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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-Bromo-4-(3-methoxyphenyl)thiophene 2-Bromo-4-(3-methoxyphenyl)thiophene 1159819-99-4 C11H9BrOS
2-Bromo-4-(3-thienyl)thiazole 2-Bromo-4-(3-thienyl)thiazole 1215074-13-7 C7H4BrNS2
2-Bromo-4-(4-aminophenyl)pyridine 2-Bromo-4-(4-aminophenyl)pyridine 1563534-17-7 C11H9BrN2
2-Bromo-4-(4-cyanophenyl)pyridine 2-Bromo-4-(4-cyanophenyl)pyridine 1563531-34-9 C12H7BrN2
2-Bromo-4-(4-thiazolyl)pyridine 2-Bromo-4-(4-thiazolyl)pyridine 1353857-00-7 C8H5BrN2S
2-Bromo-4-(4-trifluoromethylphenyl)pyridine 2-Bromo-4-(4-trifluoromethylphenyl)pyridine 1215072-06-2 C12H7BrF3N
2-Bromo-4-(cyclohexyl)thiophene 2-Bromo-4-(cyclohexyl)thiophene 82834-47-7 C10H13BrS
2-Bromo-4-(cyclopentyl)thiophene 2-Bromo-4-(cyclopentyl)thiophene 1159820-33-3 C9H11BrS
2-Bromo-4-(N-Boc-piperidin-4-yl)pyridine 2-Bromo-4-(N-Boc-piperidin-4-yl)pyridine 1563530-39-1 C15H21BrN2O2
2-Bromo-4-(tetrahydropyran-3-yl)pyridine 2-Bromo-4-(tetrahydropyran-3-yl)pyridine 1159814-88-6 C10H12BrNO
2-Bromo-4-amino-5-(2-methoxyphenyl)pyridine 2-Bromo-4-amino-5-(2-methoxyphenyl)pyridine 1381937-55-8 C12H11BrN2O
2-Bromo-4-amino-5-(4-pyridyl)pyridine 2-Bromo-4-amino-5-(4-pyridyl)pyridine 1381944-06-4 C10H8BrN3
2-Bromo-4-amino-5-(iso-propyl)pyrimidine 2-Bromo-4-amino-5-(iso-propyl)pyrimidine 1381936-76-0 C7H10BrN3
2-Bromo-4-chloro-6-(3-fluorophenyl)pyrimidine 2-Bromo-4-chloro-6-(3-fluorophenyl)pyrimidine 1434127-37-3 C10H5BrClFN2
2-Bromo-4-chloro-6-(3-trifluoromethylphenyl)pyrimidine 2-Bromo-4-chloro-6-(3-trifluoromethylphenyl)pyrimidine 1034619-65-2 C11H5BrClF3N2
2-bromo-5-(1H-imidazol-1-yl-d3)pyridine-3,4,6-d3 2-bromo-5-(1H-imidazol-1-yl-d3)pyridine-3,4,6-d3 2256707-22-7 C8H6BrN3
2-bromo-5-(1H-pyrazol-1-yl-d3)pyridine-3,4,6-d3 2-bromo-5-(1H-pyrazol-1-yl-d3)pyridine-3,4,6-d3 2256707-37-4 C8BrD6N3
2-Bromo-5-(2-fluorolphenyl)thiazole 2-Bromo-5-(2-fluorolphenyl)thiazole 1215072-37-9 C9H5BrFNS
2-Bromo-5-(2-furyl)pyridine 2-Bromo-5-(2-furyl)pyridine 1142197-48-5 C9H6BrNO
2-Bromo-5-(2-thiazolyl)furan 2-Bromo-5-(2-thiazolyl)furan 1159815-07-2 C7H4BrNOS
2-Bromo-5-(3-amino-5-pyridyl)pyridine 2-Bromo-5-(3-amino-5-pyridyl)pyridine 1142193-93-8 C10H8BrN3
2-Bromo-5-(3-hydroxyphenyl)pyridine 2-Bromo-5-(3-hydroxyphenyl)pyridine 1142193-72-3 C11H8BrNO
2-Bromo-5-(3-methyl-1H-pyrazol-1-yl)pyridine 2-Bromo-5-(3-methyl-1H-pyrazol-1-yl)pyridine 1314355-41-3 C9H8BrN3
2-Bromo-5-(3-trifluoromethylphenyl)thiazole 2-Bromo-5-(3-trifluoromethylphenyl)thiazole 1215072-33-5 C10H5BrF3NS
2-Bromo-5-(4-tolyl)pyridine 2-Bromo-5-(4-tolyl)pyridine 1142197-36-1 C12H10BrN
2-Bromo-5-amino-4-(2-fluorophenyl)pyridine 2-Bromo-5-amino-4-(2-fluorophenyl)pyridine 1381934-49-1 C11H8BrFN2
2-Bromo-5-amino-4-(2-pyridyl)pyridine 2-Bromo-5-amino-4-(2-pyridyl)pyridine 1381934-05-9 C10H8BrN3
