxylate-2,2,3,3,4,5,5,6,6-d9 2697155-61-4 C15H12BrD9N2O2
tert-butyl 4-(5-bromopyrimidin-2-yl-4,6-d2)piperidine-1-carboxylate-2,2,3,3,4,5,5,6,6-d9 tert-butyl 4-(5-bromopyrimidin-2-yl-4,6-d2)piperidine-1-carboxylate-2,2,3,3,4,5,5,6,6-d9 2697156-24-2 C14H9BrD11N3O2
4-bromo-2-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine 4-bromo-2-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine 2697155-43-2 C10H7BrD5NO
3-bromo-5-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine-2,4,6-d3 3-bromo-5-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyridine-2,4,6-d3 2697163-13-4 C10H4BrD8NO
5-bromo-2-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyrimidine 5-bromo-2-(tetrahydro-2H-pyran-4-yl-3,3,4,5,5-d5)pyrimidine 2697156-85-5 C9H6BrD5N2O
4-bromo-2,6-bis(methyl-d3)pyrimidine 4-bromo-2,6-bis(methyl-d3)pyrimidine 2697155-56-7 C6HBrD6N2
2,6-bis(methyl-d3)pyrimidin-4(3H)-one 2,6-bis(methyl-d3)pyrimidin-4(3H)-one 2697162-89-1 C6H2D6N2O
4-bromo-5-(methoxy-d3)-2-(trifluoromethyl)pyridine 4-bromo-5-(methoxy-d3)-2-(trifluoromethyl)pyridine 2697156-42-4 C7H2BrD3F3NO
6-(2-(methyl-d3)propan-2-yl-1,1,1,3,3,3-d6)pyridin-2,4,5-d3-3-amine 6-(2-(methyl-d3)propan-2-yl-1,1,1,3,3,3-d6)pyridin-2,4,5-d3-3-amine 2697162-64-2 C9H2D12N2
2-(ethyl-d5)-6-fluoropyridine 2-(ethyl-d5)-6-fluoropyridine 2697156-47-9 C7H3D5FN
methyl 1-(methyl-d3)-1,2,3,6-tetrahydropyridine-4-carboxylate-2,2,3,3,5,6,6-d7 methyl 1-(methyl-d3)-1,2,3,6-tetrahydropyridine-4-carboxylate-2,2,3,3,5,6,6-d7 2697156-13-9 C8H3D10NO2
2,4-dibromo-5-(methoxy-d3)pyridine-3,6-d2 2,4-dibromo-5-(methoxy-d3)pyridine-3,6-d2 2697155-96-5 C6Br2D5NO
6-(difluoromethyl-d)pyridin-2,4,5-d3-3-amine 6-(difluoromethyl-d)pyridin-2,4,5-d3-3-amine 2697156-18-4 C6H2D4F2N2
5,5'-dibromo-2,2'-bipyridine-3,3',4,4',6,6'-d6 5,5'-dibromo-2,2'-bipyridine-3,3',4,4',6,6'-d6 2711075-27-1 C10Br2D6N2
2,2'-bipyridin]-d7-5-ol 2,2'-bipyridin]-d7-5-ol 2711075-32-8 C10HD7N2O
2-(difluoromethyl)pyridin-3,5,6-d3-4-ol 2-(difluoromethyl)pyridin-3,5,6-d3-4-ol 2710298-41-0 C6H2D3F2NO
2-bromo-3-fluoropyridine-4,5,6-d3 2-bromo-3-fluoropyridine-4,5,6-d3 2622983-73-5 C5HBrD2FN
3-bromo-2-methoxypyridine-4,5,6-d3 3-bromo-2-methoxypyridine-4,5,6-d3 2768657-40-3 C6H3BrD3NO
3-bromo-2-(trifluoromethyl)pyridine-4,5,6-d3 3-bromo-2-(trifluoromethyl)pyridine-4,5,6-d3 2768656-27-3 C6BrD3F3N
tert-butyl 3-(6-bromopyridin-3-yl)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(6-bromopyridin-3-yl)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2768655-71-4 C15H12BrD9N2O2
tert-butyl 3-(4-bromopyridin-2-yl-3,5,6-d3)piperidine-1-carboxylate tert-butyl 3-(4-bromopyridin-2-yl-3,5,6-d3)piperidine-1-carboxylate 2768654-66-4 C15H18BrD3N2O2
