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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-(2-cyclopropylpyrimidyl-5-yl)thiazole 2-Bromo-4-(2-cyclopropylpyrimidyl-5-yl)thiazole 1215072-04-0 C10H8BrN3S
2-Bromo-4-(2-furyl)pyridine 2-Bromo-4-(2-furyl)pyridine 1086381-49-8 C9H6BrNO
2-Bromo-4-(2-thiazolyl)furan 2-Bromo-4-(2-thiazolyl)furan 1159815-26-5 C7H4BrNOS
2-Bromo-4-(2-tolyl)furan 2-Bromo-4-(2-tolyl)furan 1159817-19-2 C11H9BrO
2-Bromo-4-(3-cyanophenyl)pyridine 2-Bromo-4-(3-cyanophenyl)pyridine 1563532-82-0 C12H7BrN2
2-Bromo-4-(4-fluorophenyl)thiophene 2-Bromo-4-(4-fluorophenyl)thiophene 1159818-44-6 C10H6BrFS
2-Bromo-4-(4-methoxyphenyl)thiophene 2-Bromo-4-(4-methoxyphenyl)thiophene 1159820-52-6 C11H9BrOS
2-Bromo-4-(5-thiazolyl)pyridine 2-Bromo-4-(5-thiazolyl)pyridine 1353855-57-8 C8H5BrN2S
2-Bromo-4-(cyclobutyl)thiophene 2-Bromo-4-(cyclobutyl)thiophene 1159815-82-3 C8H9BrS
2-Bromo-4-(methylethylamino)pyridine 2-Bromo-4-(methylethylamino)pyridine 937254-63-2 C8H11BrN2
2-BROMO-4-(PIPERIDIN-3-YL)PYRIMIDINE 2-BROMO-4-(PIPERIDIN-3-YL)PYRIMIDINE 1622834-94-9 C9H12BrN3
2-Bromo-4-(tert-butoxy)pyrimidine 2-Bromo-4-(tert-butoxy)pyrimidine 1209458-60-5 C8H11BrN2O
2-Bromo-4-amino-5-(3,4-difluorophenyl)pyridine 2-Bromo-4-amino-5-(3,4-difluorophenyl)pyridine 1381936-09-9 C11H7BrF2N2
2-Bromo-4-amino-5-(3-thienyl)pyridine 2-Bromo-4-amino-5-(3-thienyl)pyridine 1381944-03-1 C9H7BrN2S
2-bromo-4-chloro-3-(methyl-d3)pyridine-5,6-d2 2-bromo-4-chloro-3-(methyl-d3)pyridine-5,6-d2 2294946-73-7 C6H5BrClN
2-Bromo-4-chloro-6-(cyclopentyl)pyrimidine 2-Bromo-4-chloro-6-(cyclopentyl)pyrimidine 1434128-27-4 C9H10BrClN2
2-Bromo-4-chloro-6-(sec-butyl)pyrimidine 2-Bromo-4-chloro-6-(sec-butyl)pyrimidine 1434127-93-1 C8H10BrClN2
2-Bromo-5-(2-chloro-4-pyridyl)pyridine 2-Bromo-5-(2-chloro-4-pyridyl)pyridine 1142193-97-2 C10H6BrClN2
2-Bromo-5-(2-iso-propylpyrimidyl-5-yl)thiazole 2-Bromo-5-(2-iso-propylpyrimidyl-5-yl)thiazole 1215072-45-9 C10H10BrN3S
2-Bromo-5-(2-methoxyphenyl)thiophene 2-Bromo-5-(2-methoxyphenyl)thiophene 1159818-20-8 C11H9BrOS
2-Bromo-5-(2-tolyl)furan 2-Bromo-5-(2-tolyl)furan 1159821-93-8 C11H9BrO
2-Bromo-5-(2-trifluoromethylphenyl)furan 2-Bromo-5-(2-trifluoromethylphenyl)furan 1159818-31-1 C11H6BrF3O
2-Bromo-5-(3-fluorophenyl)pyridine 2-Bromo-5-(3-fluorophenyl)pyridine 1142197-39-4 C11H7BrFN
2-Bromo-5-(3-pyridyl)thiazole 2-Bromo-5-(3-pyridyl)thiazole 263868-72-0 C8H5BrN2S
2-Bromo-5-(3-tolyl)pyridine 2-Bromo-5-(3-tolyl)pyridine 1142197-34-9 C12H10BrN
2-Bromo-5-(4-fluorolphenyl)thiazole 2-Bromo-5-(4-fluorolphenyl)thiazole 1215073-10-1 C9H5BrFNS
2-Bromo-5-(4-methoxyphenyl)pyrimidine 2-Bromo-5-(4-methoxyphenyl)pyrimidine 1353856-57-1 C11H9BrN2O