2-Bromo-5-amino-4-(3-fluorophenyl)pyridine 2-Bromo-5-amino-4-(3-fluorophenyl)pyridine 1381941-35-0 C11H8BrFN2
2-Bromo-5-amino-4-(4-methylpiperidin-1-yl)pyridine 2-Bromo-5-amino-4-(4-methylpiperidin-1-yl)pyridine 1381933-91-0 C11H16BrN3
2-Bromo-5-amino-4-(cyclobutyl)pyridine 2-Bromo-5-amino-4-(cyclobutyl)pyridine 1381934-51-5 C9H11BrN2
2-Bromo-6-(2-aminophenyl)pyridine 2-Bromo-6-(2-aminophenyl)pyridine 1563530-35-7 C11H9BrN2
2-Bromo-6-(2-fluorophenyl)pyridine 2-Bromo-6-(2-fluorophenyl)pyridine 1142196-95-9 C11H7BrFN
2-BROMO-6-(3-AMINOPHENYL)PYRIDINE 2-BROMO-6-(3-AMINOPHENYL)PYRIDINE 1563533-51-6 C11H9BrN2
2-BROMO-6-(4-AMINOPHENYL)PYRIDINE 2-BROMO-6-(4-AMINOPHENYL)PYRIDINE 1563533-57-2 C11H9BrN2
2-Bromo-6-(5-pyrimidyl)pyrazine 2-Bromo-6-(5-pyrimidyl)pyrazine 1159814-86-4 C8H5BrN4
2-Bromo-6-(tetrahydropyran-4-yl)pyridine 2-Bromo-6-(tetrahydropyran-4-yl)pyridine 1159817-58-9 C10H12BrNO
2-CHLORO-3-(1H-PYRAZOL-4-YL)PYRIDINE 2-CHLORO-3-(1H-PYRAZOL-4-YL)PYRIDINE 1563529-57-6 C8H6ClN3
2-Chloro-4-(2-pyridyl)-6-amino-1,3,5-triazine 2-Chloro-4-(2-pyridyl)-6-amino-1,3,5-triazine 1303967-68-1 C8H6ClN5
2-Chloro-4-(2-tolyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(2-tolyl)-6-hydroxy-1,3,5-triazine 1303967-27-2 C10H8ClN3O
2-Chloro-4-(3-pyridyl)-6-methoxy-1,3,5-triazine 2-Chloro-4-(3-pyridyl)-6-methoxy-1,3,5-triazine 1303967-70-5 C9H7ClN4O
2-Chloro-4-(3-trifluoromethylphenyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(3-trifluoromethylphenyl)-6-hydroxy-1,3,5-triazine 1303967-31-8 C10H5ClF3N3O
2-Chloro-4-(4-trifluoromethylphenyl)-6-methoxy-1,3,5-triazine 2-Chloro-4-(4-trifluoromethylphenyl)-6-methoxy-1,3,5-triazine 1303967-80-7 C11H7ClF3N3O
2-Chloro-4-(iso-propyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(iso-propyl)-6-hydroxy-1,3,5-triazine 1303967-69-2 C6H8ClN3O
2-CHLORO-4-AMINO-3-(2-THIENYL)PYRIDINE 2-CHLORO-4-AMINO-3-(2-THIENYL)PYRIDINE 1381938-64-2 C9H7ClN2S
2-CHLORO-4-AMINO-3-(4-TRIFLUOROMETHYLPHENYL)PYRIDINE 2-CHLORO-4-AMINO-3-(4-TRIFLUOROMETHYLPHENYL)PYRIDINE 1381935-26-7 C12H8ClF3N2
2-CHLORO-4-AMINO-3-(CYCLOPROPYL)PYRIDINE 2-CHLORO-4-AMINO-3-(CYCLOPROPYL)PYRIDINE 1381935-49-4 C8H9ClN2
2-Chloro-4-amino-5-(3-fluorophenyl)pyridine 2-Chloro-4-amino-5-(3-fluorophenyl)pyridine 1381934-17-3 C11H8ClFN2
2-Chloro-4-amino-5-(3-tolyl)pyridine 2-Chloro-4-amino-5-(3-tolyl)pyridine 1381938-81-3 C12H11ClN2
2-Chloro-4-amino-6-(4-trifluoromethylphenyl)pyrimidine 2-Chloro-4-amino-6-(4-trifluoromethylphenyl)pyrimidine 1353856-47-9 C11H7ClF3N3
2-Chloro-4-amino-6-(n-propyl)pyrimidine 2-Chloro-4-amino-6-(n-propyl)pyrimidine 1353854-13-3 C7H10ClN3
2-Chloro-4-bromo-6-(3-pyridyl)pyrimidine 2-Chloro-4-bromo-6-(3-pyridyl)pyrimidine 1412953-56-0 C9H5BrClN3
2-Chloro-4-bromo-6-(4-fluorophenyl)pyrimidine 2-Chloro-4-bromo-6-(4-fluorophenyl)pyrimidine 1412953-36-6 C10H5BrClFN2
