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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-hydroxy-4-(pyridin-2-yl)-6-cyclopropylpyrimidine 2-hydroxy-4-(pyridin-2-yl)-6-cyclopropylpyrimidine 1412960-30-5 C12H11N3O
2-Hydroxy-4-(pyridin-3-yl)-6-methylpyrimidine 2-Hydroxy-4-(pyridin-3-yl)-6-methylpyrimidine 1412953-37-7 C10H9N3O
2-Hydroxy-4-(tert-butoxy)-6-cyclopropylpyrimidine 2-Hydroxy-4-(tert-butoxy)-6-cyclopropylpyrimidine 1412955-20-4 C11H16N2O2
2-Hydroxy-4-cyclobutyl-6-(iso-propyl)pyrimidine 2-Hydroxy-4-cyclobutyl-6-(iso-propyl)pyrimidine 1412959-45-5 C11H16N2O
2-hydroxy-4-phenyl-6-(tert-butyl)pyrimidine 2-hydroxy-4-phenyl-6-(tert-butyl)pyrimidine 1412953-77-5 C14H16N2O
2-Hyroxy-4-(tert-butyl)-6-methylpyrimidine 2-Hyroxy-4-(tert-butyl)-6-methylpyrimidine 1412956-02-5 C9H14N2O
2-Iodo-6-(trifluoromethyl)pyridine-4-boronic acid 2-Iodo-6-(trifluoromethyl)pyridine-4-boronic acid 2225181-30-4 C6H4BF3INO2
2-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridine 2-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridine 2223011-82-1 C15H21BF3NO2
2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazole 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazole 2135512-71-7 C10H17BN2O2
2-Methyl-6-(piperidin-4-yl)pyridine-4-boronic acid 2-Methyl-6-(piperidin-4-yl)pyridine-4-boronic acid 2225171-83-3 C11H17BN2O2
2-Methyl-6-(tert-butyl)pyridine-3-boronic acid pinacol ester 2-Methyl-6-(tert-butyl)pyridine-3-boronic acid pinacol ester 2223037-38-3 C16H26BNO2
2-Trifluoromethyl-6-(piperidin-3-yl)pyridine-4-boronic acid 2-Trifluoromethyl-6-(piperidin-3-yl)pyridine-4-boronic acid 2225153-03-5 C11H14BF3N2O2
3-(2-Furyl)pyridine-2-boronic acid pinacol ester 3-(2-Furyl)pyridine-2-boronic acid pinacol ester 2223050-76-6 C15H18BNO3
3-(3-Thienyl)pyridine-2-boronic acid pinacol ester 3-(3-Thienyl)pyridine-2-boronic acid pinacol ester 2223036-13-1 C15H18BNO2S
3-(4-Trifluoromethylpyridin-2-yl)phenylboronic acid pinacol ester 3-(4-Trifluoromethylpyridin-2-yl)phenylboronic acid pinacol ester 2223046-15-7 C18H19BF3NO2
3-(6-Chloropyridin-2-yl)phenylboronic acid pinacol ester 3-(6-Chloropyridin-2-yl)phenylboronic acid pinacol ester 2223011-63-8 C17H19BClNO2
3-(CYCLOHEXYLOXY)PYRIDIN-2-AMINE 3-(CYCLOHEXYLOXY)PYRIDIN-2-AMINE 160656-01-9 C11H16N2O
3-(Cyclopentyl)pyridine-4-boronic acid 3-(Cyclopentyl)pyridine-4-boronic acid 2225180-02-7 C10H14BNO2
