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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-AMINO-4-(3,5-DIFLUOROPHENYL)PYRIDINE 3-AMINO-4-(3,5-DIFLUOROPHENYL)PYRIDINE 1374665-04-9 C11H8F2N2
3-AMINO-4-(3-THIENYL)PYRIDINE 3-AMINO-4-(3-THIENYL)PYRIDINE 1048960-63-9 C9H8N2S
3-AMINO-4-(PYRROLIDINO)PYRIDINE 3-AMINO-4-(PYRROLIDINO)PYRIDINE 90648-19-4 C9H13N3
3-AMINO-5-(4-METHYLIMIDAZOL-1-YL)PYRIDINE 3-AMINO-5-(4-METHYLIMIDAZOL-1-YL)PYRIDINE 1314353-73-5 C9H10N4
3-AMINO-5-(CYCLOBUTOXY)PYRIDINE 3-AMINO-5-(CYCLOBUTOXY)PYRIDINE 1314356-81-4 C9H12N2O
3-Amino-5-(tetrahydrofuran-3-yloxy)pyridine 3-Amino-5-(tetrahydrofuran-3-yloxy)pyridine 1563534-47-3 C9H12N2O2
3-Amino-5-bromo-6-(2-pyridyl)pyridine 3-Amino-5-bromo-6-(2-pyridyl)pyridine 1399481-75-4 C10H8BrN3
3-Amino-5-bromo-6-(4-trifluoromethylphenyl)pyridine 3-Amino-5-bromo-6-(4-trifluoromethylphenyl)pyridine 1399481-88-9 C12H8BrF3N2
3-AMINO-5-CYCLOHEXYLPYRIDINE 3-AMINO-5-CYCLOHEXYLPYRIDINE 1314356-20-1 C11H16N2
3-AMINO-6-(2-TETRAHYDROPYRANYL)PYRIDAZINE 3-AMINO-6-(2-TETRAHYDROPYRANYL)PYRIDAZINE 1622835-38-4 C9H13N3O
3-BROMO-2-(1H-IMIDAZOL-1-YL)PYRIDIN-4-AMINE 3-BROMO-2-(1H-IMIDAZOL-1-YL)PYRIDIN-4-AMINE 1381935-78-9 C8H7BrN4
3-Bromo-2-(2-methoxyphenyl)pyridine 3-Bromo-2-(2-methoxyphenyl)pyridine 1171900-44-9 C12H10BrNO
3-Bromo-2-(2-methylpiperidin-1-yl)pyridine 3-Bromo-2-(2-methylpiperidin-1-yl)pyridine 1248602-34-7 C11H15BrN2
3-Bromo-2-(3-methoxyphenyl)pyridine 3-Bromo-2-(3-methoxyphenyl)pyridine 1417519-81-3 C12H10BrNO
3-Bromo-2-(3-methylpiperidin-1-yl)pyridine 3-Bromo-2-(3-methylpiperidin-1-yl)pyridine 1247632-81-0 C11H15BrN2
3-BROMO-2-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDIN-4-AMINE 3-BROMO-2-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDIN-4-AMINE 1381941-50-9 C9H9BrN4
3-Bromo-2-(4-tetrahydropyranyl)pyridine 3-Bromo-2-(4-tetrahydropyranyl)pyridine 1417519-31-3 C10H12BrNO
3-Bromo-2-(piperidin-3-yl)pyridine 3-Bromo-2-(piperidin-3-yl)pyridine 1260647-25-3 C10H13BrN2
3-BROMO-2-(PYRIMIDIN-5-YL)PYRIDIN-4-AMINE 3-BROMO-2-(PYRIMIDIN-5-YL)PYRIDIN-4-AMINE 1381943-65-2 C9H7BrN4
3-BROMO-2-CYCLOPROPYLPYRIDIN-4-AMINE 3-BROMO-2-CYCLOPROPYLPYRIDIN-4-AMINE 1381938-58-4 C8H9BrN2
3-bromo-2-fluoro-6-(methyl-d3)pyridine-4,5-d2 3-bromo-2-fluoro-6-(methyl-d3)pyridine-4,5-d2 2294950-38-0 C6H5BrFN
3-BROMO-4-(2-METHYLIMIDAZOL-1-YL)PYRIDINE 3-BROMO-4-(2-METHYLIMIDAZOL-1-YL)PYRIDINE 1289128-28-4 C9H8BrN3
3-Bromo-4-(2-tolyl)pyridine 3-Bromo-4-(2-tolyl)pyridine 88345-87-3 C12H10BrN
3-BROMO-4-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 3-BROMO-4-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 1289081-90-8 C9H8BrN3
3-Bromo-4-(pyrazol-4-yl)pyridine 3-Bromo-4-(pyrazol-4-yl)pyridine 1563528-91-5 C8H6BrN3