2-Chloro-4-bromo-6-(iso-butyl)pyrimidine 2-Chloro-4-bromo-6-(iso-butyl)pyrimidine 1412960-08-7 C8H10BrClN2
2-Chloro-4-bromo-6-(thiazol-2-yl)pyrimidine 2-Chloro-4-bromo-6-(thiazol-2-yl)pyrimidine 1412960-06-5 C7H3BrClN3S
2-Chloro-4-ethyl-6-hydroxy-1,3,5-triazine 2-Chloro-4-ethyl-6-hydroxy-1,3,5-triazine 1303967-25-0 C5H6ClN3O
2-Chloro-4-phenyl-6-hydroxy-1,3,5-triazine 2-Chloro-4-phenyl-6-hydroxy-1,3,5-triazine 1303967-87-4 C9H6ClN3O
2-CHLORO-5-(3-AMINOPHENYL)PYRIMIDINE 2-CHLORO-5-(3-AMINOPHENYL)PYRIMIDINE 1563534-81-5 C10H8ClN3
2-Chloro-5-(3-tetrahydropyranyl)pyrimidine 2-Chloro-5-(3-tetrahydropyranyl)pyrimidine 1363253-97-7 C9H11ClN2O
2-cyclopropoxy-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-cyclopropoxy-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256754-71-7 C14H19BFNO3
2-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 2-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 2241870-43-7 C14H17BD3NO2
2-fluoro-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazol-1-yl)pyridine 2-fluoro-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazol-1-yl)pyridine 2256758-13-9 C13H16BFN4O2
2-Hydroxy-4-(2-furyl)pyridine 2-Hydroxy-4-(2-furyl)pyridine 1159817-23-8 C9H7NO2
2-Hydroxy-4-(2-methylpyrimidyl-5-yl)thiazole 2-Hydroxy-4-(2-methylpyrimidyl-5-yl)thiazole 1215072-39-1 C8H7N3OS
2-Hydroxy-4-(3-trifluoromethylphenyl)pyridine 2-Hydroxy-4-(3-trifluoromethylphenyl)pyridine 1215071-69-4 C12H8F3NO
2-Hydroxy-5-(2-hydroxyphenyl)pyridine 2-Hydroxy-5-(2-hydroxyphenyl)pyridine 1111102-89-6 C11H9NO2
2-Hydroxy-5-(2-methyl-4-fluorophenyl)thiazole 2-Hydroxy-5-(2-methyl-4-fluorophenyl)thiazole 1215073-03-2 C10H8FNOS
2-Hydroxy-5-(3,4-difluorophenyl)thiazole 2-Hydroxy-5-(3,4-difluorophenyl)thiazole 1215071-80-9 C9H5F2NOS
2-Hydroxy-5-(3-chlorophenyl)pyridine 2-Hydroxy-5-(3-chlorophenyl)pyridine 1111116-08-5 C11H8ClNO
2-Hydroxy-5-(3-thienyl)pyridine 2-Hydroxy-5-(3-thienyl)pyridine 1111116-05-2 C9H7NOS
2-Hydroxy-5-(3-tolyl)thiazole 2-Hydroxy-5-(3-tolyl)thiazole 1215072-41-5 C10H9NOS
2-Hydroxy-5-(4-tolyl)pyrimidine 2-Hydroxy-5-(4-tolyl)pyrimidine 27956-36-1 C11H10N2O
2-Hydroxy-5-(cyclopropyl)pyrimidine 2-Hydroxy-5-(cyclopropyl)pyrimidine 1353854-40-6 C7H8N2O
2-Hydroxy-5-(n-propyl)pyridine 2-Hydroxy-5-(n-propyl)pyridine 72323-57-0 C8H11NO
2-Hydroxy-6-(2-methoxyphenyl)pyridine 2-Hydroxy-6-(2-methoxyphenyl)pyridine 1111114-62-5 C12H11NO2
2-Hydroxy-6-(4-tert-butylphenyl)pyridine 2-Hydroxy-6-(4-tert-butylphenyl)pyridine 1111110-49-6 C15H17NO
2-Hydroxy-6-(n-propyl)pyridine 2-Hydroxy-6-(n-propyl)pyridine 57740-48-4 C8H11NO
3-(1,3-THIAZOL-5-YL)PYRIDIN-2-AMINE 3-(1,3-THIAZOL-5-YL)PYRIDIN-2-AMINE 1368100-37-1 C8H7N3S
3-(2-METHYL-1H-IMIDAZOL-1-YL)PYRIDIN-2-AMINE 3-(2-METHYL-1H-IMIDAZOL-1-YL)PYRIDIN-2-AMINE 1407153-47-2 C9H10N4
