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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
1-(iso-Propyl)-1H-pyrrol-3-amine 1-(iso-Propyl)-1H-pyrrol-3-amine 1622840-70-3 C7H12N2
1-[2-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDIN-4-YL]PIPERIDIN-2-ONE 1-[2-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDIN-4-YL]PIPERIDIN-2-ONE 1353053-06-1 C16H23BN2O3
1-Chloro-4-phenylpyrido[4,3-d]pyridazine 1-Chloro-4-phenylpyrido[4,3-d]pyridazine 863602-33-9 C13H8ClN3
2-(1-Acetoxy-1-methylethyl)pyrimidine-5-boronic acid pinacol ester 2-(1-Acetoxy-1-methylethyl)pyrimidine-5-boronic acid pinacol ester 1402174-52-0 C15H23BN2O4
2-(2-methoxyphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(2-methoxyphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223035-53-6 C18H22BNO3
2-(2-Methoxyphenyl)pyridine-3-boronic acid pinacol ester 2-(2-Methoxyphenyl)pyridine-3-boronic acid pinacol ester 2223053-69-6 C18H22BNO3
2-(2-Trifluoromethylphenyl)pyridine-3-boronic acid pinacol ester 2-(2-Trifluoromethylphenyl)pyridine-3-boronic acid pinacol ester 2223045-81-4 C18H19BF3NO2
2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)phenyl)pyridine 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)phenyl)pyridine 2223046-37-3 C18H19BF3NO2
2-(3,4-Difluorophenyl)pyridine-4-boronic acid 2-(3,4-Difluorophenyl)pyridine-4-boronic acid 2225173-47-5 C11H8BF2NO2
2-(3-Chlorophenyl)pyrimidine-5-boronic acid pinacol ester 2-(3-Chlorophenyl)pyrimidine-5-boronic acid pinacol ester 1402227-51-3 C16H18BClN2O2
2-(3-Furyl)pyridine-3-boronic acid pinacol ester 2-(3-Furyl)pyridine-3-boronic acid pinacol ester 2223044-46-8 C15H18BNO3
2-(3-Tolyl)pyridine-3-boronic acid 2-(3-Tolyl)pyridine-3-boronic acid 2225177-14-8 C12H12BNO2
2-(3-Trifluoromethylphenyl)pyridine-3-boronic acid pinacol ester 2-(3-Trifluoromethylphenyl)pyridine-3-boronic acid pinacol ester 2223051-64-5 C18H19BF3NO2
2-(4-Aminophenyl)pyridine-3-boronic acid pinacol ester 2-(4-Aminophenyl)pyridine-3-boronic acid pinacol ester 2223051-76-9 C17H21BN2O2
2-(4-cyclopropyl-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-(4-cyclopropyl-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2223040-46-6 C16H23BO2
2-(4-Fluorophenyl)pyridine-3-boronic acid 2-(4-Fluorophenyl)pyridine-3-boronic acid 2225173-24-8 C11H9BFNO2
2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)thiazole 2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)thiazole 2223035-84-3 C13H16BN3O2S
2-(5-(sec-butyl)furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-(5-(sec-butyl)furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2222995-96-0 C14H23BO3
2-(Cyclobutyl)-6-(oxolan-3-yl)pyridine-4-boronic acid pinacol ester 2-(Cyclobutyl)-6-(oxolan-3-yl)pyridine-4-boronic acid pinacol ester 2223009-10-5 C19H28BNO3
2-(Diethylamino)pyridine-4-boronic acid 2-(Diethylamino)pyridine-4-boronic acid 2225155-86-0 C9H15BN2O2
2-(ethoxy-d5)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(ethoxy-d5)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241875-56-7 C13H20BNO3
2-(Imidazol-1-yl)pyridine-4-boronic acid 2-(Imidazol-1-yl)pyridine-4-boronic acid 1644060-49-0 C8H8BN3O2
