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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-Bromo-4-(2-chlorophenyl)pyridine 3-Bromo-4-(2-chlorophenyl)pyridine 1374665-48-1 C11H7BrClN
3-Bromo-4-(3-aminophenyl)pyridine 3-Bromo-4-(3-aminophenyl)pyridine 1563531-67-8 C11H9BrN2
3-BROMO-4-(3-HYDROXYPIPERIDIN-1-YL)PYRIDINE 3-BROMO-4-(3-HYDROXYPIPERIDIN-1-YL)PYRIDINE 1288994-79-5 C10H13BrN2O
3-BROMO-4-(4-TERT-BUTYLPHENYL)PYRIDINE 3-BROMO-4-(4-TERT-BUTYLPHENYL)PYRIDINE 1563529-13-4 C15H16BrN
3-Bromo-4-amino-6-(4-pyridyl)pyridine 3-Bromo-4-amino-6-(4-pyridyl)pyridine 1381941-19-0 C10H8BrN3
3-bromo-5-(1,4-dioxan-2-yl)pyridine 3-bromo-5-(1,4-dioxan-2-yl)pyridine 1434128-13-8 C9H10BrNO2
3-Bromo-5-(4-ethylphenyl)pyridine 3-Bromo-5-(4-ethylphenyl)pyridine 1246029-28-6 C13H12BrN
3-Bromo-5-(N-Boc-piperidin-4-yl)pyridine 3-Bromo-5-(N-Boc-piperidin-4-yl)pyridine 1206248-30-7 C15H21BrN2O2
3-Bromo-6-(2-methyl-4-fluorophenyl)pyridine 3-Bromo-6-(2-methyl-4-fluorophenyl)pyridine 1215071-92-3 C12H9BrFN
3-Bromo-6-(4-methyl-1H-pyrazol-1-yl)pyridine 3-Bromo-6-(4-methyl-1H-pyrazol-1-yl)pyridine 1215073-40-7 C9H8BrN3
3-Bromo-6-(cyclopentyl)pyridine 3-Bromo-6-(cyclopentyl)pyridine 1159820-60-6 C10H12BrN
3-Chloro-2-(oxan-2-yl)pyridine 3-Chloro-2-(oxan-2-yl)pyridine 1622834-63-2 C10H12ClNO
3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 2241874-93-9 C11H15BClNO2
3-CYCLOPROPYL-THIOPHENE 3-CYCLOPROPYL-THIOPHENE 29576-51-0 C7H8S
3-Hydroxy-2-(2-methoxyphenyl)pyridine 3-Hydroxy-2-(2-methoxyphenyl)pyridine 1261971-75-8 C12H11NO2
3-Hydroxy-2-(3,5-difluorophenyl)pyridine 3-Hydroxy-2-(3,5-difluorophenyl)pyridine 1261937-42-1 C11H7F2NO
3-Hydroxy-5-(1H-pyridin-2-one)pyridine 3-Hydroxy-5-(1H-pyridin-2-one)pyridine 1314353-74-6 C10H8N2O2
3-Hydroxy-5-(3-aminophenyl)pyridine 3-Hydroxy-5-(3-aminophenyl)pyridine 1261901-32-9 C11H10N2O
3-Hydroxy-5-(3-methyl-1H-pyrazol-1-yl)pyridine 3-Hydroxy-5-(3-methyl-1H-pyrazol-1-yl)pyridine 1314356-84-7 C9H9N3O
3-Hydroxy-5-(4-tolyl)pyridine 3-Hydroxy-5-(4-tolyl)pyridine 1261909-03-8 C12H11NO
3-Hydroxy-6-(2-furyl)pyridine 3-Hydroxy-6-(2-furyl)pyridine 1159821-12-1 C9H7NO2
3-Hydroxy-6-(3-thienyl)pyridine 3-Hydroxy-6-(3-thienyl)pyridine 1159820-76-4 C9H7NOS
4-(1H-imidazol-1-yl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(1H-imidazol-1-yl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256709-68-7 C14H18BN3O2
4-(2-bromophenyl)pyrimidine 4-(2-bromophenyl)pyrimidine 1781774-99-9 C10H7BrN2
4-(3-AMINOPHENYL)PYRIDIN-3-AMINE 4-(3-AMINOPHENYL)PYRIDIN-3-AMINE 1563531-72-5 C11H11N3
4-(3-Fluorophenyl)thiazole 4-(3-Fluorophenyl)thiazole 1215072-00-6 C9H6FNS
