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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-Amino-6-(2-tolyl)pyrimidine 2-Amino-6-(2-tolyl)pyrimidine 1159816-90-6 C11H11N3
2-Bromo-3-(2-pyridyl)furan 2-Bromo-3-(2-pyridyl)furan 1227960-18-0 C9H6BrNO
2-Bromo-3-(2-trifluoromethylphenyl)furan 2-Bromo-3-(2-trifluoromethylphenyl)furan 1227959-10-5 C11H6BrF3O
2-Bromo-3-(3-tolyl)pyridine 2-Bromo-3-(3-tolyl)pyridine 1417519-50-6 C12H10BrN
2-Bromo-3-(4-fluorophenyl)furan 2-Bromo-3-(4-fluorophenyl)furan 1227960-37-3 C10H6BrFO
2-Bromo-3-(5-pyrimidyl)thiophene 2-Bromo-3-(5-pyrimidyl)thiophene 71637-40-6 C8H5BrN2S
2-Bromo-3-(cyclohexyl)furan 2-Bromo-3-(cyclohexyl)furan 1227960-23-7 C10H13BrO
2-Bromo-3-(tert-butyl)pyridine 2-Bromo-3-(tert-butyl)pyridine 1211521-35-5 C9H12BrN
2-Bromo-3-fluoro-4-(3-furyl)pyridine 2-Bromo-3-fluoro-4-(3-furyl)pyridine 1622838-97-4 C9H5BrFNO
2-Bromo-3-phenylfuran 2-Bromo-3-phenylfuran 1381947-28-9 C10H7BrO
2-Bromo-4-(1H-imidazol-1-yl)-6-(iso-propyl)pyrimidine 2-Bromo-4-(1H-imidazol-1-yl)-6-(iso-propyl)pyrimidine 1412960-62-3 C10H11BrN4
2-bromo-4-(1H-pyrrol-1-yl)-6-(tert-butyl)pyrimidine 2-bromo-4-(1H-pyrrol-1-yl)-6-(tert-butyl)pyrimidine 1412957-10-8 C12H14BrN3
2-Bromo-4-(2-furyl)-1,3,5-triazine 2-Bromo-4-(2-furyl)-1,3,5-triazine 1417518-63-8 C7H4BrN3O
2-Bromo-4-(2-hydroxypiperidin-1-yl)pyrimidine 2-Bromo-4-(2-hydroxypiperidin-1-yl)pyrimidine 1314353-50-8 C9H12BrN3O
2-Bromo-4-(2-thienyl)-1,3,5-triazine 2-Bromo-4-(2-thienyl)-1,3,5-triazine 1417518-10-5 C7H4BrN3S
2-Bromo-4-(2-trifluoromethylphenyl)-6-cyclopropylpyrimidine 2-Bromo-4-(2-trifluoromethylphenyl)-6-cyclopropylpyrimidine 1412955-18-0 C14H10BrF3N2
2-Bromo-4-(3-hydroxypiperidin-1-yl)pyrimidine 2-Bromo-4-(3-hydroxypiperidin-1-yl)pyrimidine 1314355-02-6 C9H12BrN3O
2-Bromo-4-(3-tetrahydrofuranyl)pyrimidine 2-Bromo-4-(3-tetrahydrofuranyl)pyrimidine 1353853-64-1 C8H9BrN2O
2-bromo-4-(3-thienyl)-6-cyclopropylpyrimidine 2-bromo-4-(3-thienyl)-6-cyclopropylpyrimidine 1412961-49-9 C11H9BrN2S
2-Bromo-4-(4-methyl-1H-imidazol-1-yl)-6-methylpyrimidine 2-Bromo-4-(4-methyl-1H-imidazol-1-yl)-6-methylpyrimidine 1412960-40-7 C9H9BrN4
2-Bromo-4-(4-methyl-1H-pyrazol-1-yl)pyrimidine 2-Bromo-4-(4-methyl-1H-pyrazol-1-yl)pyrimidine 1314355-75-3 C8H7BrN4
2-bromo-4-(4-tetrahydropyranyl)-6-(tert-butyl)pyrimidine 2-bromo-4-(4-tetrahydropyranyl)-6-(tert-butyl)pyrimidine 1412956-37-6 C13H19BrN2O
2-bromo-4-(cyclopentyl)-6-(tert-butyl)pyrimidine 2-bromo-4-(cyclopentyl)-6-(tert-butyl)pyrimidine 1412960-61-2 C13H19BrN2
2-Bromo-4-(diethylamino)furan 2-Bromo-4-(diethylamino)furan 1622840-17-8 C8H12BrNO
2-Bromo-4-(iso-propyl)-1,3,5-triazine 2-Bromo-4-(iso-propyl)-1,3,5-triazine 1417519-43-7 C6H8BrN3
2-Bromo-4-(methylethylamino)thiophene 2-Bromo-4-(methylethylamino)thiophene 1622835-60-2 C7H10BrNS
2-Bromo-4-(piperidin-1-yl)-6-(iso-propyl)pyrimidine 2-Bromo-4-(piperidin-1-yl)-6-(iso-propyl)pyrimidine 1412956-21-8 C12H18BrN3
