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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-6-(2-methoxyphenyl)pyridine 2-Bromo-6-(2-methoxyphenyl)pyridine 1142196-80-2 C12H10BrNO
2-Bromo-6-(3-methoxyphenyl)pyridine 2-Bromo-6-(3-methoxyphenyl)pyridine 851595-28-3 C12H10BrNO
2-Bromo-6-(4-fluorophenyl)pyridine 2-Bromo-6-(4-fluorophenyl)pyridine 1142196-75-5 C11H7BrFN
2-Bromol-4-amino-5-(2-furyl)pyrimidine 2-Bromol-4-amino-5-(2-furyl)pyrimidine 1381944-18-8 C8H6BrN3O
2-Chloro-3-(oxan-2-yl)pyridine 2-Chloro-3-(oxan-2-yl)pyridine 1622836-00-3 C10H12ClNO
2-Chloro-4-(2-furyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(2-furyl)-6-hydroxy-1,3,5-triazine 1303967-45-4 C7H4ClN3O2
2-Chloro-4-(2-trifluoromethylphenyl)-6-methoxy-1,3,5-triazine 2-Chloro-4-(2-trifluoromethylphenyl)-6-methoxy-1,3,5-triazine 1303967-71-6 C11H7ClF3N3O
2-Chloro-4-(3-furyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(3-furyl)-6-hydroxy-1,3,5-triazine 1303967-60-3 C7H4ClN3O2
2-Chloro-4-(4-fluorophenyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(4-fluorophenyl)-6-hydroxy-1,3,5-triazine 1303967-35-2 C9H5ClFN3O
2-Chloro-4-(4-pyridyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(4-pyridyl)-6-hydroxy-1,3,5-triazine 1303967-43-2 C8H5ClN4O
2-chloro-4-(tetrahydro-2H-pyran-4-yl)pyrimidine 2-chloro-4-(tetrahydro-2H-pyran-4-yl)pyrimidine 1434128-20-7 C9H11ClN2O
2-CHLORO-4-AMINO-3-(3-PYRIDYL)PYRIDINE 2-CHLORO-4-AMINO-3-(3-PYRIDYL)PYRIDINE 1381935-16-5 C10H8ClN3
2-CHLORO-4-AMINO-3-(4-CHLOROPHENYL)PYRIDINE 2-CHLORO-4-AMINO-3-(4-CHLOROPHENYL)PYRIDINE 1381935-34-7 C11H8Cl2N2
2-CHLORO-4-AMINO-3-(OXAN-4-YL)PYRIDINE 2-CHLORO-4-AMINO-3-(OXAN-4-YL)PYRIDINE 1563532-07-9 C10H13ClN2O
2-Chloro-4-amino-5-(4-pyridyl)pyridine 2-Chloro-4-amino-5-(4-pyridyl)pyridine 1381933-13-6 C10H8ClN3
2-Chloro-4-amino-5-(cyclohexyl)pyridine 2-Chloro-4-amino-5-(cyclohexyl)pyridine 1381936-30-6 C11H15ClN2
2-Chloro-4-amino-6-(3-chlorophenyl)pyrimidine 2-Chloro-4-amino-6-(3-chlorophenyl)pyrimidine 1353855-39-6 C10H7Cl2N3
2-Chloro-4-amino-6-(3-tolyl)pyrimidine 2-Chloro-4-amino-6-(3-tolyl)pyrimidine 1353856-46-8 C11H10ClN3
2-Chloro-4-bromo-6-(2-fluorophenyl)pyrimidine 2-Chloro-4-bromo-6-(2-fluorophenyl)pyrimidine 1412957-50-6 C10H5BrClFN2
2-Chloro-4-bromo-6-(2-tolyl)pyrimidine 2-Chloro-4-bromo-6-(2-tolyl)pyrimidine 1412959-19-3 C11H8BrClN2
2-Chloro-4-bromo-6-(4-tolyl)pyrimidine 2-Chloro-4-bromo-6-(4-tolyl)pyrimidine 1412953-67-3 C11H8BrClN2
2-Chloro-4-cyclohexyl-6-methoxy-1,3,5-triazine 2-Chloro-4-cyclohexyl-6-methoxy-1,3,5-triazine 1303967-94-3 C10H14ClN3O
2-Chloro-5-(2-chlorophenyl)pyrimidine 2-Chloro-5-(2-chlorophenyl)pyrimidine 75175-41-6 C10H6Cl2N2
2-Chloro-5-(2-methylpiperidin-1-yl)pyrimidine 2-Chloro-5-(2-methylpiperidin-1-yl)pyrimidine 1363253-86-4 C10H14ClN3