4-(4-(methyl-d3)-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-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 2256706-49-5 C15H20BN3O2
4-(4-bromo-2-cyclopropylphenyl)morpholine 4-(4-bromo-2-cyclopropylphenyl)morpholine 2222934-08-7 C13H16BrNO
4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl-2,4,5-d3)morpholine-2,2,3,3,5,5,6,6-d8 4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl-2,4,5-d3)morpholine-2,2,3,3,5,5,6,6-d8 2241867-71-8 C15H12BD11N2O3
4-(methoxy-d3)pyridin-3,5,6-d3-2-amine 4-(methoxy-d3)pyridin-3,5,6-d3-2-amine 2256707-59-0 C6H8N2O
4-(methyl-d3)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-4,5-d2)pyridine-3,5,6-d3 4-(methyl-d3)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-4,5-d2)pyridine-3,5,6-d3 2256705-85-6 C15H20BN3O2
4-(piperidin-1-yl-d10)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 4-(piperidin-1-yl-d10)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 2241874-80-4 C16H25BN2O2
4,5,6-Tribromopyrimidine 4,5,6-Tribromopyrimidine 1434128-24-1 C4HBr3N2
4,5-Dibromo-2-(3-tolyl)thiazole 4,5-Dibromo-2-(3-tolyl)thiazole 1314357-31-7 C10H7Br2NS
4,5-Dibromo-2-(cyclobutyl)thiazole 4,5-Dibromo-2-(cyclobutyl)thiazole 1314356-26-7 C7H7Br2NS
4,5-Dibromo-2-(cyclopentyl)pyrimidine 4,5-Dibromo-2-(cyclopentyl)pyrimidine 1563534-80-4 C9H10Br2N2
4,5-Dibromo-2-(morpholino)thiazole 4,5-Dibromo-2-(morpholino)thiazole 1314354-17-0 C7H8Br2N2OS
4,5-Dibromo-2-(n-propyl)thiazole 4,5-Dibromo-2-(n-propyl)thiazole 1314357-29-3 C6H7Br2NS
4,6-dibromopyrimidine-2,5-d2 4,6-dibromopyrimidine-2,5-d2 2241865-51-8 C4H2Br2N2
4-[2-(TRIFLUOROMETHYL)PHENYL]PYRIDIN-2-AMINE 4-[2-(TRIFLUOROMETHYL)PHENYL]PYRIDIN-2-AMINE 1215073-91-8 C12H9F3N2
4-Amino-1-(2-pyridyl)imidazole 4-Amino-1-(2-pyridyl)imidazole 1316122-52-7 C8H8N4
4-Amino-2-(2-aminophenyl)pyrimidine 4-Amino-2-(2-aminophenyl)pyrimidine 1622839-05-7 C10H10N4
4-Amino-2-(2-tolyl)pyrimidine 4-Amino-2-(2-tolyl)pyrimidine 1248805-62-0 C11H11N3
4-Amino-2-(3-cyanophenyl)pyridine 4-Amino-2-(3-cyanophenyl)pyridine 1556299-03-6 C12H9N3
4-Amino-2-(3-methoxyphenyl)thiazole 4-Amino-2-(3-methoxyphenyl)thiazole 123970-61-6 C10H10N2OS
4-Amino-2-(cyclohexenyl)thiazole 4-Amino-2-(cyclohexenyl)thiazole 1159815-79-8 C9H12N2S
4-Amino-2-(pyrrolidin-3-yl)pyrimidine 4-Amino-2-(pyrrolidin-3-yl)pyrimidine 1159821-21-2 C8H12N4
4-Amino-2-(tetrahyfuran-3-yl)thiazole 4-Amino-2-(tetrahyfuran-3-yl)thiazole 1159815-13-0 C7H10N2OS
4-Amino-2-chloro-3-bromo-5-(3-cyanophenyl)pyridine 4-Amino-2-chloro-3-bromo-5-(3-cyanophenyl)pyridine 1563534-56-4 C12H7BrClN3
4-Amino-2-chloro-3-bromo-5-(oxan-4-yl)pyridine 4-Amino-2-chloro-3-bromo-5-(oxan-4-yl)pyridine 1563529-12-3 C10H12BrClN2O
