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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-(Tetrahydrofuran-3-yl)pyridine 3-(Tetrahydrofuran-3-yl)pyridine 1434127-23-7 C9H11NO
3-(THIOPHEN-2-YL)PYRIDIN-4-AMINE 3-(THIOPHEN-2-YL)PYRIDIN-4-AMINE 1342778-18-0 C9H8N2S
3,4-Dibromo-2-(2-pyridyl)pyridine 3,4-Dibromo-2-(2-pyridyl)pyridine 1381943-49-2 C10H6Br2N2
3,4-Dibromo-2-(3-fluorophenyl)pyridine 3,4-Dibromo-2-(3-fluorophenyl)pyridine 1381943-54-9 C11H6Br2FN
3,4-Dibromo-2-(5-pyrimidyl)pyridine 3,4-Dibromo-2-(5-pyrimidyl)pyridine 1381942-92-2 C9H5Br2N3
3,4-Dibromo-2-(tert-butoxy)pyridine 3,4-Dibromo-2-(tert-butoxy)pyridine 1381942-39-7 C9H11Br2NO
3,4-Dibromo-6-(1H-pyrrol-1-yl)pyridine 3,4-Dibromo-6-(1H-pyrrol-1-yl)pyridine 1381934-01-5 C9H6Br2N2
3,4-Dibromo-6-(2-methoxyphenyl)pyridine 3,4-Dibromo-6-(2-methoxyphenyl)pyridine 1381941-38-3 C12H9Br2NO
3,4-Dibromo-6-(3-thienyl)pyridine 3,4-Dibromo-6-(3-thienyl)pyridine 1381941-26-9 C9H5Br2NS
3,4-Dibromo-6-(4-hydroxypiperidin-1-yl)pyridine 3,4-Dibromo-6-(4-hydroxypiperidin-1-yl)pyridine 1381943-83-4 C10H12Br2N2O
3,5-Dibromo-2-(2-tolyl)pyridine 3,5-Dibromo-2-(2-tolyl)pyridine 1399481-30-1 C12H9Br2N
3,5-Dibromo-6-(3-fluorophenyl)pyridine 3,5-Dibromo-6-(3-fluorophenyl)pyridine 1399482-07-5 C11H6Br2FN
3,5-Dibromo-6-(4-methoxyphenyl)pyridine 3,5-Dibromo-6-(4-methoxyphenyl)pyridine 1399482-14-4 C12H9Br2NO
3-AMINO-2-(4-METHYLIMIDAZOL-1-YL)PYRIDINE 3-AMINO-2-(4-METHYLIMIDAZOL-1-YL)PYRIDINE 1563533-50-5 C9H10N4
3-AMINO-4-(3-METHOXYPHENYL)PYRIDINE 3-AMINO-4-(3-METHOXYPHENYL)PYRIDINE 1368354-25-9 C12H12N2O
3-AMINO-4-(5-THIAZOLYL)PYRIDINE 3-AMINO-4-(5-THIAZOLYL)PYRIDINE 1369366-42-6 C8H7N3S
3-AMINO-5-(4-ETHYLPHENYL)PYRIDINE 3-AMINO-5-(4-ETHYLPHENYL)PYRIDINE 1226161-60-9 C13H14N2
3-AMINO-5-(4-THIAZOLYL)PYRIDINE 3-AMINO-5-(4-THIAZOLYL)PYRIDINE 1563532-81-9 C8H7N3S
3-Amino-5-(piperidin-3-yl)pyridine 3-Amino-5-(piperidin-3-yl)pyridine 1260640-76-3 C10H15N3
3-Amino-6-(4-methyl-1H-imidazol-1-yl)pyridazine 3-Amino-6-(4-methyl-1H-imidazol-1-yl)pyridazine 1314356-52-9 C8H9N5
3-BROMO-1-(PYRIMIDIN-2-YL)-1H-PYRAZOLE 3-BROMO-1-(PYRIMIDIN-2-YL)-1H-PYRAZOLE 1622840-19-0 C7H5BrN4
3-Bromo-2-(2-bromophenyl)pyridine 3-Bromo-2-(2-bromophenyl)pyridine 1312012-32-0 C11H7Br2N
3-Bromo-2-(2-fluorophenyl)pyridine 3-Bromo-2-(2-fluorophenyl)pyridine 1417519-78-8 C11H7BrFN
3-Bromo-2-(3-fluorophenyl)pyridine 3-Bromo-2-(3-fluorophenyl)pyridine 1417518-45-6 C11H7BrFN
3-BROMO-2-(4-CHLOROPHENYL)PYRIDIN-4-AMINE 3-BROMO-2-(4-CHLOROPHENYL)PYRIDIN-4-AMINE 1381938-41-5 C11H8BrClN2
3-BROMO-2-(4-FLUOROPHENYL)PYRIDIN-4-AMINE 3-BROMO-2-(4-FLUOROPHENYL)PYRIDIN-4-AMINE 1381938-31-3 C11H8BrFN2