2-Chloro-5-(4-tetrahydropyranyl)pyrimidine 2-Chloro-5-(4-tetrahydropyranyl)pyrimidine 1363254-16-3 C9H11ClN2O
2-Chloro-5-(piperidin-3-yl)pyrimidine 2-Chloro-5-(piperidin-3-yl)pyrimidine 1622834-16-5 C9H12ClN3
2-Cyclohexyl-3,4,5-tribromopyridine 2-Cyclohexyl-3,4,5-tribromopyridine 1399480-47-7 C11H12Br3N
2-CYCLOPROPYLFURAN 2-CYCLOPROPYLFURAN 39763-87-6 C7H8O
2-Ethyl-3,4,5-tribromopyridine 2-Ethyl-3,4,5-tribromopyridine 1399480-70-6 C7H6Br3N
2-Fluoro-4-(thiazol-5-yl)bromobenzene 2-Fluoro-4-(thiazol-5-yl)bromobenzene 1563528-97-1 C9H5BrFNS
2-fluoro-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazol-1-yl)pyridine 2-fluoro-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazol-1-yl)pyridine 2256758-05-9 C13H16BFN4O2
2-Hydroxy-4-(2-methyl-4-fluorophenyl)thiazole 2-Hydroxy-4-(2-methyl-4-fluorophenyl)thiazole 1215072-65-3 C10H8FNOS
2-Hydroxy-4-(2-tolyl)thiophene 2-Hydroxy-4-(2-tolyl)thiophene 1243838-95-0 C11H10OS
2-Hydroxy-4-(3-tolyl)thiophene 2-Hydroxy-4-(3-tolyl)thiophene 1243839-13-5 C11H10OS
2-Hydroxy-4-(4-tolyl)thiophene 2-Hydroxy-4-(4-tolyl)thiophene 1243839-38-4 C11H10OS
2-Hydroxy-4-ethylthiophene 2-Hydroxy-4-ethylthiophene 1243839-37-3 C6H8OS
2-Hydroxy-5-(2-aminopyrimidyl-5-yl)thiazole 2-Hydroxy-5-(2-aminopyrimidyl-5-yl)thiazole 1215071-63-8 C7H6N4OS
2-Hydroxy-5-(2-methoxyphenyl)thiazole 2-Hydroxy-5-(2-methoxyphenyl)thiazole 1215074-10-4 C10H9NO2S
2-Hydroxy-5-(2-pyridyl)thiazole 2-Hydroxy-5-(2-pyridyl)thiazole 1215073-02-1 C8H6N2OS
2-Hydroxy-5-(2-tolyl)thiazole 2-Hydroxy-5-(2-tolyl)thiazole 1215072-21-1 C10H9NOS
2-Hydroxy-5-(3-fluorophenyl)pyrimidine 2-Hydroxy-5-(3-fluorophenyl)pyrimidine 75175-38-1 C10H7FN2O
2-Hydroxy-5-(3-methoxylphenyl)pyrimidine 2-Hydroxy-5-(3-methoxylphenyl)pyrimidine 1111103-55-9 C11H10N2O2
2-Hydroxy-5-(4-trifluoromethylphenyl)thiazole 2-Hydroxy-5-(4-trifluoromethylphenyl)thiazole 1215073-12-3 C10H6F3NOS
2-Hydroxy-5-(cyclohexyl)pyridine 2-Hydroxy-5-(cyclohexyl)pyridine 1159815-03-8 C11H15NO
2-Hydroxy-5-(piperidin-4-yl)thiazole 2-Hydroxy-5-(piperidin-4-yl)thiazole 1563535-15-8 C8H12N2OS
2-Hydroxy-6-(2-amino-5-pyrimidyl)pyrazine 2-Hydroxy-6-(2-amino-5-pyrimidyl)pyrazine 1159816-49-5 C8H7N5O
2-Hydroxy-6-(3-trifluoromethylphenyl)pyridine 2-Hydroxy-6-(3-trifluoromethylphenyl)pyridine 180606-04-6 C12H8F3NO
2-Hydroxy-6-(5-methyl-2-pyridyl)pyrazine 2-Hydroxy-6-(5-methyl-2-pyridyl)pyrazine 1159819-48-3 C10H9N3O
2-methoxy-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazol-1-yl)pyridine 2-methoxy-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazol-1-yl)pyridine 2256758-04-8 C14H19BN4O3
2-Methyl-3,4,5-tribromopyridine 2-Methyl-3,4,5-tribromopyridine 1188140-82-0 C6H4Br3N
3-(1,1-DIMETHYLETHYL)-4-PYRIDINAMINE 3-(1,1-DIMETHYLETHYL)-4-PYRIDINAMINE 1137671-76-1 C9H14N2
