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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
4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidine 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidine 2223029-42-1 C15H18BN3O2
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(thiophen-3-yl)thiazole 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(thiophen-3-yl)thiazole 1402166-56-6 C13H16BNO2S2
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5'-bithiazole 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5'-bithiazole 2223037-75-8 C12H15BN2O2S2
4-(Cyclobutyl)-1,3,5-triazin-2-amine 4-(Cyclobutyl)-1,3,5-triazin-2-amine 1417519-59-5 C7H10N4
4-(Cyclopentyl)pyridine-3-boronic acid 4-(Cyclopentyl)pyridine-3-boronic acid 2225180-18-5 C10H14BNO2
4-(Cyclopropyl)-1,3,5-triazin-2-amine 4-(Cyclopropyl)-1,3,5-triazin-2-amine 1411563-37-5 C6H8N4
4-(n-Propyl)pyridine-3-boronic acid 4-(n-Propyl)pyridine-3-boronic acid 553652-71-4 C8H12BNO2
4-(Piperidino)furan-2-boronic acid 4-(Piperidino)furan-2-boronic acid 2225170-09-0 C9H14BNO3
4-(prop-1-en-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(prop-1-en-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223011-70-7 C14H20BNO2
4-(Pyrimidin-5-yl)furan-2-boronic acid pinacol ester 4-(Pyrimidin-5-yl)furan-2-boronic acid pinacol ester 2223049-66-7 C14H17BN2O3
4-(tetrahydrofuran-3-yl)pyrimidin-2-ol 4-(tetrahydrofuran-3-yl)pyrimidin-2-ol 1866942-27-9 C8H10N2O2
4,4,5,5-tetramethyl-2-(3-(tetrahydrofuran-2-yl)phenyl)-1,3,2-dioxaborolane 4,4,5,5-tetramethyl-2-(3-(tetrahydrofuran-2-yl)phenyl)-1,3,2-dioxaborolane 2223006-66-2 C16H23BO3
4,5-Dibromo-2-(tert-butoxy)pyridine 4,5-Dibromo-2-(tert-butoxy)pyridine 1381941-61-2 C9H11Br2NO
4,6-Dichloro-2-(2-fluorophenyl)pyrimidine 4,6-Dichloro-2-(2-fluorophenyl)pyrimidine 1188236-93-2 C10H5Cl2FN2
4-Amino-2-(2-methyl-4-fluorophenyl)pyrimidine 4-Amino-2-(2-methyl-4-fluorophenyl)pyrimidine 1215074-02-4 C11H10FN3
4-Amino-2-(4-methoxyphenyl)pyrimidine 4-Amino-2-(4-methoxyphenyl)pyrimidine 90832-58-9 C11H11N3O
4-Amino-2-(cyclobutoxy)thiazole 4-Amino-2-(cyclobutoxy)thiazole 1314353-41-7 C7H10N2OS
4-Amino-2-(iso-propyl)-6-(1H-imidazol-1-yl)pyrimidine 4-Amino-2-(iso-propyl)-6-(1H-imidazol-1-yl)pyrimidine 1412952-97-6 C10H13N5
4-Amino-2-(iso-propyl)-6-(2-methylpiperidin-1-yl)-pyrimidine 4-Amino-2-(iso-propyl)-6-(2-methylpiperidin-1-yl)-pyrimidine 1412960-71-4 C13H22N4