3-(methoxy-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(methoxy-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241875-19-2 C12H18BNO3
3-(n-Propyl)pyridine-2-boronic acid pinacol ester 3-(n-Propyl)pyridine-2-boronic acid pinacol ester 2223050-43-7 C14H22BNO2
3-(OXAN-4-YL)PYRIDIN-2-AMINE 3-(OXAN-4-YL)PYRIDIN-2-AMINE 1339883-30-5 C10H14N2O
3-(PYRIDIN-3-YL)PYRIDIN-2-AMINE 3-(PYRIDIN-3-YL)PYRIDIN-2-AMINE 163563-02-8 C10H9N3
3-(sec-Butyl)pyridine-2-boronic acid pinacol ester 3-(sec-Butyl)pyridine-2-boronic acid pinacol ester 2222996-09-8 C15H24BNO2
3-Amino-2-(1,4-dioxan-2-yl)pyridine 3-Amino-2-(1,4-dioxan-2-yl)pyridine 1622835-89-5 C9H12N2O2
3-Amino-6-(piperidino)pyridine-4-boronic acid pinacol ester 3-Amino-6-(piperidino)pyridine-4-boronic acid pinacol ester 2223012-79-9 C16H26BN3O2
3-Bromo-2-(cyclobutyl)pyridine-4-boronic acid pinacol ester 3-Bromo-2-(cyclobutyl)pyridine-4-boronic acid pinacol ester 2223036-30-2 C15H21BBrNO2
3-bromo-2-(sec-butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-bromo-2-(sec-butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2222997-09-1 C15H23BBrNO2
3-Bromo-2-fluoro-6-(oxan-2-yl)pyridine 3-Bromo-2-fluoro-6-(oxan-2-yl)pyridine 1622835-22-6 C10H11BrFNO
3-Bromo-2-fluoro-6-(sec-butyl)pyridine 3-Bromo-2-fluoro-6-(sec-butyl)pyridine 1622835-72-6 C9H11BrFN
3-Bromo-4-(3-furyl)-2-chloropyridine 3-Bromo-4-(3-furyl)-2-chloropyridine 1622842-73-2 C9H5BrClNO
3-BROMO-4-AMINO-6-(CYCLOHEXYL)PYRIDINE 3-BROMO-4-AMINO-6-(CYCLOHEXYL)PYRIDINE 1381937-91-2 C11H15BrN2
3-Bromo-4-chloro-6-cyclohexylpyridine 3-Bromo-4-chloro-6-cyclohexylpyridine 1353856-73-1 C11H13BrClN
3-Bromo-4-phenyl-2-pyridinecarbonitrile 3-Bromo-4-phenyl-2-pyridinecarbonitrile 1622838-89-4 C12H7BrN2
3-Bromo-6-(2-tolyl)pyridazine 3-Bromo-6-(2-tolyl)pyridazine 1086383-96-1 C11H9BrN2
3-Bromo-6-(3-fluorophenyl)pyridazine 3-Bromo-6-(3-fluorophenyl)pyridazine 1215072-05-1 C10H6BrFN2
3-Bromo-6-(5-aminopyridyl-3-yl)pyridazine 3-Bromo-6-(5-aminopyridyl-3-yl)pyridazine 1215072-34-6 C9H7BrN4
3-Bromo-6-(cyclohexyl)pyridazine 3-Bromo-6-(cyclohexyl)pyridazine 1086383-81-4 C10H13BrN2
3-Bromo-6-(sec-butyl)pyridazine 3-Bromo-6-(sec-butyl)pyridazine 1643543-19-4 C8H11BrN2
3-Ethylpyridine-2-boronic acid pinacol ester 3-Ethylpyridine-2-boronic acid pinacol ester 2223053-27-6 C13H20BNO2
3-Fluoro-4-(1H-pyridin-2-one)phenylboronic acid pinacol ester 3-Fluoro-4-(1H-pyridin-2-one)phenylboronic acid pinacol ester 2223050-37-9 C17H19BFNO3
