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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-Chloro-4-(3-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine 2-Chloro-4-(3-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine 1248082-73-6 C9H9ClN4
2-Chloro-4-(3-methylpiperidin-1-yl)-6-(iso-propyl)pyrimidine 2-Chloro-4-(3-methylpiperidin-1-yl)-6-(iso-propyl)pyrimidine 1412953-87-7 C13H20ClN3
2-chloro-4-(4-chlorophenyl)-6-cyclopropylpyrimidine 2-chloro-4-(4-chlorophenyl)-6-cyclopropylpyrimidine 951231-17-7 C13H10Cl2N2
2-Chloro-4-(4-methoxyphenyl)-1,3,5-triazine 2-Chloro-4-(4-methoxyphenyl)-1,3,5-triazine 1417518-41-2 C10H8ClN3O
2-Chloro-4-(4-tetrahydropyranyl)-6-(iso-propyl)pyrimidine 2-Chloro-4-(4-tetrahydropyranyl)-6-(iso-propyl)pyrimidine 1412961-00-2 C12H17ClN2O
2-chloro-4-(cyclopentyl)-6-cyclopropylpyrimidine 2-chloro-4-(cyclopentyl)-6-cyclopropylpyrimidine 1412961-35-3 C12H15ClN2
2-Chloro-4-(n-propyl)-6-(iso-propyl)pyrimidine 2-Chloro-4-(n-propyl)-6-(iso-propyl)pyrimidine 1412954-92-7 C10H15ClN2
2-Chloro-4-(pyridin-4-yl)-6-(iso-propyl)pyrimidine 2-Chloro-4-(pyridin-4-yl)-6-(iso-propyl)pyrimidine 1412958-93-0 C12H12ClN3
2-chloro-4-(pyrimidin-5-yl)-6-cyclopropylpyrimidine 2-chloro-4-(pyrimidin-5-yl)-6-cyclopropylpyrimidine 1412956-68-3 C11H9ClN4
2-Chloro-4-(tert-butyl)-1,3,5-triazine 2-Chloro-4-(tert-butyl)-1,3,5-triazine 1417517-78-2 C7H10ClN3
2-chloro-4,6-dicyclopropylpyrimidine 2-chloro-4,6-dicyclopropylpyrimidine 1361300-37-9 C10H11ClN2
2-Chloro-4-cyclopropyl-6-(iso-propyl)pyrimidine 2-Chloro-4-cyclopropyl-6-(iso-propyl)pyrimidine 1412960-73-6 C10H13ClN2
2-Chloro-4-ethyl-6-cyclopropylpyrimidine 2-Chloro-4-ethyl-6-cyclopropylpyrimidine 121553-41-1 C9H11ClN2
2-chloro-4-phenyl-6-cyclopropylpyrimidine 2-chloro-4-phenyl-6-cyclopropylpyrimidine 1412961-83-1 C13H11ClN2
2-cyclobutyl-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-cyclobutyl-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223048-72-2 C15H21BFNO2
2-cyclobutyl-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-cyclobutyl-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223033-76-7 C15H21BFNO2
2-cyclopentyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2-cyclopentyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2223011-61-6 C15H23BN2O2
2-Cyclopropyl-5-trifluoromethylpyridine-3-boronic acid pinacol ester 2-Cyclopropyl-5-trifluoromethylpyridine-3-boronic acid pinacol ester 2223011-33-2 C15H19BF3NO2
2-ethyl-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-ethyl-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223035-29-6 C13H19BFNO2
2-Fluoro-3-bromo-4-cyclohexylpyridine 2-Fluoro-3-bromo-4-cyclohexylpyridine 1622843-26-8 C11H13BrFN
2-Fluoro-6-(3-bromophenyl)pyridine 2-Fluoro-6-(3-bromophenyl)pyridine 1563529-39-4 C11H7BrFN
2-Fluoro-6-(cyclohexyl)pyridine-3-boronic acid pinacol ester 2-Fluoro-6-(cyclohexyl)pyridine-3-boronic acid pinacol ester 2223037-17-8 C17H25BFNO2
2-Fluoro-6-(n-propyl)pyridine-3-boronic acid pinacol ester 2-Fluoro-6-(n-propyl)pyridine-3-boronic acid pinacol ester 2223050-03-9 C14H21BFNO2