4-Amino-2-(pyridin-2-yl)pyrimidine-5-boronic acid pinacol ester 4-Amino-2-(pyridin-2-yl)pyrimidine-5-boronic acid pinacol ester 2223054-09-7 C15H19BN4O2
4-Amino-2-cyclopropyl-6-(3-methyl-1H-pyrazol-1-yl)pyrimidine 4-Amino-2-cyclopropyl-6-(3-methyl-1H-pyrazol-1-yl)pyrimidine 1412958-54-3 C11H13N5
4-Amino-2-cyclopropyl-6-(4-methylimidazol-1-yl)pyrimidine 4-Amino-2-cyclopropyl-6-(4-methylimidazol-1-yl)pyrimidine 1412954-22-3 C11H13N5
4-Amino-2-methyl-6-(iso-propoxy)pyrimidine 4-Amino-2-methyl-6-(iso-propoxy)pyrimidine 139654-17-4 C8H13N3O
4-Amino-6-(2-chlorophenyl)-2-(iso-propyl)pyrimidine 4-Amino-6-(2-chlorophenyl)-2-(iso-propyl)pyrimidine 1304559-80-5 C13H14ClN3
4-amino-6-cyclobutyl-2-methylpyrimidine 4-amino-6-cyclobutyl-2-methylpyrimidine 1412954-95-0 C9H13N3
4-Bromo-2-(4-trifluoromethylphenyl)pyrimidine 4-Bromo-2-(4-trifluoromethylphenyl)pyrimidine 1215071-91-2 C11H6BrF3N2
4-Bromo-2-(cyclopentyl)pyrimidine 4-Bromo-2-(cyclopentyl)pyrimidine 1086381-87-4 C9H11BrN2
4-Bromo-2-(iso-propyl)-6-(2-methylpiperidin-1-yl)-pyrimidine 4-Bromo-2-(iso-propyl)-6-(2-methylpiperidin-1-yl)-pyrimidine 1412953-80-0 C13H20BrN3
4-Bromo-2-(iso-propyl)-6-(3-methylpiperidin-1-yl)pyrimidine 4-Bromo-2-(iso-propyl)-6-(3-methylpiperidin-1-yl)pyrimidine 1412953-94-6 C13H20BrN3
4-Bromo-2-(oxan-4-yl)-5-fluoropyridine 4-Bromo-2-(oxan-4-yl)-5-fluoropyridine 1643576-19-5 C10H11BrFNO
4-Bromo-2-amino-5-(2-furyl)pyridine 4-Bromo-2-amino-5-(2-furyl)pyridine 1381933-36-3 C9H7BrN2O
4-Bromo-2-amino-5-(3-thienyl)pyridine 4-Bromo-2-amino-5-(3-thienyl)pyridine 1381933-85-2 C9H7BrN2S
4-Bromo-2-cyclopropyl-6-(2-chlorophenyl)pyrimidine 4-Bromo-2-cyclopropyl-6-(2-chlorophenyl)pyrimidine 1412957-24-4 C13H10BrClN2
4-Bromo-2-cyclopropyl-6-(2-pyridyl)pyrimidine 4-Bromo-2-cyclopropyl-6-(2-pyridyl)pyrimidine 1412958-23-6 C12H10BrN3
4-Bromo-2-cyclopropyl-6-(4-tetrahydropyranyl)pyrimidine 4-Bromo-2-cyclopropyl-6-(4-tetrahydropyranyl)pyrimidine 1412957-14-2 C12H15BrN2O
4-Bromo-2-cyclopropyl-6-(morpholino)pyrimidine 4-Bromo-2-cyclopropyl-6-(morpholino)pyrimidine 1412959-37-5 C11H14BrN3O
4-bromo-2-methyl-6-(1H-2-methylimidazol-1-yl)pyrimidine 4-bromo-2-methyl-6-(1H-2-methylimidazol-1-yl)pyrimidine 1412961-90-0 C9H9BrN4
4-Bromo-2-methyl-6-(n-propyl)pyrimidine 4-Bromo-2-methyl-6-(n-propyl)pyrimidine 1412959-64-8 C8H11BrN2
4-bromo-2-methyl-6-(pyridin-2-yl)pyrimidine 4-bromo-2-methyl-6-(pyridin-2-yl)pyrimidine 1412961-78-4 C10H8BrN3
4-Bromo-3-(n-propyl)pyridine 4-Bromo-3-(n-propyl)pyridine 1314356-43-8 C8H10BrN