2-(iso-Propyl)-5-(methoxycarbonyl)pyridine-3-boronic acid pinacol ester 2-(iso-Propyl)-5-(methoxycarbonyl)pyridine-3-boronic acid pinacol ester 2223034-80-6 C16H24BNO4
2-(iso-Propyl)-5-trifluoromethylpyridine-3-boronic acid pinacol ester 2-(iso-Propyl)-5-trifluoromethylpyridine-3-boronic acid pinacol ester 2223048-47-1 C15H21BF3NO2
2-(n-Propyl)-6-cyanopyridine-4-boronic acid pinacol ester 2-(n-Propyl)-6-cyanopyridine-4-boronic acid pinacol ester 2223046-80-6 C15H21BN2O2
2-(Oxan-2-yl)-6-(1,4-dioxan-2-yl)pyridine-4-boronic acid pinacol ester 2-(Oxan-2-yl)-6-(1,4-dioxan-2-yl)pyridine-4-boronic acid pinacol ester 2223002-85-3 C20H30BNO5
2-(phenyl-d5)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(phenyl-d5)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241867-12-7 C17H20BNO2
2-(propoxy-d7)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(propoxy-d7)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241867-21-8 C14H22BNO3
2-(propyl-d7)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(propyl-d7)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241867-22-9 C14H15BD7NO2
2-(pyridin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine 2-(pyridin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazine 2223051-30-5 C15H18BN3O2
2-(sec-butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-(sec-butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2222995-81-3 C13H22BNO2S
2-(tetrahydrofuran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridine 2-(tetrahydrofuran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridine 2222996-01-0 C16H21BF3NO3
2-(tetrahydrofuran-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridine 2-(tetrahydrofuran-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridine 2223003-39-0 C16H21BF3NO3
2,4-Dibromo-5-(3,4-difluorophenyl)pyridine 2,4-Dibromo-5-(3,4-difluorophenyl)pyridine 1381942-90-0 C11H5Br2F2N
2,4-Dibromo-5-(3-thienyl)pyridine 2,4-Dibromo-5-(3-thienyl)pyridine 1381935-43-8 C9H5Br2NS
2,4-Dibromo-6-(4-tetrahydropyranyl)pyridine 2,4-Dibromo-6-(4-tetrahydropyranyl)pyridine 1353853-76-5 C10H11Br2NO
2,4-Dichloro-6-(2-tolyl)pyrimidine 2,4-Dichloro-6-(2-tolyl)pyrimidine 1037500-30-3 C11H8Cl2N2
2,4-Dichloro-6-(3-pyridyl)pyrimidine 2,4-Dichloro-6-(3-pyridyl)pyrimidine 954232-60-1 C9H5Cl2N3
2,5-Dibromo-4-(1H-pyrrol-1-yl)pyridine 2,5-Dibromo-4-(1H-pyrrol-1-yl)pyridine 1381937-95-6 C9H6Br2N2
2,5-Dibromo-4-(3-methyl-1H-pyrazol-1-yl)pyridine 2,5-Dibromo-4-(3-methyl-1H-pyrazol-1-yl)pyridine 1381937-17-2 C9H7Br2N3
2,5-Dibromo-4-(cyclopropyl)pyridine 2,5-Dibromo-4-(cyclopropyl)pyridine 1381938-50-6 C8H7Br2N
2,6-bis(methyl-d3)pyridin-4-amine 2,6-bis(methyl-d3)pyridin-4-amine 1643543-54-7 C7H4D6N2
2,6-di(iso-propyl)pyrimidin-4-ol 2,6-di(iso-propyl)pyrimidin-4-ol 34127-02-1 C10H16N2O
2-AMINO-3-(CYCLOHEXYL)PYRIDINE 2-AMINO-3-(CYCLOHEXYL)PYRIDINE 1342418-34-1 C11H16N2
2-Amino-3-bromo-5-(2-tolyl)pyridine 2-Amino-3-bromo-5-(2-tolyl)pyridine 1381942-57-9 C12H11BrN2
2-Amino-3-bromo-5-(4-hydroxypiperidin-1-yl)pyridine 2-Amino-3-bromo-5-(4-hydroxypiperidin-1-yl)pyridine 1381937-84-3 C10H14BrN3O