2-fluoro-6-(tetrahydro-2H-pyran-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-fluoro-6-(tetrahydro-2H-pyran-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223009-68-3 C16H23BFNO3
2-fluoro-6-(tetrahydrofuran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-fluoro-6-(tetrahydrofuran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223003-97-0 C15H21BFNO3
2-Fluoro-6-ethylpyridine-3-boronic acid pinacol ester 2-Fluoro-6-ethylpyridine-3-boronic acid pinacol ester 2223044-40-2 C13H19BFNO2
2-Hydroxy-3-(2-methoxyphenyl)pyridine 2-Hydroxy-3-(2-methoxyphenyl)pyridine 143074-70-8 C12H11NO2
2-Hydroxy-3-(3,4-difluorophenyl)pyridine 2-Hydroxy-3-(3,4-difluorophenyl)pyridine 1261937-37-4 C11H7F2NO
2-Hydroxy-3-(n-propyl)pyridine 2-Hydroxy-3-(n-propyl)pyridine 1093656-00-8 C8H11NO
2-Hydroxy-3-(thiazol-4-yl)pyridine 2-Hydroxy-3-(thiazol-4-yl)pyridine 1417519-41-5 C8H6N2OS
2-hydroxy-4-(2-fluorophenyl)-6-cyclopropylpyrimidine 2-hydroxy-4-(2-fluorophenyl)-6-cyclopropylpyrimidine 1412961-65-9 C13H11FN2O
2-hydroxy-4-(2-furyl)-6-cyclopropylpyrimidine 2-hydroxy-4-(2-furyl)-6-cyclopropylpyrimidine 1412957-86-8 C11H10N2O2
2-Hydroxy-4-(2-tolyl)pyrimidine 2-Hydroxy-4-(2-tolyl)pyrimidine 1159816-96-2 C11H10N2O
2-Hydroxy-4-(3,4-difluorophenyl)pyrimidine 2-Hydroxy-4-(3,4-difluorophenyl)pyrimidine 1159820-19-5 C10H6F2N2O
2-Hydroxy-4-(3-thienyl)-6-methylpyrimidine 2-Hydroxy-4-(3-thienyl)-6-methylpyrimidine 1412952-88-5 C9H8N2OS
2-Hydroxy-4-(4-ethylphenyl)pyrimidine 2-Hydroxy-4-(4-ethylphenyl)pyrimidine 1159817-36-3 C12H12N2O
2-Hydroxy-4-(cyclobutyl)pyrimidine 2-Hydroxy-4-(cyclobutyl)pyrimidine 1215074-18-2 C8H10N2O
2-Hydroxy-4-(cyclopentyl)pyrimidine 2-Hydroxy-4-(cyclopentyl)pyrimidine 1215074-03-5 C9H12N2O
2-Hydroxy-4-(piperidin-1-yl)-6-methylpyrimidine 2-Hydroxy-4-(piperidin-1-yl)-6-methylpyrimidine 62968-18-7 C10H15N3O
2-Hydroxy-4-(pyridin-3-yl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(pyridin-3-yl)-6-(iso-propyl)pyrimidine 1412953-25-3 C12H13N3O
2-Hydroxy-4-(pyrrolidin-1-yl)-6-methylpyrimidine 2-Hydroxy-4-(pyrrolidin-1-yl)-6-methylpyrimidine 1412960-88-3 C9H13N3O
2-Hydroxy-4,6-di(tert-butyl)pyrimidine 2-Hydroxy-4,6-di(tert-butyl)pyrimidine 60546-02-3 C12H20N2O
2-Hydroxy-4-morpholino-6-cyclopropylpyrimidine 2-Hydroxy-4-morpholino-6-cyclopropylpyrimidine 1412954-80-3 C11H15N3O2
2-Iodo-6-(N-Boc-piperidin-3-yl)pyridine-4-boronic acid pinacol esier 2-Iodo-6-(N-Boc-piperidin-3-yl)pyridine-4-boronic acid pinacol esier 2223004-22-4 C21H32BIN2O4
2-isopropoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-isopropoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 1350755-35-9 C12H20BNO3S
2-propyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-propyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2223052-84-2 C12H20BNO2S
3-(1,4-Dioxan-2-yl)pyridine-4-boronic acid pinacol ester 3-(1,4-Dioxan-2-yl)pyridine-4-boronic acid pinacol ester 2222996-04-3 C15H22BNO4
3-(3-Fluorophenyl)pyridine-2-boronic acid pinacol ester 3-(3-Fluorophenyl)pyridine-2-boronic acid pinacol ester 2223049-30-5 C17H19BFNO2
3-(5-Fluoropyridin-2-yl)phenylboronic acid pinacol ester 3-(5-Fluoropyridin-2-yl)phenylboronic acid pinacol ester 2223045-56-3 C17H19BFNO2