3-Bromo-4-methyl-1-(cyclopropyl)-1H-pyrazole 3-Bromo-4-methyl-1-(cyclopropyl)-1H-pyrazole 1563532-45-5 C7H9BrN2
3-Bromo-5-(2-methylpiperidin-1-yl)pyridine 3-Bromo-5-(2-methylpiperidin-1-yl)pyridine 1289153-40-7 C11H15BrN2
3-bromo-5-(3-bromophenyl)pyridine-2,4,6-d3 3-bromo-5-(3-bromophenyl)pyridine-2,4,6-d3 2256712-00-0 C11H7Br2N
3-Bromo-5-(-5-aminopyrazin-2-yl)pyridine 3-Bromo-5-(-5-aminopyrazin-2-yl)pyridine 1412955-47-5 C9H7BrN4
3-Bromo-5-(diethylamino)pyridine 3-Bromo-5-(diethylamino)pyridine 1255957-53-9 C9H13BrN2
3-Bromo-5-(thiazol-2-yl)pyridine 3-Bromo-5-(thiazol-2-yl)pyridine 1211531-23-5 C8H5BrN2S
3-Bromo-6-(3-furyl)pyridine 3-Bromo-6-(3-furyl)pyridine 1159820-83-3 C9H6BrNO
3-CHLORO-6-(2-TETRAHYDROPYRANYL)PYRIDAZINE 3-CHLORO-6-(2-TETRAHYDROPYRANYL)PYRIDAZINE 1622835-76-0 C9H11ClN2O
3-chloro-6-(tetrahydrofuran-2-yl)pyridazine 3-chloro-6-(tetrahydrofuran-2-yl)pyridazine 1872790-45-8 C8H9ClN2O
3-Hydroxy-2-(3-trifluoromethylphenyl)pyridine 3-Hydroxy-2-(3-trifluoromethylphenyl)pyridine 1261772-92-2 C12H8F3NO
3-Hydroxy-2-(4-trifluoromethylphenyl)pyridine 3-Hydroxy-2-(4-trifluoromethylphenyl)pyridine 1261886-11-6 C12H8F3NO
3-Hydroxy-5-(2-methoxyphenyl)pyridine 3-Hydroxy-5-(2-methoxyphenyl)pyridine 1261971-94-1 C12H11NO2
3-Hydroxy-5-(2-thienyl)pyridine 3-Hydroxy-5-(2-thienyl)pyridine 1261956-35-7 C9H7NOS
3-Hydroxy-5-(4-chlorophenyl)pyridine 3-Hydroxy-5-(4-chlorophenyl)pyridine 1258631-99-0 C11H8ClNO
3-Hydroxy-5-(4-methylpiperidin-1-yl)pyridine 3-Hydroxy-5-(4-methylpiperidin-1-yl)pyridine 1314356-94-9 C11H16N2O
3-Hydroxy-5-(pyrrolidino)pyridine 3-Hydroxy-5-(pyrrolidino)pyridine 1314356-82-5 C9H12N2O
3-iodopyridine-2,4,5,6-d4 3-iodopyridine-2,4,5,6-d4 2259315-96-1 C5H4IN
4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl-3,5,6-d3)morpholine-2,2,3,3,5,5,6,6-d8 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl-3,5,6-d3)morpholine-2,2,3,3,5,5,6,6-d8 2241874-79-1 C15H23BN2O3
4-(2-FLUOROPHENYL)PYRIDIN-3-AMINE 4-(2-FLUOROPHENYL)PYRIDIN-3-AMINE 146141-00-6 C11H9FN2
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazole 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazole 2256756-31-5 C15H17BF3N3O2
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(o-tolyl)-1H-1,2,3-triazole 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(o-tolyl)-1H-1,2,3-triazole 2256756-23-5 C15H20BN3O2
4-(4-bromo-1H-imidazol-1-yl-2,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 4-(4-bromo-1H-imidazol-1-yl-2,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 2256706-68-8 C14H17BBrN3O2
4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl-2,4,6-d3)morpholine-2,2,3,3,5,5,6,6-d8 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl-2,4,6-d3)morpholine-2,2,3,3,5,5,6,6-d8 2241869-87-2 C15H23BN2O3