2-Bromo-5-(5-pyrimidyl)pyridine 2-Bromo-5-(5-pyrimidyl)pyridine 475275-71-9 C9H6BrN3
2-Bromo-5-(cyclobutyl)thiophene 2-Bromo-5-(cyclobutyl)thiophene 1159815-85-6 C8H9BrS
2-Bromo-5-(sec-butyl)pyrimidine 2-Bromo-5-(sec-butyl)pyrimidine 1643542-12-4 C8H11BrN2
2-Bromo-5-amino-4-(2-furyl)pyridine 2-Bromo-5-amino-4-(2-furyl)pyridine 1381935-83-6 C9H7BrN2O
2-Bromo-5-amino-4-(3-methylpiperidin-1-yl)pyridine 2-Bromo-5-amino-4-(3-methylpiperidin-1-yl)pyridine 1381934-67-3 C11H16BrN3
2-Bromo-5-amino-4-(4-fluorophenyl)pyridine 2-Bromo-5-amino-4-(4-fluorophenyl)pyridine 1381942-51-3 C11H8BrFN2
2-Bromo-5-amino-4-phenylpyridine 2-Bromo-5-amino-4-phenylpyridine 1381934-36-6 C11H9BrN2
2-Bromo-6-(4-ethylphenyl)pyridine 2-Bromo-6-(4-ethylphenyl)pyridine 1142196-93-7 C13H12BrN
2-Bromo-6-(piperidin-4-yl)pyridine 2-Bromo-6-(piperidin-4-yl)pyridine 1159814-62-6 C10H13BrN2
2-Bromol-4-amino-5-(2-thienyl)pyrimidine 2-Bromol-4-amino-5-(2-thienyl)pyrimidine 1381934-69-5 C8H6BrN3S
2-Chloro-4-(2-chloro-4-thiazolyl)pyridine 2-Chloro-4-(2-chloro-4-thiazolyl)pyridine 1353855-97-6 C8H4Cl2N2S
2-Chloro-4-(2-furyl)-6-methoxy-1,3,5-triazine 2-Chloro-4-(2-furyl)-6-methoxy-1,3,5-triazine 1303967-77-2 C8H6ClN3O2
2-Chloro-4-(3,4-difluorophenyl)thiazole 2-Chloro-4-(3,4-difluorophenyl)thiazole 1188123-17-2 C9H4ClF2NS
2-Chloro-4-(3-furyl)-6-methoxy-1,3,5-triazine 2-Chloro-4-(3-furyl)-6-methoxy-1,3,5-triazine 1303967-54-5 C8H6ClN3O2
2-Chloro-4-(4-fluorophenyl)-6-methoxy-1,3,5-triazine 2-Chloro-4-(4-fluorophenyl)-6-methoxy-1,3,5-triazine 1303967-64-7 C10H7ClFN3O
2-Chloro-4-(tetrahydrofuran-3-yl)pyridine 2-Chloro-4-(tetrahydrofuran-3-yl)pyridine 1353856-84-4 C9H10ClNO
2-CHLORO-4-AMINO-3-(3-THIENYL)PYRIDINE 2-CHLORO-4-AMINO-3-(3-THIENYL)PYRIDINE 1381940-80-2 C9H7ClN2S
2-CHLORO-4-AMINO-3-(PIPERIDIN-4-YL)PYRIDINE 2-CHLORO-4-AMINO-3-(PIPERIDIN-4-YL)PYRIDINE 1563535-13-6 C10H14ClN3
2-Chloro-4-amino-5-(2-pyridyl)pyridine 2-Chloro-4-amino-5-(2-pyridyl)pyridine 1381942-24-0 C10H8ClN3
2-Chloro-4-amino-5-(4-tolyl)pyridine 2-Chloro-4-amino-5-(4-tolyl)pyridine 1381941-11-2 C12H11ClN2
2-Chloro-4-amino-5-(cyclopentyl)pyridine 2-Chloro-4-amino-5-(cyclopentyl)pyridine 1381936-01-1 C10H13ClN2
2-Chloro-4-amino-6-(3-fluorophenyl)pyrimidine 2-Chloro-4-amino-6-(3-fluorophenyl)pyrimidine 1353856-91-3 C10H7ClFN3
2-Chloro-4-amino-6-(3-trifluoromethylphenyl)pyrimidine 2-Chloro-4-amino-6-(3-trifluoromethylphenyl)pyrimidine 1353854-48-4 C11H7ClF3N3
2-Chloro-4-bromo-6-(2-furyl)pyrimidine 2-Chloro-4-bromo-6-(2-furyl)pyrimidine 1412954-31-4 C8H4BrClN2O
2-Chloro-4-bromo-6-(2-trifluoromethylphenyl)pyrimidine 2-Chloro-4-bromo-6-(2-trifluoromethylphenyl)pyrimidine 1412953-60-6 C11H5BrClF3N2