3-(n-Propyl)pyridine-4-boronic acid pinacol ester 3-(n-Propyl)pyridine-4-boronic acid pinacol ester 2223027-20-9 C14H22BNO2
3-(Pyridin-2-yl)-5-bromophenylboronic acid pinacol ester 3-(Pyridin-2-yl)-5-bromophenylboronic acid pinacol ester 2223051-78-1 C17H19BBrNO2
3-(sec-butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(sec-butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 1426957-77-8 C15H24BNO2
3-(Thiazol-4-yl)pyridine-2-boronic acid pinacol ester 3-(Thiazol-4-yl)pyridine-2-boronic acid pinacol ester 2223037-50-9 C14H17BN2O2S
3,4-Dibromo-6-cyclopentylpyridine 3,4-Dibromo-6-cyclopentylpyridine 1353854-59-7 C10H11Br2N
3-[4-(Methoxycarbonyl)pyridin-2-yl]phenylboronic acid pinacol ester 3-[4-(Methoxycarbonyl)pyridin-2-yl]phenylboronic acid pinacol ester 2223049-26-9 C19H22BNO4
3-Amino-6-(2-thienyl)pyridazine 3-Amino-6-(2-thienyl)pyridazine 105538-01-0 C8H7N3S
3-Amino-6-(3-methylpiperidin-1-yl)pyridazine 3-Amino-6-(3-methylpiperidin-1-yl)pyridazine 1314356-46-1 C10H16N4
3-Bromo-1-(sec-butyl)-1H-pyrrole 3-Bromo-1-(sec-butyl)-1H-pyrrole 1622834-97-2 C8H12BrN
3-Bromo-2-(cyclopentyl)pyridine-4-boronic acid pinacol ester 3-Bromo-2-(cyclopentyl)pyridine-4-boronic acid pinacol ester 2223012-70-0 C16H23BBrNO2
3-Bromo-4-(2-furyl)-2-pyridinecarbonitrile 3-Bromo-4-(2-furyl)-2-pyridinecarbonitrile 1622838-91-8 C10H5BrN2O
3-Bromo-4-(oxan-4-yl)-2-pyridinecarbonitrile 3-Bromo-4-(oxan-4-yl)-2-pyridinecarbonitrile 1622839-39-7 C11H11BrN2O
3-Bromo-4-cyclopentyl-2-chloropyridine 3-Bromo-4-cyclopentyl-2-chloropyridine 1622840-83-8 C10H11BrClN
3-Bromo-6-(2-cyclopropylpyrimidyl-5-yl)pyridazine 3-Bromo-6-(2-cyclopropylpyrimidyl-5-yl)pyridazine 1215071-46-7 C11H9BrN4
3-Bromo-6-(2-methylpiperidino)pyridazine 3-Bromo-6-(2-methylpiperidino)pyridazine 1027513-27-4 C10H14BrN3
3-Bromo-6-(3,4-difluorophenyl)pyridazine 3-Bromo-6-(3,4-difluorophenyl)pyridazine 1215074-24-0 C10H5BrF2N2
3-Bromo-6-(4-methylpiperidino)pyridazine 3-Bromo-6-(4-methylpiperidino)pyridazine 1027513-18-3 C10H14BrN3
3-Bromo-6-(6-fluoropyridyl-2-yl)pyridazine 3-Bromo-6-(6-fluoropyridyl-2-yl)pyridazine 1215073-62-3 C9H5BrFN3
3-Bromo-6-(n-propoxy)pyridazine 3-Bromo-6-(n-propoxy)pyridazine 17321-31-2 C7H9BrN2O
3-Bromo-6-[pyridazin-3(2H)-one]pyridine 3-Bromo-6-[pyridazin-3(2H)-one]pyridine 948846-80-8 C9H6BrN3O
3-Hydroxy-6-(2-trifluoromethylphenyl)pyridazine 3-Hydroxy-6-(2-trifluoromethylphenyl)pyridazine 1154598-40-9 C11H7F3N2O
3-Methyl-2-(sec-butyl)pyridine-4-boronic acid pinacol ester 3-Methyl-2-(sec-butyl)pyridine-4-boronic acid pinacol ester 2223008-95-3 C16H26BNO2
4-(1,4-Dioxan-2-yl)pyridine-3-boronic acid pinacol ester 4-(1,4-Dioxan-2-yl)pyridine-3-boronic acid pinacol ester 2223006-80-0 C15H22BNO4
4-(2-Pyridyl)thiazole-5-boronic acid pinacol ester 4-(2-Pyridyl)thiazole-5-boronic acid pinacol ester 2223011-15-0 C14H17BN2O2S
4-(3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 4-(3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 1893410-04-2 C16H23BBrNO3
4-(3-Furyl)-1,3,5-triazin-2-amine 4-(3-Furyl)-1,3,5-triazin-2-amine 1343931-27-0 C7H6N4O
4-(3-Pyridyl)thiazole-5-boronic acid pinacol ester 4-(3-Pyridyl)thiazole-5-boronic acid pinacol ester 2223050-58-4 C14H17BN2O2S
