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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-(3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridin-2(1H)-one 1-(3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridin-2(1H)-one 2223039-67-4 C17H19BClNO3
1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-yl)pyridin-2(1H)-one 1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-yl)pyridin-2(1H)-one 1310384-95-2 C15H18BN3O3
1-(iso-Butyl)-1H-pyrrol-3-amine 1-(iso-Butyl)-1H-pyrrol-3-amine 1622839-74-0 C8H14N2
1,2-DI(PYRIMIDIN-4-YL)BENZENE 1,2-DI(PYRIMIDIN-4-YL)BENZENE 1622839-53-5 C14H10N4
1-Chloro-4-cyclopropylpyrido[4,3-d]pyridazine 1-Chloro-4-cyclopropylpyrido[4,3-d]pyridazine 1264037-94-6 C10H8ClN3
2-((propan-2-yl-d7)oxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-((propan-2-yl-d7)oxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241867-14-9 C14H22BNO3
2-(1,4-dioxan-2-yl)-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(1,4-dioxan-2-yl)-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223004-66-6 C16H24BNO5
2-(1,4-dioxan-2-yl)pyrimidin-4-amine 2-(1,4-dioxan-2-yl)pyrimidin-4-amine 1468630-06-9 C8H11N3O2
2-(1H-Pyrazol-1-yl)pyrimidine-5-boronic acid pinacol ester 2-(1H-Pyrazol-1-yl)pyrimidine-5-boronic acid pinacol ester 1449009-97-5 C13H17BN4O2
2-(1H-pyrrol-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-(1H-pyrrol-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2223038-44-4 C13H17BN2O2S
2-(2-Aminopropan-2-yl)pyridine-4-boronic acid pinacol ester 2-(2-Aminopropan-2-yl)pyridine-4-boronic acid pinacol ester 2223046-52-2 C14H23BN2O2
2-(2-methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2-(2-methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 1402227-23-9 C17H21BN2O3
2-(3,4-Difluorophenyl)pyridine-3-boronic acid 2-(3,4-Difluorophenyl)pyridine-3-boronic acid 2225154-96-9 C11H8BF2NO2
2-(3,5-Difluorophenyl)pyridine-3-boronic acid pinacol ester 2-(3,5-Difluorophenyl)pyridine-3-boronic acid pinacol ester 2223054-32-6 C17H18BF2NO2
2-(3-Chlorophenyl)pyridine-3-boronic acid 2-(3-Chlorophenyl)pyridine-3-boronic acid 2225178-61-8 C11H9BClNO2
2-(3-Fluorophenyl)pyridine-5-boronic acid pinacol ester 2-(3-Fluorophenyl)pyridine-5-boronic acid pinacol ester 2151860-06-7 C17H19BFNO2
2-(3-Methyl-1H-pyrazol-1-yl)pyridine-4-boronic acid 2-(3-Methyl-1H-pyrazol-1-yl)pyridine-4-boronic acid 2225172-82-5 C9H10BN3O2
2-(3-Thienyl)pyridine-3-boronic acid 2-(3-Thienyl)pyridine-3-boronic acid 2225154-61-8 C9H8BNO2S
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-6-d 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-6-d 2241867-63-8 C11H16BNO2
2-(4-cyclopropyl-3-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-(4-cyclopropyl-3-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1402227-01-3 C16H20BF3O2
2-(4-Hydroxy-piperidin-1-yl)-4,6-dichloropyrimidine 2-(4-Hydroxy-piperidin-1-yl)-4,6-dichloropyrimidine 1017781-93-9 C9H11Cl2N3O
2-(4-Pyridyl)pyridine-3-boronic acid pinacol ester 2-(4-Pyridyl)pyridine-3-boronic acid pinacol ester 2223027-62-9 C16H19BN2O2
2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-yl)pyridazin-3(2H)-one 2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-yl)pyridazin-3(2H)-one 2223012-36-8 C14H17BN4O3
2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)ethyl acetate 2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)ethyl acetate 2223038-79-5 C14H21BN2O4
2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-yl)pyridazin-3(2H)-one 2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-yl)pyridazin-3(2H)-one 2223050-22-2 C14H17BN4O3
2-(Cyclohexyl)pyridine-3-boronic acid 2-(Cyclohexyl)pyridine-3-boronic acid 2225173-19-1 C11H16BNO2
2-(CYCLOHEXYLOXY)PYRIMIDIN-5-AMINE 2-(CYCLOHEXYLOXY)PYRIMIDIN-5-AMINE 1250976-64-7 C10H15N3O
2-(Cyclopropyl)-5-(trifluoromethyl)pyridine-3-boronic acid 2-(Cyclopropyl)-5-(trifluoromethyl)pyridine-3-boronic acid 2225176-76-9 C9H9BF3NO2
2-(furan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-(furan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2096342-23-1 C13H16BNO3S