2-Chloro-4-bromo-6-(4-trifluoromethylphenyl)pyrimidine 2-Chloro-4-bromo-6-(4-trifluoromethylphenyl)pyrimidine 1412960-31-6 C11H5BrClF3N2
2-Chloro-4-bromo-6-(cyclobutyl)pyrimidine 2-Chloro-4-bromo-6-(cyclobutyl)pyrimidine 1412959-80-8 C8H8BrClN2
2-Chloro-4-bromo-6-phenylpyrimidine 2-Chloro-4-bromo-6-phenylpyrimidine 1412955-57-7 C10H6BrClN2
2-Chloro-4-cyclopentyl-6-hydroxy-1,3,5-triazine 2-Chloro-4-cyclopentyl-6-hydroxy-1,3,5-triazine 1303967-37-4 C8H10ClN3O
2-Chloro-5-(2-thienyl)pyrimidine 2-Chloro-5-(2-thienyl)pyrimidine 63558-67-8 C8H5ClN2S
2-Chloro-5-(4-methyl-1H-pyrazol-1-yl)pyrimidine 2-Chloro-5-(4-methyl-1H-pyrazol-1-yl)pyrimidine 1363253-82-0 C8H7ClN4
2-Chloro-5-(5-pyrimidyl)pyrimidine 2-Chloro-5-(5-pyrimidyl)pyrimidine 1363253-77-3 C8H5ClN4
2-Chloro-5-(piperidin-4-yl)pyrimidine 2-Chloro-5-(piperidin-4-yl)pyrimidine 1563529-61-2 C9H12ClN3
2-cyclohexyl-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-cyclohexyl-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2256758-21-9 C16H26BNO2S
2-Ethyl-4-hydroxythiazole 2-Ethyl-4-hydroxythiazole 1159816-91-7 C5H7NOS
2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-4,5,6-d3 2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-4,5,6-d3 2241870-42-6 C11H12BD3FNO2
2-fluoro-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl)pyridine 2-fluoro-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl)pyridine 2256755-50-5 C14H17BFN3O2
2-Hydroxy-3,4,5-tribromopyridine 2-Hydroxy-3,4,5-tribromopyridine 1399480-67-1 C5H2Br3NO
2-Hydroxy-4-(2-trifluoromethylphenyl)pyridine 2-Hydroxy-4-(2-trifluoromethylphenyl)pyridine 1215074-27-3 C12H8F3NO
2-Hydroxy-4-(3-fluorophenyl)thiophene 2-Hydroxy-4-(3-fluorophenyl)thiophene 1243839-21-5 C10H7FOS
2-Hydroxy-4-(4-trifluoromethylphenyl)pyridine 2-Hydroxy-4-(4-trifluoromethylphenyl)pyridine 942947-10-6 C12H8F3NO
2-Hydroxy-4-(cyclopentyl)pyridine 2-Hydroxy-4-(cyclopentyl)pyridine 1159820-48-0 C10H13NO
2-Hydroxy-5-(2-chlorophenyl)pyrimidine 2-Hydroxy-5-(2-chlorophenyl)pyrimidine 75175-35-8 C10H7ClN2O
2-Hydroxy-5-(2-fluorophenyl)pyrimidine 2-Hydroxy-5-(2-fluorophenyl)pyrimidine 1111103-52-6 C10H7FN2O
2-Hydroxy-5-(2-thienyl)pyridine 2-Hydroxy-5-(2-thienyl)pyridine 1111116-04-1 C9H7NOS
2-Hydroxy-5-(2-tolyl)thiophene 2-Hydroxy-5-(2-tolyl)thiophene 1243839-32-8 C11H10OS
2-Hydroxy-5-(3-furyl)pyridine 2-Hydroxy-5-(3-furyl)pyridine 1111115-91-3 C9H7NO2
2-Hydroxy-5-(3-methoxyphenyl)pyridine 2-Hydroxy-5-(3-methoxyphenyl)pyridine 76876-87-4 C12H11NO2
2-Hydroxy-5-(4-fluorolphenyl)thiazole 2-Hydroxy-5-(4-fluorolphenyl)thiazole 1215074-08-0 C9H6FNOS
2-Hydroxy-5-(cyclohexyl)pyrimidine 2-Hydroxy-5-(cyclohexyl)pyrimidine 90253-47-7 C10H14N2O
2-Hydroxy-5-(pyrimidyl-5-yl)thiazole 2-Hydroxy-5-(pyrimidyl-5-yl)thiazole 1215073-87-2 C7H5N3OS