tert-butyl 3-(5-bromopyridin-3-yl-2,4,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(5-bromopyridin-3-yl-2,4,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2768657-77-6 C15H9BrD12N2O2
tert-butyl 3-(2-aminopyridin-4-yl-3,5,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(2-aminopyridin-4-yl-3,5,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2768655-75-8 C15H11D12N3O2
tert-butyl 3-(2-aminopyridin-4-yl)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(2-aminopyridin-4-yl)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2768655-58-7 C15H14D9N3O2
2-(trifluoromethyl)pyridin-4,5,6-d3-3-ol 2-(trifluoromethyl)pyridin-4,5,6-d3-3-ol 2768655-57-6 C6HD3F3NO
5-bromo-2-fluoro-3-(methyl-d3)pyridine-4,6-d2 5-bromo-2-fluoro-3-(methyl-d3)pyridine-4,6-d2 2256740-02-8 C6BrD5FN
5-bromo-4-(methyl-d3)pyridin-2-amine 5-bromo-4-(methyl-d3)pyridin-2-amine 2256740-09-5 C6H4BrD3N2
4-bromo-5-(methyl-d3)pyridin-3,6-d2-2-ol 4-bromo-5-(methyl-d3)pyridin-3,6-d2-2-ol 2256740-17-5 C6HBrD5NO
3-bromo-4-methyl-2-(methyl-d3)pyridine-5,6-d2 3-bromo-4-methyl-2-(methyl-d3)pyridine-5,6-d2 2768656-24-0 C7H3BrD5N
4-bromo-2-chloro-6-methoxypyridine-3,5-d2 4-bromo-2-chloro-6-methoxypyridine-3,5-d2 2806729-15-5 C6H3BrClD2NO
2-(5-aminopyrimidin-2-yl-4,6-d2)propan-1,1,1,3,3,3-d6-2-ol 2-(5-aminopyrimidin-2-yl-4,6-d2)propan-1,1,1,3,3,3-d6-2-ol 2806719-93-5 C7H3D8N3O
tert-butyl 4-bromo-3-(methyl-d3)-3,6-dihydropyridine-1(2H)-carboxylate-2,2,3,5,6,6-d6 tert-butyl 4-bromo-3-(methyl-d3)-3,6-dihydropyridine-1(2H)-carboxylate-2,2,3,5,6,6-d6 2806729-18-8 C11H9BrD9NO2
4-bromo-2-(ethyl-d5)pyrimidine-5,6-d2 4-bromo-2-(ethyl-d5)pyrimidine-5,6-d2 2241865-71-2 C6BrD7N2
2-chloro-5-(ethyl-d5)pyridin-4-amine 2-chloro-5-(ethyl-d5)pyridin-4-amine 2806728-54-9 C7H4ClD5N2
2-bromo-5-iodopyridin-3,6-d2-4-amine 2-bromo-5-iodopyridin-3,6-d2-4-amine 2806718-58-9 C5H2BrD2IN2
4-bromo-3-(methyl-d3)pyridine 4-bromo-3-(methyl-d3)pyridine 2806718-61-4
3-bromo-2,5-bis(methyl-d3)-6-(trifluoromethyl)pyridine-4-d 3-bromo-2,5-bis(methyl-d3)-6-(trifluoromethyl)pyridine-4-d 2826916-15-6 C8BrD7F3N
2-bromo-4-chloro-6-(methyl-d3)pyrimidine-5-d 2-bromo-4-chloro-6-(methyl-d3)pyrimidine-5-d 2826916-16-7 C5BrClD4N2
5-bromo-3-methoxy-2-(methyl-d3)pyridine-4,6-d2 5-bromo-3-methoxy-2-(methyl-d3)pyridine-4,6-d2 2826917-43-3 C7H3BrD5NO
5-(methoxy-d3)-6-(methyl-d3)pyridin-3-amine 5-(methoxy-d3)-6-(methyl-d3)pyridin-3-amine 2826916-71-4 C7H4D6N2O
3-bromo-4-chloro-5-nitropyridine-2,6-d2 3-bromo-4-chloro-5-nitropyridine-2,6-d2 2826917-21-7 C5BrClD2N2O2
6-chloro-N-(methyl-d3)pyridazine-3-carboxamide 6-chloro-N-(methyl-d3)pyridazine-3-carboxamide 2826916-79-2 C6H3ClD3N3O
5-chloro-N-methylpyrimidine-4,6-d2-2-carboxamide 5-chloro-N-methylpyrimidine-4,6-d2-2-carboxamide 2826917-27-3 C6H4ClD2N3O
2-bromo-6-(fluoromethyl-d2)pyridine-3,4,5-d3 2-bromo-6-(fluoromethyl-d2)pyridine-3,4,5-d3 2891518-34-4 C6BrD5FN