4-Bromo-3-fluoro-2-(iso-butyl)pyridine 4-Bromo-3-fluoro-2-(iso-butyl)pyridine 1643537-86-3 C9H11BrFN
4-Bromo-3-fluoro-6-(oxan-4-yl)pyridine 4-Bromo-3-fluoro-6-(oxan-4-yl)pyridine 1643576-44-6 C10H11BrFNO
4-Bromo-5-(2-pyridyl)thiazole 4-Bromo-5-(2-pyridyl)thiazole 1417519-34-6 C8H5BrN2S
4-Bromo-6-(1-methylethyl)-2-pyridinecarbonitrile 4-Bromo-6-(1-methylethyl)-2-pyridinecarbonitrile 1242968-50-8 C9H9BrN2
4-bromo-6-(2-furyl)-2-methylpyrimidine 4-bromo-6-(2-furyl)-2-methylpyrimidine 1412960-04-3 C9H7BrN2O
4-bromo-6-cyclohexyl-2-methylpyrimidine 4-bromo-6-cyclohexyl-2-methylpyrimidine 1412959-73-9 C11H15BrN2
4-chloro-2-(iso-propyl)-6-(1H-pyrrol-1-yl)pyrimidine 4-chloro-2-(iso-propyl)-6-(1H-pyrrol-1-yl)pyrimidine 1412956-83-2 C11H12ClN3
4-chloro-2-(iso-propyl)-6-(2-trifluoromethylphenyl)-pyrimidine 4-chloro-2-(iso-propyl)-6-(2-trifluoromethylphenyl)-pyrimidine 1412956-45-6 C14H12ClF3N2
4-chloro-2-(iso-propyl)-6-phenylpyrimidine 4-chloro-2-(iso-propyl)-6-phenylpyrimidine 65010-24-4 C13H13ClN2
4-Chloro-2-cyclopropyl-6-(4-methyl-1H-pyrazol-1-yl)pyrimidine 4-Chloro-2-cyclopropyl-6-(4-methyl-1H-pyrazol-1-yl)pyrimidine 1412958-57-6 C11H11ClN4
4-Chloro-5-(cyclobutyl)pyridine-2-boronic acid pinacol ester 4-Chloro-5-(cyclobutyl)pyridine-2-boronic acid pinacol ester 2223049-49-6 C15H21BClNO2
4-chloro-5-cyclopropyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-chloro-5-cyclopropyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223053-50-5 C14H19BClNO2
4-chloro-6-(2-fluorophenyl)-2-(iso-propyl)pyrimidine 4-chloro-6-(2-fluorophenyl)-2-(iso-propyl)pyrimidine 1412957-98-2 C13H12ClFN2
4-chloro-6-(4-chlorophenyl)-2-methylpyrimidine 4-chloro-6-(4-chlorophenyl)-2-methylpyrimidine 1354748-50-7 C11H8Cl2N2
4-chloro-6-cyclopropyl-2-(propan-2-yl)pyrimidine 4-chloro-6-cyclopropyl-2-(propan-2-yl)pyrimidine 1283322-98-4 C10H13ClN2
4-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 4-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2223046-56-6 C12H18BNO2S
4-Ethyl-1,3,5-triazin-2-amine 4-Ethyl-1,3,5-triazin-2-amine 30360-34-0 C5H8N4
4-Fluoro-2-(1H-pyrazol-1-yl)pyridine-5-boronic acid 4-Fluoro-2-(1H-pyrazol-1-yl)pyridine-5-boronic acid 2225176-35-0 C8H7BFN3O2
4-Fluoro-2-(2-aminophenyl)pyridine 4-Fluoro-2-(2-aminophenyl)pyridine 1563530-76-6 C11H9FN2
4-Fluoro-2-(3-bromophenyl)pyridine 4-Fluoro-2-(3-bromophenyl)pyridine 1563529-99-6 C11H7BrFN
4-Fluoro-2-(3-methoxyphenyl)pyridine 4-Fluoro-2-(3-methoxyphenyl)pyridine 1497434-84-0 C12H10FNO