4-Amino-2-phenyl-6-(2-methyl-4-thiazolyl)pyrimidine 4-Amino-2-phenyl-6-(2-methyl-4-thiazolyl)pyrimidine 1159821-85-8 C14H12N4S
4-Amino-2-phenyl-6-(4-thiazolyl)pyrimidine 4-Amino-2-phenyl-6-(4-thiazolyl)pyrimidine 1159821-78-9 C13H10N4S
4-AMINO-3-(4-ETHYLPHENYL)PYRIDINE 4-AMINO-3-(4-ETHYLPHENYL)PYRIDINE 1340583-05-2 C13H14N2
4-AMINO-3-(4-THIAZOLYL)PYRIDINE 4-AMINO-3-(4-THIAZOLYL)PYRIDINE 1563532-88-6 C8H7N3S
4-Amino-3,5-dibromo-2-(2-methyl-4-fluorophenyl)pyridine 4-Amino-3,5-dibromo-2-(2-methyl-4-fluorophenyl)pyridine 1563532-34-2 C12H9Br2FN2
4-Amino-3,5-dibromo-2-(3-thienyl)pyridine 4-Amino-3,5-dibromo-2-(3-thienyl)pyridine 1563534-83-7 C9H6Br2N2S
4-Amino-3,5-dibromo-2-(4-fluorophenyl)pyridine 4-Amino-3,5-dibromo-2-(4-fluorophenyl)pyridine 1563533-86-7 C11H7Br2FN2
4-Amino-3,5-dibromo-2-(imidazol-1-yl)pyridine 4-Amino-3,5-dibromo-2-(imidazol-1-yl)pyridine 1563532-71-7 C8H6Br2N4
4-AMINO-3,5-DIBROMO-2-(N-PROPYL)PYRIDINE 4-AMINO-3,5-DIBROMO-2-(N-PROPYL)PYRIDINE 1563532-48-8 C8H10Br2N2
4-AMINO-3,5-DIBROMO-2-ETHYLPYRIDINE 4-AMINO-3,5-DIBROMO-2-ETHYLPYRIDINE 1563531-46-3 C7H8Br2N2
4-Amino-3-bromo-2-(2-hydroxypiperidin-1-yl)pyridine 4-Amino-3-bromo-2-(2-hydroxypiperidin-1-yl)pyridine 1381934-19-5 C10H14BrN3O
4-Amino-3-bromo-2-(sec-butyl)pyridine 4-Amino-3-bromo-2-(sec-butyl)pyridine 1563534-63-3 C9H13BrN2
4-Amino-3-bromo-6-(2-methoxyphenyl)pyridine 4-Amino-3-bromo-6-(2-methoxyphenyl)pyridine 1381943-57-2 C12H11BrN2O
4-Amino-3-bromo-6-(piperidin-4-yl)pyridine 4-Amino-3-bromo-6-(piperidin-4-yl)pyridine 1563532-43-3 C10H14BrN3
4-Amino-3-bromo-6-dimethylaminopyridine 4-Amino-3-bromo-6-dimethylaminopyridine 1446409-85-3 C7H10BrN3
4-Amino-6-(2-fluorophenyl)-2-cyclopropylpyrimidine 4-Amino-6-(2-fluorophenyl)-2-cyclopropylpyrimidine 1159821-29-0 C13H12FN3
4-Amino-6-(2-methoxyphenyl)pyrimidine 4-Amino-6-(2-methoxyphenyl)pyrimidine 1142004-97-4 C11H11N3O
4-Amino-6-(3-thienyl)pyrimidine 4-Amino-6-(3-thienyl)pyrimidine 1159818-42-4 C8H7N3S
4-Amino-6-(5-thiazolyl)-2-cyclopropylpyrimidine 4-Amino-6-(5-thiazolyl)-2-cyclopropylpyrimidine 1159822-00-0 C10H10N4S
4-Amino-6-phenyl-2-cyclopropylpyrimidine 4-Amino-6-phenyl-2-cyclopropylpyrimidine 1159815-74-3 C13H13N3
4-Bromo-1-(2-chloro-4-pyridyl)pyrazole 4-Bromo-1-(2-chloro-4-pyridyl)pyrazole 1342442-43-6 C8H5BrClN3
4-Bromo-1-(2-fluoro-4-pyridyl)pyrazole 4-Bromo-1-(2-fluoro-4-pyridyl)pyrazole 1353854-89-3 C8H5BrFN3
4-Bromo-1-(4-amino-2-pyridyl)pyrazole 4-Bromo-1-(4-amino-2-pyridyl)pyrazole 1251299-56-5 C8H7BrN4
4-Bromo-1-(oxan-4-yl)-1H-1,2,3-triazole 4-Bromo-1-(oxan-4-yl)-1H-1,2,3-triazole 1622844-04-5 C7H10BrN3O
4-bromo-2-(1H-imidazol-1-yl-d3)pyridine 4-bromo-2-(1H-imidazol-1-yl-d3)pyridine 2256707-30-7 C8H6BrN3