2-amino-4-(1H-2-methylimidazol-1-yl)-6-cyclopropylpyrimidine 2-amino-4-(1H-2-methylimidazol-1-yl)-6-cyclopropylpyrimidine 1412955-09-9 C11H13N5
2-amino-4-(1H-4-methylimidazol-1-yl)-6-(tert-butyl)pyrimidine 2-amino-4-(1H-4-methylimidazol-1-yl)-6-(tert-butyl)pyrimidine 1412954-72-3 C12H17N5
2-amino-4-(1H-pyrrol-1-yl)-6-(tert-butyl)pyrimidine 2-amino-4-(1H-pyrrol-1-yl)-6-(tert-butyl)pyrimidine 1412959-66-0 C12H16N4
2-Amino-4-(2-methyl-1H-imidazol-1-yl)-6-methylpyrimidine 2-Amino-4-(2-methyl-1H-imidazol-1-yl)-6-methylpyrimidine 1412956-78-5 C9H11N5
2-Amino-4-(2-methylpiperidin-1-yl)-6-methylpyrimidine 2-Amino-4-(2-methylpiperidin-1-yl)-6-methylpyrimidine 1412958-65-6 C11H18N4
2-Amino-4-(3-furyl)-6-(iso-propyl)pyrimidine 2-Amino-4-(3-furyl)-6-(iso-propyl)pyrimidine 1412957-35-7 C11H13N3O
2-Amino-4-(4-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine 2-Amino-4-(4-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine 1412959-28-4 C9H11N5
2-amino-4-(4-methylpiperidin-1-yl)-6-cyclopropylpyrimidine 2-amino-4-(4-methylpiperidin-1-yl)-6-cyclopropylpyrimidine 1354754-72-5 C13H20N4
2-Amino-4-(imidazol-1-yl)pyrimidine 2-Amino-4-(imidazol-1-yl)pyrimidine 1314355-24-2 C7H7N5
2-amino-4-(iso-propyl)-6-(tert-butyl)pyrimidine 2-amino-4-(iso-propyl)-6-(tert-butyl)pyrimidine 1412960-94-1 C11H19N3
2-amino-4,6-dicyclopropylpyrimidine 2-amino-4,6-dicyclopropylpyrimidine 1343965-07-0 C10H13N3
2-Amino-4-bromo-5-(2-methoxyphenyl)pyridine 2-Amino-4-bromo-5-(2-methoxyphenyl)pyridine 1381933-28-3 C12H11BrN2O
2-Amino-4-bromo-5-(3-methoxyphenyl)pyridine 2-Amino-4-bromo-5-(3-methoxyphenyl)pyridine 1381942-85-3 C12H11BrN2O
2-Amino-4-bromo-5-ethylpyridine 2-Amino-4-bromo-5-ethylpyridine 1357580-41-6 C7H9BrN2
2-Amino-4-chloro-5-(2-pyridyl)pyridine 2-Amino-4-chloro-5-(2-pyridyl)pyridine 1381941-47-4 C10H8ClN3
2-Amino-4-chloro-5-(4-tolyl)pyridine 2-Amino-4-chloro-5-(4-tolyl)pyridine 1381941-15-6 C12H11ClN2
2-Amino-4-chloro-5-(cyclopentyl)pyridine 2-Amino-4-chloro-5-(cyclopentyl)pyridine 1381935-98-3 C10H13ClN2
2-Amino-4-morpholino-6-(iso-propyl)pyrimidine 2-Amino-4-morpholino-6-(iso-propyl)pyrimidine 1412958-20-3 C11H18N4O
2-Amino-5-bromo-4-(2-methylimidazol-1-yl)pyridine 2-Amino-5-bromo-4-(2-methylimidazol-1-yl)pyridine 1381937-67-2 C9H9BrN4
2-Amino-5-bromo-4-(3-fluorophenyl)pyridine 2-Amino-5-bromo-4-(3-fluorophenyl)pyridine 1381942-42-2 C11H8BrFN2
2-Amino-5-bromo-4-(cyclobutyl)pyridine 2-Amino-5-bromo-4-(cyclobutyl)pyridine 1381938-34-6 C9H11BrN2
2-Amino-5-bromo-4-(n-propyl)pyridine 2-Amino-5-bromo-4-(n-propyl)pyridine 1254043-53-2 C8H11BrN2
2-AMINO-6-(2-METHYLIMIDAZOL-1-YL)PYRIDINE 2-AMINO-6-(2-METHYLIMIDAZOL-1-YL)PYRIDINE 1314355-30-0 C9H10N4
2-AMINO-6-(3-METHYLPIPERIDIN-1-YL)PYRIDINE 2-AMINO-6-(3-METHYLPIPERIDIN-1-YL)PYRIDINE 1314355-23-1 C11H17N3
2-Bromo-3-(2-methyl-4-fluorophenyl)pyridine 2-Bromo-3-(2-methyl-4-fluorophenyl)pyridine 1417518-88-7 C12H9BrFN
2-Bromo-3-(2-tolyl)pyridine 2-Bromo-3-(2-tolyl)pyridine 1417518-15-0 C12H10BrN
2-Bromo-3-(3-trifluoromethylphenyl)pyridine 2-Bromo-3-(3-trifluoromethylphenyl)pyridine 1417518-73-0 C12H7BrF3N