2-Bromo-4-(pyrimidin-5-yl)-6-(iso-propyl)pyrimidine 2-Bromo-4-(pyrimidin-5-yl)-6-(iso-propyl)pyrimidine 1412959-55-7 C11H11BrN4
2-bromo-4-(pyrrolidin-1-yl)-6-(tert-butyl)pyrimidine 2-bromo-4-(pyrrolidin-1-yl)-6-(tert-butyl)pyrimidine 1412959-59-1 C12H18BrN3
2-Bromo-4-chloro-5-(3-thienyl)pyridine 2-Bromo-4-chloro-5-(3-thienyl)pyridine 1381937-52-5 C9H5BrClNS
2-Bromo-4-chloro-5-(4-pyridyl)pyridine 2-Bromo-4-chloro-5-(4-pyridyl)pyridine 1381937-56-9 C10H6BrClN2
2-Bromo-4-cyclohexyl-6-(iso-propyl)pyrimidine 2-Bromo-4-cyclohexyl-6-(iso-propyl)pyrimidine 1622839-76-2 C13H19BrN2
2-Bromo-4-ethyl-1,3,5-triazine 2-Bromo-4-ethyl-1,3,5-triazine 1417519-18-6 C5H6BrN3
2-bromo-4-morpholino-6-cyclopropylpyrimidine 2-bromo-4-morpholino-6-cyclopropylpyrimidine 1412957-28-8 C11H14BrN3O
2-Bromo-5-(3-furyl)furan 2-Bromo-5-(3-furyl)furan 1412956-60-5 C8H5BrO2
2-Bromo-5-(4-fluorophenyl)furan 2-Bromo-5-(4-fluorophenyl)furan 1026858-94-5 C10H6BrFO
2-Bromo-5-(5-pyrimidyl)furan 2-Bromo-5-(5-pyrimidyl)furan 1412955-66-8 C8H5BrN2O
2-Bromo-5-(cyclohexyl)furan 2-Bromo-5-(cyclohexyl)furan 1412958-55-4 C10H13BrO
2-Bromo-5-(morpholino)furan 2-Bromo-5-(morpholino)furan 1622843-22-4 C8H10BrNO2
2-Bromo-5-cyclopentylpyridine-4-boronic acid pinacol ester 2-Bromo-5-cyclopentylpyridine-4-boronic acid pinacol ester 1402234-01-8 C16H23BBrNO2
2-Bromo-5-methyl-4-cyclopropylpyridine 2-Bromo-5-methyl-4-cyclopropylpyridine 1381938-07-3 C9H10BrN
2-Bromo-6-(2-pyridyl)pyridine-4-boronic acid pinacol ester 2-Bromo-6-(2-pyridyl)pyridine-4-boronic acid pinacol ester 2223034-97-5 C16H18BBrN2O2
2-Bromo-6-(3-furyl)pyridine-4-boronic acid 2-Bromo-6-(3-furyl)pyridine-4-boronic acid 2225174-03-6 C9H7BBrNO3
2-Bromo-6-(acetyl) 
pyridine-4-boronic acid pinacol ester 2-Bromo-6-(acetyl) pyridine-4-boronic acid pinacol ester 2223051-91-8 C13H17BBrNO3
2-Bromo-6-(cyclopentyl)pyridine-4-boronic acid 2-Bromo-6-(cyclopentyl)pyridine-4-boronic acid 2225180-33-4 C10H13BBrNO2
2-Bromo-6-(Oxolan-2-yl)pyridine-4-boronic acid pinacol ester 2-Bromo-6-(Oxolan-2-yl)pyridine-4-boronic acid pinacol ester 2223003-38-9 C15H21BBrNO3
2-Bromo-6-(thiazol-5-yl)pyridine-4-boronic acid 2-Bromo-6-(thiazol-5-yl)pyridine-4-boronic acid 2225170-60-3 C8H6BBrN2O2S
2-Bromo-6-chloropyridine-4-boronic acid 2-Bromo-6-chloropyridine-4-boronic acid 2225154-90-3 C5H4BBrClNO2
2-Chloro-3-(2-chloropyrimidin-4-yl)pyridine 2-Chloro-3-(2-chloropyrimidin-4-yl)pyridine 870221-39-9 C9H5Cl2N3
2-Chloro-3-(3-tolyl)pyridine 2-Chloro-3-(3-tolyl)pyridine 1226409-19-3 C12H10ClN
2-Chloro-3-(4-tolyl)pyridine 2-Chloro-3-(4-tolyl)pyridine 1225883-99-7 C12H10ClN
2-Chloro-3-(thiazol-4-yl)pyridine 2-Chloro-3-(thiazol-4-yl)pyridine 1417519-54-0 C8H5ClN2S
2-chloro-4-(1,4-dioxan-2-yl)pyrimidine 2-chloro-4-(1,4-dioxan-2-yl)pyrimidine 2222935-34-2 C8H9ClN2O2
2-chloro-4-(1H-imidazol-1-yl)-6-cyclopropylpyrimidine 2-chloro-4-(1H-imidazol-1-yl)-6-cyclopropylpyrimidine 1412953-71-9 C10H9ClN4
2-Chloro-4-(1H-pyridin-2-one)-6-(iso-propyl)pyrimidine 2-Chloro-4-(1H-pyridin-2-one)-6-(iso-propyl)pyrimidine 1412955-27-1 C12H12ClN3O