3-Hydroxy-6-(2-cyclopropylpyrimidyl-5-yl)pyridazine 3-Hydroxy-6-(2-cyclopropylpyrimidyl-5-yl)pyridazine 1215072-75-5 C11H10N4O
3-Hydroxy-6-(6-fluoropyridyl-2-yl)pyridazine 3-Hydroxy-6-(6-fluoropyridyl-2-yl)pyridazine 1215071-47-8 C9H6FN3O
4-(1-N-Boc-3,6-Dihydro-2H-4-pyridyl)pyridine-2-boronic acid pinacol ester 4-(1-N-Boc-3,6-Dihydro-2H-4-pyridyl)pyridine-2-boronic acid pinacol ester 1402238-09-8 C21H31BN2O4
4-(2-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 4-(2-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 2223035-22-9 C19H28BNO3
4-(2-Fluorophenyl)-1,3,5-triazin-2-amine 4-(2-Fluorophenyl)-1,3,5-triazin-2-amine 1417518-18-3 C9H7FN4
4-(2-Methyl-4-fluorophenyl)-1,3,5-triazin-2-amine 4-(2-Methyl-4-fluorophenyl)-1,3,5-triazin-2-amine 1417519-23-3 C10H9FN4
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(thiophen-3-yl)pyridine 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(thiophen-3-yl)pyridine 1402240-68-9 C15H18BNO2S
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4'-bithiazole 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4'-bithiazole 2223033-28-9 C12H15BN2O2S2
4-(4-cyclopropyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 4-(4-cyclopropyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 2223032-84-4 C19H28BNO3
4-(4-fluoro-2-methylphenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(4-fluoro-2-methylphenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223038-63-7 C18H21BFNO2
4-(4-Trifluoromethylphenyl)-1,3,5-triazin-2-amine 4-(4-Trifluoromethylphenyl)-1,3,5-triazin-2-amine 873944-32-2 C10H7F3N4
4-(Cyclopentyl)furan-2-boronic acid 4-(Cyclopentyl)furan-2-boronic acid 2225155-72-4 C9H13BO3
4-(piperidin-1-yl-d10)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(piperidin-1-yl-d10)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241874-83-7 C16H25BN2O2
4-(tert-butyl)-6-hydroxy-2-(propan-2-yl)pyrimidine 4-(tert-butyl)-6-hydroxy-2-(propan-2-yl)pyrimidine 66700-35-4 C11H18N2O
4-(tetrahydro-2H-pyran-3-yl)pyrimidin-2-amine 4-(tetrahydro-2H-pyran-3-yl)pyrimidin-2-amine 2169660-80-2 C9H13N3O
4,4,5,5-tetramethyl-2-(4-(tetrahydrofuran-3-yl)thiophen-2-yl)-1,3,2-dioxaborolane 4,4,5,5-tetramethyl-2-(4-(tetrahydrofuran-3-yl)thiophen-2-yl)-1,3,2-dioxaborolane 2223006-85-5 C14H21BO3S
4,4,5,5-tetramethyl-2-(4-propylfuran-2-yl)-1,3,2-dioxaborolane 4,4,5,5-tetramethyl-2-(4-propylfuran-2-yl)-1,3,2-dioxaborolane 2223030-87-1 C13H21BO3