4-bromo-2-(1H-pyrazol-1-yl-d3)pyrimidine 4-bromo-2-(1H-pyrazol-1-yl-d3)pyrimidine 2256707-08-9 C7H5BrN4
4-Bromo-2-(2-methoxyphenyl)pyridine 4-Bromo-2-(2-methoxyphenyl)pyridine 876601-40-0 C12H10BrNO
4-Bromo-2-(2-trifluoromethylphenyl)pyridine 4-Bromo-2-(2-trifluoromethylphenyl)pyridine 1215071-44-5 C12H7BrF3N
4-Bromo-2-(3,5-difluorophenyl)pyridine 4-Bromo-2-(3,5-difluorophenyl)pyridine 1215073-95-2 C11H6BrF2N
4-Bromo-2-(3-hydroxypiperidin-1-yl)pyridine 4-Bromo-2-(3-hydroxypiperidin-1-yl)pyridine 1159816-77-9 C10H13BrN2O
4-Bromo-2-(4-aminophenyl)pyridine 4-Bromo-2-(4-aminophenyl)pyridine 1215072-10-8 C11H9BrN2
4-Bromo-2-(4-chlorophenyl)thiazole 4-Bromo-2-(4-chlorophenyl)thiazole 1353855-23-8 C9H5BrClNS
4-Bromo-2-(4-tert-butylphenyl)pyridine 4-Bromo-2-(4-tert-butylphenyl)pyridine 1563535-07-8 C15H16BrN
4-Bromo-2-(4-tolyl)thiazole 4-Bromo-2-(4-tolyl)thiazole 1142196-28-8 C10H8BrNS
4-Bromo-2-(N-methylpiperazin-1-yl)pyrimidine 4-Bromo-2-(N-methylpiperazin-1-yl)pyrimidine 1086381-75-0 C9H13BrN4
4-bromo-2-(tetrahydro-2H-pyran-2-yl)pyridine 4-bromo-2-(tetrahydro-2H-pyran-2-yl)pyridine 1622834-33-6 C10H12BrNO
4-Bromo-2-(thienyl)pyridine 4-Bromo-2-(thienyl)pyridine 1086381-45-4 C9H6BrNS
4-Bromo-2-cyclopentylpyridine 4-Bromo-2-cyclopentylpyridine 1086381-41-0 C10H12BrN
4-Bromo-3-(2-methyl-4-fluorophenyl)pyridine 4-Bromo-3-(2-methyl-4-fluorophenyl)pyridine 1374665-70-9 C12H9BrFN
4-Bromo-3-(2-tolyl)pyridine 4-Bromo-3-(2-tolyl)pyridine 1374664-48-8 C12H10BrN
4-Bromo-3-(4-chlorophenyl)pyridine 4-Bromo-3-(4-chlorophenyl)pyridine 1374664-65-9 C11H7BrClN
4-BROMO-3-(4-METHYLIMIDAZOL-1-YL)PYRIDINE 4-BROMO-3-(4-METHYLIMIDAZOL-1-YL)PYRIDINE 1563529-02-1 C9H8BrN3
4-Bromo-3-amino-6-(3-hydroxypiperidin-1-yl)pyridine 4-Bromo-3-amino-6-(3-hydroxypiperidin-1-yl)pyridine 1381935-50-7 C10H14BrN3O
4-Bromo-3-amino-6-(4-pyridyl)pyridine 4-Bromo-3-amino-6-(4-pyridyl)pyridine 1381934-54-8 C10H8BrN3
4-Bromo-3-amino-6-(cyclobutyl)pyridine 4-Bromo-3-amino-6-(cyclobutyl)pyridine 1381936-43-1 C9H11BrN2
4-Bromo-3-methyl-1-(cyclopropyl)-1H-pyrazole 4-Bromo-3-methyl-1-(cyclopropyl)-1H-pyrazole 1563530-25-5 C7H9BrN2
4-Bromo-5-(iso-propyl)-2-(diethylamino)thiazole 4-Bromo-5-(iso-propyl)-2-(diethylamino)thiazole 1643575-44-3 C10H17BrN2S
4-Bromo-5-methyl-1-cyclopropyl-1H-pyrazole 4-Bromo-5-methyl-1-cyclopropyl-1H-pyrazole 1513346-26-3 C7H9BrN2
4-Bromo-5-methyl-2-(cyclopropyl)pyridine 4-Bromo-5-methyl-2-(cyclopropyl)pyridine 1374665-66-3 C9H10BrN
4-Bromo-6-(3-methylpiperidin-1-yl)pyrimidine 4-Bromo-6-(3-methylpiperidin-1-yl)pyrimidine 1314356-59-6 C10H14BrN3
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