2-Bromo-3-(4-trifluoromethylphenyl)thiophene 2-Bromo-3-(4-trifluoromethylphenyl)thiophene 459170-90-2 C11H6BrF3S
2-Bromo-3-(cyclobutyl)pyridine 2-Bromo-3-(cyclobutyl)pyridine 1417518-00-3 C9H10BrN
2-Bromo-3-(pyridin-2-yl)pyridine 2-Bromo-3-(pyridin-2-yl)pyridine 1356406-42-2 C10H7BrN2
2-Bromo-3-(sec-butyl)pyridine 2-Bromo-3-(sec-butyl)pyridine 1417519-69-7 C9H12BrN
2-Bromo-3-fluoro-4-ethylpyridine 2-Bromo-3-fluoro-4-ethylpyridine 1622843-65-5 C7H7BrFN
2-Bromo-3-methoxycarbonyl-4-cyclobutylpyridine 2-Bromo-3-methoxycarbonyl-4-cyclobutylpyridine 1622842-62-9 C11H12BrNO2
2-bromo-4-(1H-4-methylpyrozol-1-yl)-6-(tert-butyl)pyrimidine 2-bromo-4-(1H-4-methylpyrozol-1-yl)-6-(tert-butyl)pyrimidine 1412954-75-6 C12H15BrN4
2-Bromo-4-(1H-pyridin-2-one)-6-methylpyrimidine 2-Bromo-4-(1H-pyridin-2-one)-6-methylpyrimidine 1412960-69-0 C10H8BrN3O
2-bromo-4-(1H-pyrozol-1-yl)-6-cyclopropylpyrimidine 2-bromo-4-(1H-pyrozol-1-yl)-6-cyclopropylpyrimidine 1412958-88-3 C10H9BrN4
2-Bromo-4-(2-fluorophenyl)-6-methylpyrimidine 2-Bromo-4-(2-fluorophenyl)-6-methylpyrimidine 1412956-13-8 C11H8BrFN2
2-Bromo-4-(2-tolyl)-6-cyclopropylpyrimidine 2-Bromo-4-(2-tolyl)-6-cyclopropylpyrimidine 1412954-98-3 C14H13BrN2
2-Bromo-4-(2-trifluoromethylphenyl)-6-(iso-propyl)pyrimidine 2-Bromo-4-(2-trifluoromethylphenyl)-6-(iso-propyl)pyrimidine 1412953-29-7 C14H12BrF3N2
2-bromo-4-(3-furyl)-6-cyclopropylpyrimidine 2-bromo-4-(3-furyl)-6-cyclopropylpyrimidine 1412954-62-1 C11H9BrN2O
2-Bromo-4-(3-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine 2-Bromo-4-(3-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine 1412953-08-2 C9H9BrN4
2-Bromo-4-(3-pyridyl)-1,3,5-triazine 2-Bromo-4-(3-pyridyl)-1,3,5-triazine 1417518-97-8 C8H5BrN4
2-Bromo-4-(3-thienyl)-6-(iso-propyl)pyrimidine 2-Bromo-4-(3-thienyl)-6-(iso-propyl)pyrimidine 1412957-92-6 C11H11BrN2S
2-Bromo-4-(4-hydroxypiperidin-1-yl)pyrimidine 2-Bromo-4-(4-hydroxypiperidin-1-yl)pyrimidine 1314354-87-4 C9H12BrN3O
2-Bromo-4-(cyclohexyl)pyrimidine 2-Bromo-4-(cyclohexyl)pyrimidine 1131040-40-8 C10H13BrN2
2-bromo-4-(cyclopropyl)-6-(tert-butyl)pyrimidine 2-bromo-4-(cyclopropyl)-6-(tert-butyl)pyrimidine 1412955-53-3 C11H15BrN2
2-Bromo-4-(iso-propyl)pyrimidine-5-boronic acid 2-Bromo-4-(iso-propyl)pyrimidine-5-boronic acid 2225177-03-5 C7H10BBrN2O2
2-Bromo-4-(piperidin-1-yl)-6-methylpyrimidine 2-Bromo-4-(piperidin-1-yl)-6-methylpyrimidine 1412954-84-7 C10H14BrN3
2-bromo-4-(pyridin-4-yl)-6-cyclopropylpyrimidine 2-bromo-4-(pyridin-4-yl)-6-cyclopropylpyrimidine 1412961-13-7 C12H10BrN3
2-Bromo-4-(tert-butyl)-1,3,5-triazine 2-Bromo-4-(tert-butyl)-1,3,5-triazine 1417519-45-9 C7H10BrN3
2-Bromo-4-chloro-5-(2-thienyl)pyridine 2-Bromo-4-chloro-5-(2-thienyl)pyridine 1381940-70-0 C9H5BrClNS
2-Bromo-4-chloro-5-(n-propyl)pyridine 2-Bromo-4-chloro-5-(n-propyl)pyridine 1353856-98-0 C8H9BrClN
2-Bromo-4-methyl-1,3,5-triazine 2-Bromo-4-methyl-1,3,5-triazine 1417519-17-5 C4H4BrN3
2-Bromo-4-morpholino-6-(iso-propyl)pyrimidine 2-Bromo-4-morpholino-6-(iso-propyl)pyrimidine 1412953-83-3 C11H16BrN3O
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