3-BROMO-2-(FURAN-3-YL)PYRIDIN-4-AMINE 3-BROMO-2-(FURAN-3-YL)PYRIDIN-4-AMINE 1381942-05-7 C9H7BrN2O
3-Bromo-2-(n-propyl)pyridine 3-Bromo-2-(n-propyl)pyridine 1149593-25-8 C8H10BrN
3-BROMO-2-CYCLOBUTYLPYRIDIN-4-AMINE 3-BROMO-2-CYCLOBUTYLPYRIDIN-4-AMINE 1381941-66-7 C9H11BrN2
3-Bromo-4-(2-aminophenyl)pyridine 3-Bromo-4-(2-aminophenyl)pyridine 1563531-58-7 C11H9BrN2
3-Bromo-4-(2-furyl)pyridine 3-Bromo-4-(2-furyl)pyridine 1374664-81-9 C9H6BrNO
3-Bromo-4-(3-cyanophenyl)pyridine 3-Bromo-4-(3-cyanophenyl)pyridine 1563531-78-1 C12H7BrN2
3-Bromo-4-(4-trifluoromethylphenyl)pyridine 3-Bromo-4-(4-trifluoromethylphenyl)pyridine 1374665-22-1 C12H7BrF3N
3-Bromo-4-(cyclopentoxy)pyridine 3-Bromo-4-(cyclopentoxy)pyridine 1289127-14-5 C10H12BrNO
3-Bromo-4-amino-6-(3-pyridyl)pyridine 3-Bromo-4-amino-6-(3-pyridyl)pyridine 1381935-11-0 C10H8BrN3
3-BROMO-4-CHLORO-5-METHYLPYRIDIN-2-AMINE 3-BROMO-4-CHLORO-5-METHYLPYRIDIN-2-AMINE 1417518-35-4 C6H6BrClN2
3-bromo-5-(1H-pyrazol-1-yl-d3)pyridine 3-bromo-5-(1H-pyrazol-1-yl-d3)pyridine 2256707-41-0 C8H6BrN3
3-bromo-5-(2-bromophenyl)pyridine-2,4,6-d3 3-bromo-5-(2-bromophenyl)pyridine-2,4,6-d3 2256711-63-2 C11H7Br2N
3-BROMO-5-(4-BROMOPHENYL)PYRIDINE 3-BROMO-5-(4-BROMOPHENYL)PYRIDINE 1379330-29-6 C11H7Br2N
3-Bromo-5-(4-tert-butylphenyl)pyridine 3-Bromo-5-(4-tert-butylphenyl)pyridine 1314356-74-5 C15H16BrN
3-Bromo-5-(N-Boc-piperidin-3-yl)pyridine 3-Bromo-5-(N-Boc-piperidin-3-yl)pyridine 1563534-92-8 C15H21BrN2O2
3-BROMO-6-(2-BROMOPHENYL)PYRIDINE 3-BROMO-6-(2-BROMOPHENYL)PYRIDINE 1064057-73-3 C11H7Br2N
3-Bromo-6-(3,5-difluorophenyl)pyridine 3-Bromo-6-(3,5-difluorophenyl)pyridine 1215074-25-1 C11H6BrF2N
3-Bromo-6-(3-methyl-1H-pyrazol-1-yl)pyridine 3-Bromo-6-(3-methyl-1H-pyrazol-1-yl)pyridine 1215073-39-4 C9H8BrN3
3-Chloro-5-(piperidin-4-yl)pyridine 3-Chloro-5-(piperidin-4-yl)pyridine 1256794-67-8 C10H13ClN2
3-cyclobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one 3-cyclobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one 2256755-01-6 C15H22BNO3
3-ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one 3-ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one 2256755-03-8 C13H20BNO3
3-Hydroxy-2-(3-methoxyphenyl)pyridine 3-Hydroxy-2-(3-methoxyphenyl)pyridine 857436-14-7 C12H11NO2
3-Hydroxy-2,4'-bipyridine 3-Hydroxy-2,4'-bipyridine 103851-73-6 C10H8N2O
3-Hydroxy-5-(2-chlorophenyl)pyridine 3-Hydroxy-5-(2-chlorophenyl)pyridine 1258634-37-5 C11H8ClNO
3-Hydroxy-5-(3-furyl)pyridine 3-Hydroxy-5-(3-furyl)pyridine 1314355-57-1 C9H7NO2
3-Hydroxy-5-(3-tolyl)pyridine 3-Hydroxy-5-(3-tolyl)pyridine 1261931-22-9 C12H11NO