2-Chloro-4-(2-fluorophenyl)-6-(iso-propyl)pyrimidine 2-Chloro-4-(2-fluorophenyl)-6-(iso-propyl)pyrimidine 1412959-74-0 C13H12ClFN2
2-Chloro-4-(2-methylpiperidin-1-yl)-6-methylpyrimidine 2-Chloro-4-(2-methylpiperidin-1-yl)-6-methylpyrimidine 1248236-09-0 C11H16ClN3
2-chloro-4-(2-trifluoromethylphenyl)-6-(tert-butyl)pyrimidine 2-chloro-4-(2-trifluoromethylphenyl)-6-(tert-butyl)pyrimidine 1412955-29-3 C15H14ClF3N2
2-CHLORO-4-(3-METHYL-1H-PYRAZOL-1-YL)PYRIMIDINE 2-CHLORO-4-(3-METHYL-1H-PYRAZOL-1-YL)PYRIMIDINE 1233932-35-8 C8H7ClN4
2-Chloro-4-(3-methylpiperidin-1-yl)-6-methylpyrimidine 2-Chloro-4-(3-methylpiperidin-1-yl)-6-methylpyrimidine 1248198-48-2 C11H16ClN3
2-Chloro-4-(4-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine 2-Chloro-4-(4-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine 1248047-69-9 C9H9ClN4
2-Chloro-4-(4-tert-butylphenyl)pyrimidine 2-Chloro-4-(4-tert-butylphenyl)pyrimidine 954236-01-2 C14H15ClN2
2-Chloro-4-(4-tolyl)-1,3,5-triazine 2-Chloro-4-(4-tolyl)-1,3,5-triazine 1417518-77-4 C10H8ClN3
2-chloro-4-(iso-propyl)-6-(tert-butyl)pyrimidine 2-chloro-4-(iso-propyl)-6-(tert-butyl)pyrimidine 1412959-62-6 C11H17ClN2
2-chloro-4-(piperidin-1-yl)-6-cyclopropylpyrimidine 2-chloro-4-(piperidin-1-yl)-6-cyclopropylpyrimidine 1412961-34-2 C12H16ClN3
2-chloro-4-(pyridin-2-yl)-6-(tert-butyl)pyrimidine 2-chloro-4-(pyridin-2-yl)-6-(tert-butyl)pyrimidine 1412961-63-7 C13H14ClN3
2-chloro-6-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-chloro-6-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223008-78-2 C16H23BClNO3
2-chloro-6-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-chloro-6-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223036-03-9 C14H21BClNO2
2-Cyano-6-(N-Boc-morpholin-2-yl)pyridine-4-boronic acid pinacol ester 2-Cyano-6-(N-Boc-morpholin-2-yl)pyridine-4-boronic acid pinacol ester 2223003-74-3 C21H30BN3O5
2-cyclobutoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-cyclobutoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 1352037-27-4 C13H20BNO3S
2-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridine 2-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridine 2223036-09-5 C18H25BF3NO2
2-Cyclohexyl-6-(piperidin-3-yl)pyridine-4-boronic acid 2-Cyclohexyl-6-(piperidin-3-yl)pyridine-4-boronic acid 2225152-61-2 C16H25BN2O2
2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine 2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine 2223049-58-7 C14H21BN2O2
2-cyclopropyl-6-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-cyclopropyl-6-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223036-45-9 C19H28BNO3
2-cyclopropyl-6-cyclopentyl-4-hydroxypyrimidine 2-cyclopropyl-6-cyclopentyl-4-hydroxypyrimidine 1412958-13-4 C12H16N2O
2-Ethyl-5-(methoxycarbonyl)pyridine-3-boronic acid 2-Ethyl-5-(methoxycarbonyl)pyridine-3-boronic acid 2225170-95-4 C9H12BNO4