4,5-Dibromo-2-(4-tetrahydropyranyl)pyridine 4,5-Dibromo-2-(4-tetrahydropyranyl)pyridine 1381941-56-5 C10H11Br2NO
4,6-Dibromopyridine-2-boronic acid pinacol ester 4,6-Dibromopyridine-2-boronic acid pinacol ester 1402237-94-8 C11H14BBr2NO2
4-Amino-2-(1H-pyrazol-1-yl)pyrimidine 4-Amino-2-(1H-pyrazol-1-yl)pyrimidine 1314356-05-2 C7H7N5
4-Amino-2-(2-methoxyphenyl)pyrimidine 4-Amino-2-(2-methoxyphenyl)pyrimidine 1215072-96-0 C11H11N3O
4-Amino-2-(iso-propyl)-6-(1H-4-methylpyrozol-1-yl)pyrimidine 4-Amino-2-(iso-propyl)-6-(1H-4-methylpyrozol-1-yl)pyrimidine 1412959-12-6 C11H15N5
4-Amino-2-(iso-propyl)-6-(2-furyl)pyrimidine 4-Amino-2-(iso-propyl)-6-(2-furyl)pyrimidine 1250216-11-5 C11H13N3O
4-Amino-2-(iso-propyl)-6-(pyrrolidin-1-yl)pyrimidine 4-Amino-2-(iso-propyl)-6-(pyrrolidin-1-yl)pyrimidine 1412958-29-2 C11H18N4
4-amino-2-cyclopropyl-6-cyclopentylpyrimidine 4-amino-2-cyclopropyl-6-cyclopentylpyrimidine 1412954-36-9 C12H17N3
4-Amino-2-fluoro-6-(piperidin-4-yl)pyridine 4-Amino-2-fluoro-6-(piperidin-4-yl)pyridine 1622843-08-6 C10H14FN3
4-amino-2-methyl-6-(4-methylpiperidin-1-yl)pyrimidine 4-amino-2-methyl-6-(4-methylpiperidin-1-yl)pyrimidine 1412957-54-0 C11H18N4
4-Amino-2-methylpyrimidine-5-boronic acid pinacol ester 4-Amino-2-methylpyrimidine-5-boronic acid pinacol ester 2223040-93-3 C11H18BN3O2
4-Amino-6-(1H-pyridin-2-one)pyrimidine 4-Amino-6-(1H-pyridin-2-one)pyrimidine 1314356-39-2 C9H8N4O
4-Amino-6-(3-chlorophenyl)-2-(iso-propyl)pyrimidine 4-Amino-6-(3-chlorophenyl)-2-(iso-propyl)pyrimidine 1307636-21-0 C13H14ClN3
4-Amino-6-(tert-butoxy)-2-methylpyrimidine 4-Amino-6-(tert-butoxy)-2-methylpyrimidine 1412955-87-3 C9H15N3O
4-Bromo-2-(1H-pyridin-2-one)pyrimidine 4-Bromo-2-(1H-pyridin-2-one)pyrimidine 959241-24-8 C9H6BrN3O
4-Bromo-2-(3-thienyl)pyrimidine 4-Bromo-2-(3-thienyl)pyrimidine 1086381-97-6 C8H5BrN2S
4-Bromo-2-(iso-propyl)-6-(2-furyl)pyrimidine 4-Bromo-2-(iso-propyl)-6-(2-furyl)pyrimidine 1412953-78-6 C11H11BrN2O
4-Bromo-2-(iso-propyl)-6-(pyrimidin-5-yl)pyrimidine 4-Bromo-2-(iso-propyl)-6-(pyrimidin-5-yl)pyrimidine 1412953-79-7 C11H11BrN4
4-Bromo-2-(n-propyl)pyrimidine 4-Bromo-2-(n-propyl)pyrimidine 1086381-81-8 C7H9BrN2
4-Bromo-2-acetoxythiazole 4-Bromo-2-acetoxythiazole 1264035-93-9 C5H4BrNO2S
4-Bromo-2-amino-5-(3-pyridyl)pyridine 4-Bromo-2-amino-5-(3-pyridyl)pyridine 1381933-42-1 C10H8BrN3
4-Bromo-2-cyclopropyl-6-(1H-pyrrol-1-yl)pyrimidine 4-Bromo-2-cyclopropyl-6-(1H-pyrrol-1-yl)pyrimidine 1412957-42-6 C11H10BrN3