3-Hydroxy-5-(cyclobutoxy)pyridine 3-Hydroxy-5-(cyclobutoxy)pyridine 1314356-80-3 C9H11NO2
3-Hydroxy-5-(imidazol-1-yl)pyridine 3-Hydroxy-5-(imidazol-1-yl)pyridine 1314355-03-7 C8H7N3O
3-Hydroxy-6-(2-trifluoromethylphenyl)pyridine 3-Hydroxy-6-(2-trifluoromethylphenyl)pyridine 1261442-72-1 C12H8F3NO
3-Hydroxy-6-(5-pyrimidyl)pyridine 3-Hydroxy-6-(5-pyrimidyl)pyridine 1314356-63-2 C9H7N3O
4-(2-Aminophenyl)thiazole 4-(2-Aminophenyl)thiazole 1215071-73-0 C9H8N2S
4-(2-bromo-4-cyclopropylphenyl)morpholine 4-(2-bromo-4-cyclopropylphenyl)morpholine 2222935-47-7 C13H16BrNO
4-(2-BROMOPHENYL)PYRIDIN-3-AMINE 4-(2-BROMOPHENYL)PYRIDIN-3-AMINE 1368226-58-7 C11H9BrN2
4-(2-BROMOPYRIDIN-3-YL)BENZONITRILE 4-(2-BROMOPYRIDIN-3-YL)BENZONITRILE 1563532-68-2 C12H7BrN2
4-(3-bromo-4-cyclopropylphenyl)morpholine 4-(3-bromo-4-cyclopropylphenyl)morpholine 2222937-55-3 C13H16BrNO
4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazol-1-yl)thiazole 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-1,2,3-triazol-1-yl)thiazole 2256757-90-9 C11H15BN4O2S
4-(4-AMINOPHENYL)PYRIDIN-3-AMINE 4-(4-AMINOPHENYL)PYRIDIN-3-AMINE 1563530-17-5 C11H11N3
4-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256706-70-2 C14H15BBrD2N3O2
4-(5-AMINOPYRIDIN-2-YL)BENZONITRILE 4-(5-AMINOPYRIDIN-2-YL)BENZONITRILE 1072448-09-9 C12H9N3
4-(ethoxy-d5)pyridin-3-amine 4-(ethoxy-d5)pyridin-3-amine 2259316-14-6 C7H10N2O
4-(methyl-d3)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-3,5-d2)pyridine-3,5,6-d3 4-(methyl-d3)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-3,5-d2)pyridine-3,5,6-d3 2256706-30-4 C15H20BN3O2
4-(methyl-d3)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-3,5-d2)pyridine-2,5,6-d3 4-(methyl-d3)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-3,5-d2)pyridine-2,5,6-d3 2256706-24-6 C15H12BD8N3O2
4-(propoxy-d7)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 4-(propoxy-d7)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 2241874-74-6 C14H22BNO3
4-(tetrahydro-2H-pyran-3-yl)pyridin-2-ol 4-(tetrahydro-2H-pyran-3-yl)pyridin-2-ol 2222934-61-2 C10H13NO2
4,5-Dibromo-2-(2-furyl)thiazole 4,5-Dibromo-2-(2-furyl)thiazole 1314354-44-3 C7H3Br2NOS
4,5-Dibromo-2-(2-thienyl)thiazole 4,5-Dibromo-2-(2-thienyl)thiazole 1314355-28-6 C7H3Br2NS2
4,5-Dibromo-2-(4-fluorophenyl)thiazole 4,5-Dibromo-2-(4-fluorophenyl)thiazole 1314355-25-3 C9H4Br2FNS
4,5-Dibromo-2-(4-pyridyl)thiazole 4,5-Dibromo-2-(4-pyridyl)thiazole 1314357-35-1 C8H4Br2N2S
4,5-Dibromo-2-(cyclopropyl)thiazole 4,5-Dibromo-2-(cyclopropyl)thiazole 1314353-85-9 C6H5Br2NS
4,5-Dibromo-2-(iso-butyl)thiazole 4,5-Dibromo-2-(iso-butyl)thiazole 1643538-27-5 C7H9Br2NS