3-(3-AMINOPHENYL)PYRIDIN-4-AMINE 3-(3-AMINOPHENYL)PYRIDIN-4-AMINE 1563532-63-7 C11H11N3
3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-3,5-d2)pyridine-2,4,5,6-d4 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-3,5-d2)pyridine-2,4,5,6-d4 2256710-39-9 C14H18BN3O2
3-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,5,6-d3 3-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,5,6-d3 2256706-41-7 C15H20BN3O2
3-(4-bromo-1H-imidazol-1-yl-2,5-d2)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,5,6-d3 3-(4-bromo-1H-imidazol-1-yl-2,5-d2)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,5,6-d3 2256706-75-7 C14H12BBrD5N3O2
3-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,5,6-d3 3-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,5,6-d3 2256706-52-0 C14H12BBrD5N3O2
3-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDIN-2-AMINE 3-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDIN-2-AMINE 1407153-44-9 C9H10N4
3-(6-AMINOPYRIDIN-2-YL)BENZONITRILE 3-(6-AMINOPYRIDIN-2-YL)BENZONITRILE 1183082-28-1 C12H9N3
3-(methyl-d3)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-4,5-d2)pyridine-4,5,6-d3 3-(methyl-d3)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-4,5-d2)pyridine-4,5,6-d3 2256705-91-4 C15H12BD8N3O2
3-(Thiazol-5-yl)bromobenzene 3-(Thiazol-5-yl)bromobenzene 1563530-28-8 C9H6BrNS
3,4-Dibromo-2-(4-methoxyphenyl)pyridine 3,4-Dibromo-2-(4-methoxyphenyl)pyridine 1381942-47-7 C12H9Br2NO
3,4-Dibromo-2-(4-tolyl)pyridine 3,4-Dibromo-2-(4-tolyl)pyridine 1381941-41-8 C12H9Br2N
3,4-Dibromo-2-(n-propyl)pyridine 3,4-Dibromo-2-(n-propyl)pyridine 1381934-48-0 C8H9Br2N
3,4-Dibromo-6-(3-fluorophenyl)pyridine 3,4-Dibromo-6-(3-fluorophenyl)pyridine 1381933-14-7 C11H6Br2FN
3,4-Dibromo-6-(3-methylpiperidin-1-yl)pyridine 3,4-Dibromo-6-(3-methylpiperidin-1-yl)pyridine 1381942-26-2 C11H14Br2N2
3,4-Dibromo-6-(5-pyrimidyl)pyridine 3,4-Dibromo-6-(5-pyrimidyl)pyridine 1381942-27-3 C9H5Br2N3
3,4-Dibromo-6-(piperidino)pyridine 3,4-Dibromo-6-(piperidino)pyridine 1381933-21-6 C10H12Br2N2
3,5-Dibromo-6-(2-trifluoromethylphenyl)pyridine 3,5-Dibromo-6-(2-trifluoromethylphenyl)pyridine 1399482-13-3 C12H6Br2F3N
3-acetyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one 3-acetyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one 2256755-05-0 C13H18BNO4
3-AMINO-2-CYCLOHEXYLPYRIDINE 3-AMINO-2-CYCLOHEXYLPYRIDINE 1417519-47-1 C11H16N2
3-AMINO-4-(2-METHYLPIPERIDIN-1-YL)PYRIDINE 3-AMINO-4-(2-METHYLPIPERIDIN-1-YL)PYRIDINE 1082897-86-6 C11H17N3
3-Amino-5-(1H-pyridin-2-one)pyridine 3-Amino-5-(1H-pyridin-2-one)pyridine 1314354-38-5 C10H9N3O
3-AMINO-5-(3-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 3-AMINO-5-(3-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 1314353-70-2 C9H10N4
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