4-Bromo-2-cyclopropyl-6-(2-methylpiperidin-1-yl)pyrimidine 4-Bromo-2-cyclopropyl-6-(2-methylpiperidin-1-yl)pyrimidine 1412962-00-5 C13H18BrN3
4-Bromo-2-cyclopropyl-6-(4-pyridyl)pyrimidine 4-Bromo-2-cyclopropyl-6-(4-pyridyl)pyrimidine 1412954-52-9 C12H10BrN3
4-bromo-2-cyclopropyl-6-(iso-propyl)pyrimidine 4-bromo-2-cyclopropyl-6-(iso-propyl)pyrimidine 1412958-15-6 C10H13BrN2
4-Bromo-2-fluoro-6-(oxan-4-yl)pyridine 4-Bromo-2-fluoro-6-(oxan-4-yl)pyridine 1622843-20-2 C10H11BrFNO
4-Bromo-2-methyl-6-(iso-propoxy)pyrimidine 4-Bromo-2-methyl-6-(iso-propoxy)pyrimidine 1412955-55-5 C8H11BrN2O
4-Bromo-2-methyl-6-(piperidin-4-yl)pyridine 4-Bromo-2-methyl-6-(piperidin-4-yl)pyridine 1622843-48-4 C11H15BrN2
4-Bromo-3-cyclopentylpyridine 4-Bromo-3-cyclopentylpyridine 1314356-10-9 C10H12BrN
4-Bromo-3-fluoro-6-(n-propyl)pyridine 4-Bromo-3-fluoro-6-(n-propyl)pyridine 1643576-65-1 C8H9BrFN
4-Bromo-5-(2-aminopropan-2-yl)thiazole 4-Bromo-5-(2-aminopropan-2-yl)thiazole 1563531-01-0 C6H9BrN2S
4-Bromo-5-methylpyridine-2-boronic acid pinacol ester 4-Bromo-5-methylpyridine-2-boronic acid pinacol ester 1402172-58-0 C12H17BBrNO2
4-bromo-6-(2-fluorophenyl)-2-methylpyrimidine 4-bromo-6-(2-fluorophenyl)-2-methylpyrimidine 1412957-66-4 C11H8BrFN2
4-Bromo-6-(N-phenylmethylene)pyridine-2-boronic acid pinacol ester 4-Bromo-6-(N-phenylmethylene)pyridine-2-boronic acid pinacol ester 2223056-48-0 C18H20BBrN2O2
4-bromo-6-cyclohexyl-2-(propan-2-yl)pyrimidine 4-bromo-6-cyclohexyl-2-(propan-2-yl)pyrimidine 1412955-74-8 C13H19BrN2
4-Chloro-2-(3-aminophenyl)pyrimidine 4-Chloro-2-(3-aminophenyl)pyrimidine 1215073-47-4 C10H8ClN3
4-Chloro-2-(4-tolyl)pyrimidine 4-Chloro-2-(4-tolyl)pyrimidine 1156238-11-7 C11H9ClN2
4-Chloro-2-(cyclohexyl)pyrimidine 4-Chloro-2-(cyclohexyl)pyrimidine 1155593-86-4 C10H13ClN2
4-chloro-2-(iso-propyl)-6-(1H-pyrozol-1-yl)pyrimidine 4-chloro-2-(iso-propyl)-6-(1H-pyrozol-1-yl)pyrimidine 1412960-66-7 C10H11ClN4
4-chloro-2-(iso-propyl)-6-(2-tolyl)pyrimidine 4-chloro-2-(iso-propyl)-6-(2-tolyl)pyrimidine 1412956-14-9 C14H15ClN2
4-chloro-2-(iso-propyl)-6-morpholinopyrimidine 4-chloro-2-(iso-propyl)-6-morpholinopyrimidine 22201-85-0 C11H16ClN3O
4-Chloro-2-cyclopropyl-6-(3-chlorophenyl)pyrimidine 4-Chloro-2-cyclopropyl-6-(3-chlorophenyl)pyrimidine 1412953-11-7 C13H10Cl2N2
4-Chloro-5-bromo-2-(tert-butoxy)pyridine 4-Chloro-5-bromo-2-(tert-butoxy)pyridine 1353855-08-9 C9H11BrClNO
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