4,5-Dibromo-2-(pyrrolidino)thiazole 4,5-Dibromo-2-(pyrrolidino)thiazole 1314357-39-5 C7H8Br2N2S
4,5-Dibromo-2-ethylthiazole 4,5-Dibromo-2-ethylthiazole 120258-48-2 C5H5Br2NS
4-Amino-1-(2-chloro-4-pyridyl)imidazole 4-Amino-1-(2-chloro-4-pyridyl)imidazole 1353854-22-4 C8H7ClN4
4-Amino-1-(2-methyl-4-pyridyl)imidazole 4-Amino-1-(2-methyl-4-pyridyl)imidazole 1353855-43-2 C9H10N4
4-Amino-2-(2-chlorophenyl)thiazole 4-Amino-2-(2-chlorophenyl)thiazole 1353855-25-0 C9H7ClN2S
4-Amino-2-(4-ethylphenyl)thiazole 4-Amino-2-(4-ethylphenyl)thiazole 1159820-20-8 C11H12N2S
4-Amino-2-(tetrahydrofuran-3-yl)pyrimidine 4-Amino-2-(tetrahydrofuran-3-yl)pyrimidine 1159814-20-6 C8H11N3O
4-Amino-2,6-diphenylpyrimidine 4-Amino-2,6-diphenylpyrimidine 41270-99-9 C16H13N3
4-Amino-2-chloro-3-bromo-5-(3-methoxyphenyl)pyridine 4-Amino-2-chloro-3-bromo-5-(3-methoxyphenyl)pyridine 1563528-66-4 C12H10BrClN2O
4-Amino-2-chloro-3-bromo-5,3'-bipyridine 4-Amino-2-chloro-3-bromo-5,3'-bipyridine 1563533-67-4 C10H7BrClN3
4-Amino-2-phenyl-6-cyclopropylpyrimidine 4-Amino-2-phenyl-6-cyclopropylpyrimidine 1159819-75-6 C13H13N3
4-AMINO-3-(CYCLOHEXYLOXY)PYRIDINE 4-AMINO-3-(CYCLOHEXYLOXY)PYRIDINE 1563534-06-4 C11H16N2O
4-Amino-3-(oxan-2-yl)pyridine 4-Amino-3-(oxan-2-yl)pyridine 1622835-93-1 C10H14N2O
4-Amino-3,5-dibromo-2-(3-chlorophenyl)pyridine 4-Amino-3,5-dibromo-2-(3-chlorophenyl)pyridine 1563534-30-4 C11H7Br2ClN2
4-Amino-3,5-dibromo-2-(4-methylimidazol-1-yl)pyridine 4-Amino-3,5-dibromo-2-(4-methylimidazol-1-yl)pyridine 1563530-21-1 C9H8Br2N4
4-Amino-3,5-dibromo-2-(cyclobutoxy)pyridine 4-Amino-3,5-dibromo-2-(cyclobutoxy)pyridine 1563531-81-6 C9H10Br2N2O
4-Amino-3,5-dibromo-2-(pyrimidin-5-yl)pyridine 4-Amino-3,5-dibromo-2-(pyrimidin-5-yl)pyridine 1563532-62-6 C9H6Br2N4
4-Amino-3,5-dibromo-2-(thiazol-5-yl)pyridine 4-Amino-3,5-dibromo-2-(thiazol-5-yl)pyridine 1563529-16-7 C8H5Br2N3S
4-Amino-3-bromo-2-(3,5-difluorophenyl)pyridine 4-Amino-3-bromo-2-(3,5-difluorophenyl)pyridine 1563534-64-4 C11H7BrF2N2
4-Amino-3-bromo-6-(3,5-difluorophenyl)pyridine 4-Amino-3-bromo-6-(3,5-difluorophenyl)pyridine 1563530-27-7 C11H7BrF2N2
4-Amino-3-bromo-6-(4-trifluoromethylphenyl)pyridine 4-Amino-3-bromo-6-(4-trifluoromethylphenyl)pyridine 1381933-71-6 C12H8BrF3N2
4-Amino-5-bromo-2-(iso-butyl)pyrimidine 4-Amino-5-bromo-2-(iso-butyl)pyrimidine 1500625-21-7 C8H12BrN3
4-Amino-6-(2-methylpiperidin-1-yl)pyrimidine 4-Amino-6-(2-methylpiperidin-1-yl)pyrimidine 1314353-57-5 C10H16N4
4-Amino-6-(2-trifluoromethylphenyl)-2-cyclopropylpyrimidine 4-Amino-6-(2-trifluoromethylphenyl)-2-cyclopropylpyrimidine 1159819-82-5 C14H12F3N3
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