4-bromo-2-(fluoromethyl-d2)pyrimidine 4-bromo-2-(fluoromethyl-d2)pyrimidine 2891520-71-9 C5H2BrD2FN2
3-bromo-6-(fluoromethyl-d2)pyridazine-4,5-d2 3-bromo-6-(fluoromethyl-d2)pyridazine-4,5-d2 2891520-66-2 C5BrD4FN2
3-bromo-6-fluoro-2-(methoxy-d3)pyridine 3-bromo-6-fluoro-2-(methoxy-d3)pyridine 2891520-28-6 C6H2BrD3FNO
4-bromo-2-(methyl-d3)-3-(trifluoromethyl)pyridine 4-bromo-2-(methyl-d3)-3-(trifluoromethyl)pyridine 2891521-22-3 C7H2BrD3F3N
5-bromo-2-methyl-3-(trifluoromethyl)pyridine-4,6-d2 5-bromo-2-methyl-3-(trifluoromethyl)pyridine-4,6-d2 2891511-08-1 C7H3BrD2F3N
6-(methyl-d3)-5-(trifluoromethyl)pyridin-2-amine 6-(methyl-d3)-5-(trifluoromethyl)pyridin-2-amine 2891520-78-6 C7H4D3F3N2
6-bromo-3-methyl-2-(trifluoromethyl)pyridine-4,5-d2 6-bromo-3-methyl-2-(trifluoromethyl)pyridine-4,5-d2 2891521-08-5 C7H3BrD2F3N
4-methyl-6-(trifluoromethyl)pyridin-3,5-d2-2-amine 4-methyl-6-(trifluoromethyl)pyridin-3,5-d2-2-amine 2891518-39-9 C7H5D2F3N2
2-bromo-3-(methyl-d3)-6-(trifluoromethyl)pyridine 2-bromo-3-(methyl-d3)-6-(trifluoromethyl)pyridine 2891511-22-9 C7H2BrD3F3N
4-bromo-2-(1,1-difluoroethyl)pyridine-3,5,6-d3 4-bromo-2-(1,1-difluoroethyl)pyridine-3,5,6-d3 2891520-86-6 C7H3BrD3F2N
3-bromo-5-(1,1-difluoroethyl-2,2,2-d3)pyridine-2,4,6-d3 3-bromo-5-(1,1-difluoroethyl-2,2,2-d3)pyridine-2,4,6-d3 2891511-79-6 C7BrD6F2N
4-bromo-2-(1,1-difluoroethyl-2,2,2-d3)pyrimidine-5,6-d2 4-bromo-2-(1,1-difluoroethyl-2,2,2-d3)pyrimidine-5,6-d2 2891517-88-5 C6BrD5F2N2
2-bromo-4-(1,1-difluoroethyl)pyrimidine-5,6-d2 2-bromo-4-(1,1-difluoroethyl)pyrimidine-5,6-d2 2891512-36-8 C6H3BrD2F2N2
6-bromo-5-methylpyridin-3,4-d2-2-amine 6-bromo-5-methylpyridin-3,4-d2-2-amine 2891512-86-8 C6H5BrD2N2
2-bromo-6-methoxypyridine-3,4,5-d3 2-bromo-6-methoxypyridine-3,4,5-d3 2610635-37-3 C6H3BrD3NO
4-bromo-3-(methoxy-d2)pyridine-2,5,6-d3 4-bromo-3-(methoxy-d2)pyridine-2,5,6-d3 2891512-87-9 C6HBrD5NO
2-bromo-3-methoxypyridine-4,5,6-d3 2-bromo-3-methoxypyridine-4,5,6-d3 2891512-15-3 C6H3BrD3NO
2-bromo-4-methoxypyrimidine-5,6-d2 2-bromo-4-methoxypyrimidine-5,6-d2 2891511-62-7 C5H3BrD2N2O
5-bromo-4-(methoxy-d2)pyrimidine-2,6-d2 5-bromo-4-(methoxy-d2)pyrimidine-2,6-d2 2891517-16-9 C5HBrD4N2O
1H-pyrrolo[3,2-b]pyridin-2,3,6,7-d4-5-ol 1H-pyrrolo[3,2-b]pyridin-2,3,6,7-d4-5-ol 2891518-05-9 C7H2D4N2O
4-iodo-2-(methyl-d3)-5-(trifluoromethyl)pyridine 4-iodo-2-(methyl-d3)-5-(trifluoromethyl)pyridine 2891518-17-3 C7H2D3F3IN
2,4-dichloropyrido[3,4-d]pyrimidine-5,6,8-d3 2,4-dichloropyrido[3,4-d]pyrimidine-5,6,8-d3
3,5-dibromo-4-(methyl-d3)pyridine-2,6-d2 3,5-dibromo-4-(methyl-d3)pyridine-2,6-d2
3-bromo-5-fluoropyridine-4,6-d2 3-bromo-5-fluoropyridine-4,6-d2
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