2-Ethyl-5-cyanopyridine-3-boronic acid pinacol ester 2-Ethyl-5-cyanopyridine-3-boronic acid pinacol ester 2223042-50-8 C14H19BN2O2
2-Fluoro-3-bromo-4-(2-thienyl)pyridine 2-Fluoro-3-bromo-4-(2-thienyl)pyridine 1622843-67-7 C9H5BrFNS
2-Fluoro-3-bromo-4-(iso-butyl)pyridine 2-Fluoro-3-bromo-4-(iso-butyl)pyridine 1622838-90-7 C9H11BrFN
2-Fluoro-5-(methoxycarbonyl)pyridine-3-boronic acid 2-Fluoro-5-(methoxycarbonyl)pyridine-3-boronic acid 2225175-76-6 C7H7BFNO4
2-Fluoro-6-(2-fluorophenyl)pyridine 2-Fluoro-6-(2-fluorophenyl)pyridine 511522-78-4 C11H7F2N
2-Fluoro-6-(2-furyl)pyridine-3-boronic acid pinacol ester 2-Fluoro-6-(2-furyl)pyridine-3-boronic acid pinacol ester 2223034-98-6 C15H17BFNO3
2-Fluoro-6-(3-thienyl)pyridine-3-boronic acid 2-Fluoro-6-(3-thienyl)pyridine-3-boronic acid 2225177-72-8 C9H7BFNO2S
2-Fluoro-6-(4-chlorophenyl)pyridine 2-Fluoro-6-(4-chlorophenyl)pyridine 1563529-46-3 C11H7ClFN
2-Fluoro-6-(cyclopropyl)pyridine-4-boronic acid 2-Fluoro-6-(cyclopropyl)pyridine-4-boronic acid 2225176-17-8 C8H9BFNO2
2-Fluoro-6-(pyrimidin-2-yl)pyridine 2-Fluoro-6-(pyrimidin-2-yl)pyridine 1563528-99-3 C9H6FN3
2-Fluoro-6-(sec-butyl)pyridine 2-Fluoro-6-(sec-butyl)pyridine 1563530-05-1 C9H12FN
2-Fluoro-6-(thiazol-4-yl)pyridine-3-boronic acid pinacol ester 2-Fluoro-6-(thiazol-4-yl)pyridine-3-boronic acid pinacol ester 2223053-09-4 C14H16BFN2O2S
2-Fluoro-6-iodopyridine-4-boronic acid pinacol ester 2-Fluoro-6-iodopyridine-4-boronic acid pinacol ester 2223048-53-9 C11H14BFINO2
2-Hydroxy-3-(3-furyl)pyridine 2-Hydroxy-3-(3-furyl)pyridine 1026359-52-3 C9H7NO2
2-Hydroxy-3-(4-methoxyphenyl)pyridine 2-Hydroxy-3-(4-methoxyphenyl)pyridine 143074-71-9 C12H11NO2
2-hydroxy-4-(1H-2-methylimidazol-1-yl)-6-cyclopropylpyrimidine 2-hydroxy-4-(1H-2-methylimidazol-1-yl)-6-cyclopropylpyrimidine 1412957-59-5 C11H12N4O
2-hydroxy-4-(1H-4-methylimidazol-1-yl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(1H-4-methylimidazol-1-yl)-6-(tert-butyl)pyrimidine 1412961-06-8 C12H16N4O
2-hydroxy-4-(1H-pyrozol-1-yl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(1H-pyrozol-1-yl)-6-(tert-butyl)pyrimidine 1412955-86-2 C11H14N4O
2-Hydroxy-4-(1H-pyrrol-1-yl)-6-methylpyrimidine 2-Hydroxy-4-(1H-pyrrol-1-yl)-6-methylpyrimidine 1412958-71-4 C9H9N3O
2-Hydroxy-4-(2-methyl-1H-imidazol-1-yl)-6-methylpyrimidine 2-Hydroxy-4-(2-methyl-1H-imidazol-1-yl)-6-methylpyrimidine 1412960-98-5 C9H10N4O
2-Hydroxy-4-(2-thienyl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(2-thienyl)-6-(iso-propyl)pyrimidine 1412955-04-4 C11H12N2OS
2-hydroxy-4-(4-chlorophenyl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(4-chlorophenyl)-6-(tert-butyl)pyrimidine 1412953-06-0 C14H15ClN2O
2-Hydroxy-4-(4-methyl-1H-imidazol-1-yl)-6-methylpyrimidine 2-Hydroxy-4-(4-methyl-1H-imidazol-1-yl)-6-methylpyrimidine 1412953-03-7 C9H10N4O
2-hydroxy-4-(cyclopentyl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(cyclopentyl)-6-(tert-butyl)pyrimidine 1412957-85-7 C13H20N2O
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