4-(ethoxy-d5)pyridin-2,5,6-d3-3-amine 4-(ethoxy-d5)pyridin-2,5,6-d3-3-amine 2259316-20-4 C7H10N2O
4-(ISO-BUTYL)PYRIDIN-3-AMINE 4-(ISO-BUTYL)PYRIDIN-3-AMINE 1369340-77-1 C9H14N2
4-(tetrahydro-2H-pyran-2-yl)pyrimidin-2-amine 4-(tetrahydro-2H-pyran-2-yl)pyrimidin-2-amine 1622836-19-4 C9H13N3O
4-(tetrahydrofuran-3-yl)pyridin-2-ol 4-(tetrahydrofuran-3-yl)pyridin-2-ol 2222934-50-9 C9H11NO2
4,5-Dibromo-1-cyclohexyl-2-(iso-propyl)-1H-imidazole 4,5-Dibromo-1-cyclohexyl-2-(iso-propyl)-1H-imidazole 1622839-11-5 C12H18Br2N2
4,5-Dibromo-2-(3-chlorophenyl)thiazole 4,5-Dibromo-2-(3-chlorophenyl)thiazole 1314353-89-3 C9H4Br2ClNS
4,5-Dibromo-2-(4-trifluoromethylphenyl)thiazole 4,5-Dibromo-2-(4-trifluoromethylphenyl)thiazole 1314357-33-9 C10H4Br2F3NS
4,5-Dibromo-2-(cyclohexyl)pyrimidine 4,5-Dibromo-2-(cyclohexyl)pyrimidine 1563535-10-3 C10H12Br2N2
4,5-Dibromo-2-(iso-propyl)thiazole 4,5-Dibromo-2-(iso-propyl)thiazole 1314355-93-5 C6H7Br2NS
4-Amino-1-(5-cyclopropyl-3-pyridyl)imidazole 4-Amino-1-(5-cyclopropyl-3-pyridyl)imidazole 1353854-36-0 C11H12N4
4-Amino-2-(3-aminophenyl)pyridine 4-Amino-2-(3-aminophenyl)pyridine 1215072-99-3 C11H11N3
4-Amino-2-(4-aminophenyl)pyrimidine 4-Amino-2-(4-aminophenyl)pyrimidine 1339380-18-5 C10H10N4
4-Amino-2-(4-tert-butylphenyl)thiazole 4-Amino-2-(4-tert-butylphenyl)thiazole 123970-70-7 C13H16N2S
4-Amino-2-chloro-3-bromo-5-(2-fluorophenyl)pyridine 4-Amino-2-chloro-3-bromo-5-(2-fluorophenyl)pyridine 1563528-64-2 C11H7BrClFN2
4-Amino-2-chloro-3-bromo-5-(2-trifluoromethylphenyl)pyridine 4-Amino-2-chloro-3-bromo-5-(2-trifluoromethylphenyl)pyridine 1563534-73-5 C12H7BrClF3N2
4-Amino-2-chloro-3-bromo-5-(4-methoxyphenyl)pyridine 4-Amino-2-chloro-3-bromo-5-(4-methoxyphenyl)pyridine 1563528-68-6 C12H10BrClN2O
4-Amino-2-chloro-3-bromo-5-(cyclopropyl)pyridine 4-Amino-2-chloro-3-bromo-5-(cyclopropyl)pyridine 1563533-20-9 C8H8BrClN2
4-Amino-2-methyl-6-(2-methyl-5-thiazolyl)pyrimidine 4-Amino-2-methyl-6-(2-methyl-5-thiazolyl)pyrimidine 1159819-18-7 C9H10N4S
4-Amino-2-methyl-6-(4-pyridyl)pyrimidine 4-Amino-2-methyl-6-(4-pyridyl)pyrimidine 1159818-03-7 C10H10N4
4-AMINO-3-(2-FURYL)PYRIDINE 4-AMINO-3-(2-FURYL)PYRIDINE 1339414-96-8 C9H8N2O
4-AMINO-3-(IMIDAZOL-1-YL)PYRIDINE 4-AMINO-3-(IMIDAZOL-1-YL)PYRIDINE 1563533-45-8 C8H8N4
4-Amino-3-(tetrahydrofuran-3-yloxy)pyridine 4-Amino-3-(tetrahydrofuran-3-yloxy)pyridine 1563530-88-0 C9H12N2O2
4-Amino-3,5-dibromo-2-(3,4-difluorophenyl)pyridine 4-Amino-3,5-dibromo-2-(3,4-difluorophenyl)pyridine 1563532-31-9 C11H6Br2F2N2
4-Amino-3,5-dibromo-2-(3-furyl)pyridine 4-Amino-3,5-dibromo-2-(3-furyl)pyridine 1563532-53-5 C9H6Br2N2O
4-Amino-3,5-dibromo-2-(4-tolyl)pyridine 4-Amino-3,5-dibromo-2-(4-tolyl)pyridine 1563530-14-2 C12H10Br2N2