3-(1-METHYL-1H-PYRAZOL-4-YL)PYRIDIN-4-AMINE 3-(1-METHYL-1H-PYRAZOL-4-YL)PYRIDIN-4-AMINE 1343363-25-6 C9H10N4
3-(2-AMINOPHENYL)PYRIDIN-2-AMINE 3-(2-AMINOPHENYL)PYRIDIN-2-AMINE 1563531-33-8 C11H11N3
3-(3-AMINOPHENYL)PYRIDIN-2-AMINE 3-(3-AMINOPHENYL)PYRIDIN-2-AMINE 1369272-72-9 C11H11N3
3-(3-bromophenyl)-6-chloropyridazine-4,5-d2 3-(3-bromophenyl)-6-chloropyridazine-4,5-d2 2256712-36-2 C10H6BrClN2
3-(3-bromophenyl)pyridine-2,4,5,6-d4 3-(3-bromophenyl)pyridine-2,4,5,6-d4 2256711-97-2 C11H8BrN
3-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 3-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 2256706-83-7 C15H20BN3O2
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,5,6-d4 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,5,6-d4 2241875-38-5 C11H16BNO2
3-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridine-2,4,5,6-d4 3-(4-bromo-1H-pyrazol-1-yl-3,5-d2)pyridine-2,4,5,6-d4 2256709-94-9 C8H6BrN3
3-(4-bromophenyl)-5-(methyl-d3)pyridine-2,4,6-d3 3-(4-bromophenyl)-5-(methyl-d3)pyridine-2,4,6-d3 2256711-96-1 C12H10BrN
3-(4-BROMOPHENYL)PYRIDIN-4-AMINE 3-(4-BROMOPHENYL)PYRIDIN-4-AMINE 1555609-17-0 C11H9BrN2
3-(ethoxy-d5)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 3-(ethoxy-d5)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 2241875-01-2 C13H20BNO3
3-(ethyl-d5)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 3-(ethyl-d5)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 2241875-06-7 C13H20BNO2
3-(methyl-d3)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-4,5-d2)pyridazine-4,5-d2 3-(methyl-d3)-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-4,5-d2)pyridazine-4,5-d2 2256705-77-6 C14H19BN4O2
3-(OXOLAN-3-YLOXY)PYRIDIN-2-AMINE 3-(OXOLAN-3-YLOXY)PYRIDIN-2-AMINE 1342882-31-8 C9H12N2O2
3-(PIVALOYLOXY)-5-(PROP-1-EN-2-YL)PYRIDINE 3-(PIVALOYLOXY)-5-(PROP-1-EN-2-YL)PYRIDINE 1434127-72-6 C13H17NO2
3,4-Dibromo-2-(3-hydroxypiperidin-1-yl)pyridine 3,4-Dibromo-2-(3-hydroxypiperidin-1-yl)pyridine 1381938-70-0 C10H12Br2N2O
3,4-Dibromo-2-(3-thienyl)pyridine 3,4-Dibromo-2-(3-thienyl)pyridine 1381942-08-0 C9H5Br2NS
3,4-Dibromo-2-(cyclohexyl)pyridine 3,4-Dibromo-2-(cyclohexyl)pyridine 1381943-19-6 C11H13Br2N
3,4-dibromo-2-(methoxy-d3)pyridine-5,6-d2 3,4-dibromo-2-(methoxy-d3)pyridine-5,6-d2 2294949-04-3 C6H5Br2NO
3,4-Dibromo-6-(2-fluorophenyl)pyridine 3,4-Dibromo-6-(2-fluorophenyl)pyridine 1381934-90-2 C11H6Br2FN
3,4-Dibromo-6-(2-methylpiperidin-1-yl)pyridine 3,4-Dibromo-6-(2-methylpiperidin-1-yl)pyridine 1381943-95-8 C11H14Br2N2
3,4-Dibromo-6-(3-trifluoromethylphenyl)pyridine 3,4-Dibromo-6-(3-trifluoromethylphenyl)pyridine 1381943-80-1 C12H6Br2F3N
3,4-Dibromo-6-(4-methyl-1H-pyrazol-1-yl)pyridine 3,4-Dibromo-6-(4-methyl-1H-pyrazol-1-yl)pyridine 1381943-99-2 C9H7Br2N3