2-Hydroxy-6-(2-trifluoromethylphenyl)-4-methylpyrimidine 2-Hydroxy-6-(2-trifluoromethylphenyl)-4-methylpyrimidine 1159819-00-7 C12H9F3N2O
2-Hydroxy-6-(3-thienyl)pyridine 2-Hydroxy-6-(3-thienyl)pyridine 1111114-72-7 C9H7NOS
2-Hydroxy-6-(5-pyrimidyl)pyrazine 2-Hydroxy-6-(5-pyrimidyl)pyrazine 1159814-92-2 C8H6N4O
3-(1H-pyrazol-1-yl-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 3-(1H-pyrazol-1-yl-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 2256709-85-8 C14H18BN3O2
3-(2-AMINOPHENYL)PYRIDIN-4-AMINE 3-(2-AMINOPHENYL)PYRIDIN-4-AMINE 1563530-78-8 C11H11N3
3-(2-bromophenyl)-5-(methyl-d3)pyridine-2,4,6-d3 3-(2-bromophenyl)-5-(methyl-d3)pyridine-2,4,6-d3 2256711-64-3 C12H10BrN
3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazol-1-yl)pyridazine 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazol-1-yl)pyridazine 2256757-96-5 C12H16BN5O2
3-(4-bromo-2-(methyl-d3)-1H-imidazol-1-yl-5-d)pyridine-2,4,5,6-d4 3-(4-bromo-2-(methyl-d3)-1H-imidazol-1-yl-5-d)pyridine-2,4,5,6-d4 2256710-06-0 C9H8BrN3
3-(4-bromophenyl)-6-(methyl-d3)pyridazine-4,5-d2 3-(4-bromophenyl)-6-(methyl-d3)pyridazine-4,5-d2 2256712-44-2 C11H9BrN2
3-(4-bromophenyl)pyridine-2,4,5,6-d4 3-(4-bromophenyl)pyridine-2,4,5,6-d4 2256711-92-7 C11H8BrN
3-(ethoxy-d5)pyridin-2,5,6-d3-4-amine 3-(ethoxy-d5)pyridin-2,5,6-d3-4-amine 2259316-24-8 C7H10N2O
3-(methyl-d3)-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl-2,5-d2)pyridine-2,4,6-d3 3-(methyl-d3)-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl-2,5-d2)pyridine-2,4,6-d3 2256706-44-0 C15H20BN3O2
3-(piperidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one 3-(piperidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one 2256754-98-8 C16H25BN2O3
3-(propan-2-yl-d7)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 3-(propan-2-yl-d7)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 2241875-07-8 C14H12BD10NO2
3,4-Dibromo-2-(3-methoxyphenyl)pyridine 3,4-Dibromo-2-(3-methoxyphenyl)pyridine 1381942-30-8 C12H9Br2NO
3,4-Dibromo-2-(3-tolyl)pyridine 3,4-Dibromo-2-(3-tolyl)pyridine 1381942-25-1 C12H9Br2N
3,4-Dibromo-2-(cyclopentyl)pyridine 3,4-Dibromo-2-(cyclopentyl)pyridine 1381943-44-7 C10H11Br2N
3,4-dibromo-2-(methyl-d3)pyridine 3,4-dibromo-2-(methyl-d3)pyridine 2294948-84-6 C6H5Br2N
3,4-Dibromo-6-(2-furyl)pyridine 3,4-Dibromo-6-(2-furyl)pyridine 1381943-79-8 C9H5Br2NO
3,4-Dibromo-6-(2-pyridyl)pyridine 3,4-Dibromo-6-(2-pyridyl)pyridine 1381937-22-9 C10H6Br2N2
3,4-Dibromo-6-(4-chlorophenyl)pyridine 3,4-Dibromo-6-(4-chlorophenyl)pyridine 1381935-15-4 C11H6Br2ClN
3,5-Dibromo-2-(2-pyridyl)pyridine 3,5-Dibromo-2-(2-pyridyl)pyridine 1399481-28-7 C10H6Br2N2
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