4-Fluoro-2-(4-methyl-1H-pyrazol-1-yl)pyridine-5-boronic acid pinacol ester 4-Fluoro-2-(4-methyl-1H-pyrazol-1-yl)pyridine-5-boronic acid pinacol ester 2223033-93-8 C15H19BFN3O2
4-Fluoro-2-(4-tolyl)pyridine 4-Fluoro-2-(4-tolyl)pyridine 1563529-60-1 C12H10FN
4-Fluoro-2-(diethylamino)pyridine-5-boronic acid 4-Fluoro-2-(diethylamino)pyridine-5-boronic acid 2225175-61-9 C9H14BFN2O2
4-Fluoro-2-(n-propyl)pyridine 4-Fluoro-2-(n-propyl)pyridine 1563531-51-0 C8H10FN
4-Fluoro-2-(piperidin-1-yl)pyridine-5-boronic acid 4-Fluoro-2-(piperidin-1-yl)pyridine-5-boronic acid 2225174-76-3 C10H14BFN2O2
4-Fluoro-2-(tert-butoxy)pyridine-5-boronic acid pinacol ester 4-Fluoro-2-(tert-butoxy)pyridine-5-boronic acid pinacol ester 2223045-25-6 C15H23BFNO3
4-Fluoro-2-(thiazol-2-yl)pyridine-5-boronic acid 4-Fluoro-2-(thiazol-2-yl)pyridine-5-boronic acid 2225175-79-9 C8H6BFN2O2S
4-Fluoro-3-bromopyridine-5-boronic acid 4-Fluoro-3-bromopyridine-5-boronic acid 2225177-26-2 C5H4BBrFNO2
4-Hydroxy-2-(cyclobutyl)pyrimidine 4-Hydroxy-2-(cyclobutyl)pyrimidine 1159816-67-7 C8H10N2O
4-Hydroxy-2-(iso-propyl)-6-(1H-4-methylimidazol-1-yl)-pyrimidine 4-Hydroxy-2-(iso-propyl)-6-(1H-4-methylimidazol-1-yl)-pyrimidine 1412956-89-8 C11H14N4O
4-Hydroxy-2-(iso-propyl)-6-(4-tetrahydropyranyl)pyrimidine 4-Hydroxy-2-(iso-propyl)-6-(4-tetrahydropyranyl)pyrimidine 1412958-05-4 C12H18N2O2
4-Hydroxy-2-(iso-propyl)-6-(tert-butoxy)pyrimidine 4-Hydroxy-2-(iso-propyl)-6-(tert-butoxy)pyrimidine 1412958-06-5 C11H18N2O2
4-Hydroxy-2-cyclopropyl-6-(3-thienyl)pyrimidine 4-Hydroxy-2-cyclopropyl-6-(3-thienyl)pyrimidine 1412953-07-1 C11H10N2OS
4-Hydroxy-2-cyclopropyl-6-(imidazol-1-yl)pyrimidine 4-Hydroxy-2-cyclopropyl-6-(imidazol-1-yl)pyrimidine 1412956-09-2 C10H10N4O
4-hydroxy-2-methyl-6-(2-methylpiperidin-1-yl)pyrimidine 4-hydroxy-2-methyl-6-(2-methylpiperidin-1-yl)pyrimidine 1412955-39-5 C11H17N3O
4-Hydroxy-2-methyl-6-(iso-propoxy)pyrimidine 4-Hydroxy-2-methyl-6-(iso-propoxy)pyrimidine 38249-36-4 C8H12N2O2
5-(1H-Pyridin-2-one)pyridine-3-boronic acid pinacol ester 5-(1H-Pyridin-2-one)pyridine-3-boronic acid pinacol ester 1402172-63-7 C16H19BN2O3
5-(2-Methoxyphenyl)pyridine-2-boronic acid pinacol ester 5-(2-Methoxyphenyl)pyridine-2-boronic acid pinacol ester 1402226-80-5 C18H22BNO3
5-(2-Methyl-4-fluorophenyl)pyridine-3-boronic acid 5-(2-Methyl-4-fluorophenyl)pyridine-3-boronic acid 2225172-96-1 C12H11BFNO2
5-(2-TETRAHYDROFURANYL)PYRIDINE-3-BORONIC ACID 5-(2-TETRAHYDROFURANYL)PYRIDINE-3-BORONIC ACID 2225153-28-4 C9H12BNO3