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(o-tolyl)thiazole 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(o-tolyl)thiazole 1402173-88-9 C16H20BNO2S
4-(4-Bromopyridin-2-yl)furan-2-boronic acid pinacol ester 4-(4-Bromopyridin-2-yl)furan-2-boronic acid pinacol ester 2223035-86-5 C15H17BBrNO3
4-(4-Pyridyl)thiazole-5-boronic acid pinacol ester 4-(4-Pyridyl)thiazole-5-boronic acid pinacol ester 2223054-18-8 C14H17BN2O2S
4-(5-cyclopropyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 4-(5-cyclopropyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 2223042-90-6 C19H28BNO3
4-(5-Pyrimidyl)-1,3,5-triazin-2-amine 4-(5-Pyrimidyl)-1,3,5-triazin-2-amine 1417518-66-1 C7H6N6
4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)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)morpholine-2,2,3,3,5,5,6,6-d8 2241872-10-4 C15H23BN2O3
4-(Cyclopentyl)pyridine-3-boronic acid pinacol ester 4-(Cyclopentyl)pyridine-3-boronic acid pinacol ester 2223027-49-2 C16H24BNO2
4-(tert-Butyl)-1,3,5-triazin-2-amine 4-(tert-Butyl)-1,3,5-triazin-2-amine 114640-81-2 C7H12N4
4-(tert-Butyl)pyridine-3-boronic acid pinacol ester 4-(tert-Butyl)pyridine-3-boronic acid pinacol ester 2223012-99-3 C15H24BNO2
4,4,5,5-tetramethyl-2-(4-(tetrahydrofuran-2-yl)furan-2-yl)-1,3,2-dioxaborolane 4,4,5,5-tetramethyl-2-(4-(tetrahydrofuran-2-yl)furan-2-yl)-1,3,2-dioxaborolane 2223005-80-7 C14H21BO4
4,4,5,5-tetramethyl-2-(5-(thiophen-2-yl)furan-2-yl)-1,3,2-dioxaborolane 4,4,5,5-tetramethyl-2-(5-(thiophen-2-yl)furan-2-yl)-1,3,2-dioxaborolane 2223032-93-5 C14H17BO3S
4,6-Dichloro-2-(3,5-difluorophenyl)pyrimidine 4,6-Dichloro-2-(3,5-difluorophenyl)pyrimidine 1188237-69-5 C10H4Cl2F2N2
4-Amino-2-(cyclopentyl)pyrimidine-5-boronic acid pinacol ester 4-Amino-2-(cyclopentyl)pyrimidine-5-boronic acid pinacol ester 2223033-87-0 C15H24BN3O2
4-Amino-2-(iso-propyl)-6-(1H-2-methylimidazol-1-yl)pyrimidine 4-Amino-2-(iso-propyl)-6-(1H-2-methylimidazol-1-yl)pyrimidine 1412958-96-3 C11H15N5
4-Amino-2-(iso-propyl)-6-(3-thienyl)pyrimidine 4-Amino-2-(iso-propyl)-6-(3-thienyl)pyrimidine 1412960-55-4 C11H13N3S
4-amino-2-(iso-propyl)-6-(pyridin-3-yl)-pyrimidine 4-amino-2-(iso-propyl)-6-(pyridin-3-yl)-pyrimidine 1412953-72-0 C12H14N4
4-Amino-2-cyclopropyl-6-(1H-pyridin-2-one)pyrimidine 4-Amino-2-cyclopropyl-6-(1H-pyridin-2-one)pyrimidine 1412960-93-0 C12H12N4O
4-Amino-2-cyclopropyl-6-(2-methylpiperidin-1-yl)pyrimidine 4-Amino-2-cyclopropyl-6-(2-methylpiperidin-1-yl)pyrimidine 1412957-33-5 C13H20N4
4-Amino-2-cyclopropyl-6-(morpholino)pyrimidine 4-Amino-2-cyclopropyl-6-(morpholino)pyrimidine 1412958-85-0 C11H16N4O
4-Amino-2-cyclopropyl-6-(tert-butyl)pyrimidine 4-Amino-2-cyclopropyl-6-(tert-butyl)pyrimidine 1249172-82-4 C11H17N3
4-amino-2-methyl-6-(1H-imidazol-1-yl)pyrimidine 4-amino-2-methyl-6-(1H-imidazol-1-yl)pyrimidine 1412958-82-7 C8H9N5
4-AMINO-3-BROMO-6-METHYLPYRIDINE 4-AMINO-3-BROMO-6-METHYLPYRIDINE 1381944-15-5 C12H11BrN2
4-Amino-5-(4-pyridyl)thiazole 4-Amino-5-(4-pyridyl)thiazole 1368937-00-1 C8H7N3S
4-Amino-6-(4-methyl-1H-pyrazol-1-yl)pyrimidine 4-Amino-6-(4-methyl-1H-pyrazol-1-yl)pyrimidine 1314353-52-0 C8H9N5
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