3,5-Dibromo-2-(2-furyl)pyridine 3,5-Dibromo-2-(2-furyl)pyridine 1399481-20-9 C9H5Br2NO
3,5-Dibromo-2-(3-pyridyl)pyridine 3,5-Dibromo-2-(3-pyridyl)pyridine 1399481-93-6 C10H6Br2N2
3,5-Dibromo-6-(3-trifluoromethylphenyl)pyridine 3,5-Dibromo-6-(3-trifluoromethylphenyl)pyridine 1399481-16-3 C12H6Br2F3N
3,5-Dibromo-6-(4-tolyl)pyridine 3,5-Dibromo-6-(4-tolyl)pyridine 1399481-10-7 C12H9Br2N
3-AMINO-2-(3-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 3-AMINO-2-(3-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 1006960-89-9 C9H10N4
3-AMINO-2-(5-PYRIMIDYL)PYRIDINE 3-AMINO-2-(5-PYRIMIDYL)PYRIDINE 1417518-32-1 C9H8N4
3-AMINO-4-(3,4-DIFLUOROPHENYL)PYRIDINE 3-AMINO-4-(3,4-DIFLUOROPHENYL)PYRIDINE 1374665-03-8 C11H8F2N2
3-AMINO-4-(3-METHYLPIPERIDIN-1-YL)PYRIDINE 3-AMINO-4-(3-METHYLPIPERIDIN-1-YL)PYRIDINE 1082897-84-4 C11H17N3
3-Amino-4-(diethylamino)pyridine 3-Amino-4-(diethylamino)pyridine 1082822-93-2 C9H15N3
3-Amino-4-(pyrazol-4-yl)pyridine 3-Amino-4-(pyrazol-4-yl)pyridine 1563533-31-2 C8H8N4
3-AMINO-5-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 3-AMINO-5-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 1314354-84-1 C9H10N4
3-AMINO-5-(5-THIAZOLYL)PYRIDINE 3-AMINO-5-(5-THIAZOLYL)PYRIDINE 1563534-22-4 C8H7N3S
3-Amino-5-(pyrazol-4-yl)pyridine 3-Amino-5-(pyrazol-4-yl)pyridine 1476040-40-0 C8H8N4
3-Amino-5-bromo-6-(4-tolyl)pyridine 3-Amino-5-bromo-6-(4-tolyl)pyridine 1399480-77-3 C12H11BrN2
3-AMINO-6-(5-PYRIMIDYL)PYRIDINE 3-AMINO-6-(5-PYRIMIDYL)PYRIDINE 1314354-31-8 C9H8N4
3-Amino-6-(pyrazol-4-yl)pyridine 3-Amino-6-(pyrazol-4-yl)pyridine 1254583-06-6 C8H8N4
3-BROMO-1-(PYRIMIDIN-5-YL)-1H-PYRAZOLE 3-BROMO-1-(PYRIMIDIN-5-YL)-1H-PYRAZOLE 1622843-56-4 C7H5BrN4
3-Bromo-2-(2-chlorophenyl)pyridine 3-Bromo-2-(2-chlorophenyl)pyridine 1417518-79-6 C11H7BrClN
3-BROMO-2-(2-METHOXYPHENYL)PYRIDIN-4-AMINE 3-BROMO-2-(2-METHOXYPHENYL)PYRIDIN-4-AMINE 1381942-14-8 C12H11BrN2O
3-BROMO-2-(3-CHLOROPHENYL)PYRIDIN-4-AMINE 3-BROMO-2-(3-CHLOROPHENYL)PYRIDIN-4-AMINE 1381933-34-1 C11H8BrClN2
3-BROMO-2-(3-METHOXYPHENYL)PYRIDIN-4-AMINE 3-BROMO-2-(3-METHOXYPHENYL)PYRIDIN-4-AMINE 1381941-70-3 C12H11BrN2O
3-Bromo-2-(4-cyanophenyl)pyridine 3-Bromo-2-(4-cyanophenyl)pyridine 1563529-86-1 C12H7BrN2
3-BROMO-2-(4-METHYL-1H-IMIDAZOL-1-YL)PYRIDIN-4-AMINE 3-BROMO-2-(4-METHYL-1H-IMIDAZOL-1-YL)PYRIDIN-4-AMINE 1381933-61-4 C9H9BrN4
3-BROMO-2-(PIPERIDIN-1-YL)PYRIDIN-4-AMINE 3-BROMO-2-(PIPERIDIN-1-YL)PYRIDIN-4-AMINE 1381944-08-6 C10H14BrN3
3-BROMO-2-(PYRIDIN-4-YL)PYRIDIN-4-AMINE 3-BROMO-2-(PYRIDIN-4-YL)PYRIDIN-4-AMINE 1381943-64-1 C10H8BrN3
3-BROMO-2-CYCLOPENTYLPYRIDIN-4-AMINE 3-BROMO-2-CYCLOPENTYLPYRIDIN-4-AMINE 1381938-66-4 C10H13BrN2
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