4-Amino-3,5-dibromo-2-(tert-butyl)pyridine 4-Amino-3,5-dibromo-2-(tert-butyl)pyridine 1563529-52-1 C9H12Br2N2
4-Amino-3,5-dibromo-2,4'-bipyridine 4-Amino-3,5-dibromo-2,4'-bipyridine 1563534-00-8 C10H7Br2N3
4-Amino-3-bromo-2-(4-cyanophenyl)pyridine 4-Amino-3-bromo-2-(4-cyanophenyl)pyridine 1622839-08-0 C12H8BrN3
4-Amino-3-bromo-2-(ethylmethylamino)pyridine 4-Amino-3-bromo-2-(ethylmethylamino)pyridine 1563529-71-4 C8H12BrN3
4-Amino-3-bromo-6-(3-trifluoromethylphenyl)pyridine 4-Amino-3-bromo-6-(3-trifluoromethylphenyl)pyridine 1381935-39-2 C12H8BrF3N2
4-Amino-3-bromo-6-(cyclopentoxy)pyridine 4-Amino-3-bromo-6-(cyclopentoxy)pyridine 1446412-83-4 C10H13BrN2O
4-Amino-5-bromo-2-(sec-butyl)pyrimidine 4-Amino-5-bromo-2-(sec-butyl)pyrimidine 1503643-72-8 C8H12BrN3
4-Brom-6-(2-methylpiperidin-1-yl)pyrimidine 4-Brom-6-(2-methylpiperidin-1-yl)pyrimidine 1314356-60-9 C10H14BrN3
4-Bromo-1-(2-amino-3-bromo-4-pyridyl)pyrazole 4-Bromo-1-(2-amino-3-bromo-4-pyridyl)pyrazole 1357580-37-0 C8H6Br2N4
4-Bromo-1-(2-methoxy-4-pyridyl)pyrazole 4-Bromo-1-(2-methoxy-4-pyridyl)pyrazole 1353854-12-2 C9H8BrN3O
4-Bromo-1-(2-methyl-4-pyridyl)imidazole 4-Bromo-1-(2-methyl-4-pyridyl)imidazole 1353854-25-7 C9H8BrN3
4-Bromo-1-(6-amino-2-pyridyl)pyrazole 4-Bromo-1-(6-amino-2-pyridyl)pyrazole 1363253-83-1 C8H7BrN4
4-Bromo-1-(oxan-2-yl)-2-ethylimidazole 4-Bromo-1-(oxan-2-yl)-2-ethylimidazole 1622835-56-6 C10H15BrN2O
4-Bromo-1-(propan-2-yl)-1H-1,2,3-triazole 4-Bromo-1-(propan-2-yl)-1H-1,2,3-triazole 1260667-92-2 C5H8BrN3
4-Bromo-2-(2-cyanophenyl)pyridine 4-Bromo-2-(2-cyanophenyl)pyridine 1563532-61-5 C12H7BrN2
4-Bromo-2-(2-thienyl)thiazole 4-Bromo-2-(2-thienyl)thiazole 1142194-93-1 C7H4BrNS2
4-Bromo-2-(3-chlorophenyl)pyridine 4-Bromo-2-(3-chlorophenyl)pyridine 1374665-30-1 C11H7BrClN
4-Bromo-2-(3-fluorophenyl)thiazole 4-Bromo-2-(3-fluorophenyl)thiazole 1142196-37-9 C9H5BrFNS
4-Bromo-2-(3-methoxyphenyl)pyridine 4-Bromo-2-(3-methoxyphenyl)pyridine 1215072-68-6 C12H10BrNO
4-Bromo-2-(3-tolyl)thiazole 4-Bromo-2-(3-tolyl)thiazole 1142196-29-9 C10H8BrNS
4-Bromo-2-(4-tert-butylphenyl)thiazole 4-Bromo-2-(4-tert-butylphenyl)thiazole 1142196-51-7 C13H14BrNS
4-Bromo-2-(iso-butyl)pyridine 4-Bromo-2-(iso-butyl)pyridine 1563532-13-7 C9H12BrN
4-Bromo-2-(pyrrolidinon-1-yl)thiazole 4-Bromo-2-(pyrrolidinon-1-yl)thiazole 1086381-67-0 C7H7BrN2OS
4-Bromo-2-cyclobutylthiazole 4-Bromo-2-cyclobutylthiazole 1142196-22-2 C7H8BrNS
4-Bromo-2-hydroxy-5-(cyclopropyl)pyrimidine 4-Bromo-2-hydroxy-5-(cyclopropyl)pyrimidine 1381934-58-2 C7H7BrN2O
4-bromo-3-(1H-pyrazol-1-yl-d3)pyridine 4-bromo-3-(1H-pyrazol-1-yl-d3)pyridine 2256707-39-6 C8H6BrN3
4-Bromo-3-(2-chlorophenyl)pyridine 4-Bromo-3-(2-chlorophenyl)pyridine 1374665-88-9 C11H7BrClN
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