5-(3, 5-Difluorophenyl)pyridine-3-boronic acid pinacol ester 5-(3, 5-Difluorophenyl)pyridine-3-boronic acid pinacol ester 1402227-57-9 C17H18BF2NO2
5-(3-Chlorophenyl)pyridine-3-boronic acid pinacol ester 5-(3-Chlorophenyl)pyridine-3-boronic acid pinacol ester 1402227-41-1 C17H19BClNO2
5-(3-Fluorophenyl)pyridine-3-boronic acid 5-(3-Fluorophenyl)pyridine-3-boronic acid 1293389-53-3 C11H9BFNO2
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(3-(trifluoromethyl)phenyl)thiazole 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(3-(trifluoromethyl)phenyl)thiazole 1402237-80-2 C16H17BF3NO2S
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2-d 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2-d 2241867-62-7 C10H14BDN2O2
5-(4-Bromopyridin-2-yl)furan-2-boronic acid 5-(4-Bromopyridin-2-yl)furan-2-boronic acid 2225176-10-1 C9H7BBrNO3
5-(4-Methylimidazol-1-yl)pyridine-3-boronic acid 5-(4-Methylimidazol-1-yl)pyridine-3-boronic acid 2225173-95-3 C9H10BN3O2
5-(4-Tolyl)pyridine-2-boronic acid pinacol ester 5-(4-Tolyl)pyridine-2-boronic acid pinacol ester 1402166-78-2 C18H22BNO2
5-(4-Trfluoromethylphenyl)pyridine-2-boronic acid pinacol ester 5-(4-Trfluoromethylphenyl)pyridine-2-boronic acid pinacol ester 1402233-65-1 C18H19BF3NO2
5-(5-pyrimidyl)pyridine-3-boronic acid pinacol ester 5-(5-pyrimidyl)pyridine-3-boronic acid pinacol ester 2223051-18-9 C15H18BN3O2
5-(6-Chloro-3-pyridyl)pyridine-2-boronic acid pinacol ester 5-(6-Chloro-3-pyridyl)pyridine-2-boronic acid pinacol ester 1402227-50-2 C16H18BClN2O2
5-(cyclopropyl)-4-chloropyridine-3-boronic acid pinacol ester 5-(cyclopropyl)-4-chloropyridine-3-boronic acid pinacol ester 2223052-23-9 C14H19BClNO2
5-(Imidazol-1-yl)pyridine-3-boronic acid 5-(Imidazol-1-yl)pyridine-3-boronic acid 2225180-68-5 C8H8BN3O2
5-(iso-Propyl)furan-2-boronic acid 5-(iso-Propyl)furan-2-boronic acid 1694670-71-7 C7H11BO3
5-(Pyrimidin-2-yl)furan-2-boronic acid 5-(Pyrimidin-2-yl)furan-2-boronic acid 2225172-01-8 C8H7BN2O3
5-(TERT-BUTYL)PYRIDINE-3-BORONIC ACID 5-(TERT-BUTYL)PYRIDINE-3-BORONIC ACID 2225172-53-0 C9H14BNO2
5-Bromo-2-(2-chlorophenyl)pyrimidine 5-Bromo-2-(2-chlorophenyl)pyrimidine 1119089-12-1 C10H6BrClN2
5-Bromo-2-(4-cyanophenyl)pyrimidine 5-Bromo-2-(4-cyanophenyl)pyrimidine 183437-86-7 C11H6BrN3
5-Bromo-2-(methylethylamino)thiazole 5-Bromo-2-(methylethylamino)thiazole 959240-10-9 C6H9BrN2S
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