2-(iso-Butyl)pyridine-3-boronic acid 2-(iso-Butyl)pyridine-3-boronic acid 2225181-46-2 C9H14BNO2
2-(iso-Propyl)-5-(cyclopropyl)pyridine-3-boronic acid 2-(iso-Propyl)-5-(cyclopropyl)pyridine-3-boronic acid 2225174-52-5 C11H16BNO2
2-(iso-Propyl-5-cyanopyridine-3-boronic acid pinacol ester 2-(iso-Propyl-5-cyanopyridine-3-boronic acid pinacol ester 2223033-21-2 C15H21BN2O2
2-(methoxy-d3)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(methoxy-d3)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241867-16-1 C12H18BNO3
2-(methyl-d3)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(methyl-d3)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241867-19-4 C12H18BNO2
2-(N-Boc-piperidin-3-yl)pyrimidine-5-boronic acid pinacol ester 2-(N-Boc-piperidin-3-yl)pyrimidine-5-boronic acid pinacol ester 1350543-60-0 C20H32BN3O4
2-(N-Boc-Piperidin-4-yl)pyrimidine-5-boronic acid pinacol ester 2-(N-Boc-Piperidin-4-yl)pyrimidine-5-boronic acid pinacol ester 1350543-63-3 C20H32BN3O4
2-(n-Propyl)-6-(piperidin-3-yl)pyridine-4-boronic acid 2-(n-Propyl)-6-(piperidin-3-yl)pyridine-4-boronic acid 2225151-63-1 C13H21BN2O2
2-(n-Propyl)pyridine-3-boronic acid pinacol ester 2-(n-Propyl)pyridine-3-boronic acid pinacol ester 2223044-36-6 C14H22BNO2
2-(OXOLAN-3-YLOXY)PYRIMIDIN-5-AMINE 2-(OXOLAN-3-YLOXY)PYRIMIDIN-5-AMINE 1339758-57-4 C8H11N3O2
2-(sec-butyl)-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(sec-butyl)-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223003-48-1 C15H23BFNO2
2-(sec-Butyl)pyridine-4-boronic acid pinacol ester 2-(sec-Butyl)pyridine-4-boronic acid pinacol ester 2223009-20-7 C15H24BNO2
2-(tert-Butyl)-5-trifluoromethylpyridine-3-boronic acid pinacol ester 2-(tert-Butyl)-5-trifluoromethylpyridine-3-boronic acid pinacol ester 2223033-35-8 C16H23BF3NO2
2-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridine 2-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridine 2223035-50-3 C17H23BF3NO3
2,3-bis(methyl-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-4,6-d2 2,3-bis(methyl-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-4,6-d2 2241870-57-3 C13H12BD8NO2
2,4-Dibromo-5-(2-tolyl)pyridine 2,4-Dibromo-5-(2-tolyl)pyridine 1381933-44-3 C12H9Br2N
2,4-Dibromo-5-(n-propyl)pyridine 2,4-Dibromo-5-(n-propyl)pyridine 1314355-34-4 C8H9Br2N
2,5-Dibromo-4-(2-thienyl)pyridine 2,5-Dibromo-4-(2-thienyl)pyridine 1381933-54-5 C9H5Br2NS
2,5-Dibromo-4-(3-thienyl)pyridine 2,5-Dibromo-4-(3-thienyl)pyridine 1381943-39-0 C9H5Br2NS
2,5-Dibromo-4-(cyclohexyl)pyridine 2,5-Dibromo-4-(cyclohexyl)pyridine 1381933-49-8 C11H13Br2N
2,5-Dibromo-4-(morpholino)pyridine 2,5-Dibromo-4-(morpholino)pyridine 1381942-29-5 C9H10Br2N2O
2,6-Di(cyano)pyridine-4-boronic acid pinacol ester 2,6-Di(cyano)pyridine-4-boronic acid pinacol ester 2223048-32-4 C13H14BN3O2
2-[(5'-Methyl-5'-cyano)tetrahydrofuran-3-yl]pyridine-4-boronic acid pinacol ester 2-[(5'-Methyl-5'-cyano)tetrahydrofuran-3-yl]pyridine-4-boronic acid pinacol ester 2223005-44-3 C17H23BN2O3
2-[Pyridazin-3(2H)-one]-4-chloropyridine 2-[Pyridazin-3(2H)-one]-4-chloropyridine 1198154-97-0 C9H6ClN3O
2-AMINO-3-(CYCLOBUTOXY)PYRIDINE 2-AMINO-3-(CYCLOBUTOXY)PYRIDINE 1563533-61-8 C9H12N2O
2-Amino-3-bromo-5-(2-pyridyl)pyridine 2-Amino-3-bromo-5-(2-pyridyl)pyridine 1381936-54-4 C10H8BrN3
2-Amino-3-bromo-5-(3-trifluoromethylphenyl)pyridine 2-Amino-3-bromo-5-(3-trifluoromethylphenyl)pyridine 1381933-41-0 C12H8BrF3N2
2-Amino-3-bromo-5-(4-pyridyl)pyridine 2-Amino-3-bromo-5-(4-pyridyl)pyridine 79739-36-9 C10H8BrN3
2-Amino-4-(1H-2-methylimidazol-1-yl)-6-(iso-propyl)pyrimidine 2-Amino-4-(1H-2-methylimidazol-1-yl)-6-(iso-propyl)pyrimidine 1412958-80-5 C11H15N5
2-Amino-4-(1H-pyridin-2-one)-6-cyclopropylpyrimidine 2-Amino-4-(1H-pyridin-2-one)-6-cyclopropylpyrimidine 1412953-63-9 C12H12N4O
2-amino-4-(1H-pyrozol-1-yl)-6-cyclopropylpyrimidine 2-amino-4-(1H-pyrozol-1-yl)-6-cyclopropylpyrimidine 1412954-26-7 C10H11N5
2-amino-4-(2-methylpiperidin-1-yl)-6-(tert-butyl)pyrimidine 2-amino-4-(2-methylpiperidin-1-yl)-6-(tert-butyl)pyrimidine 1412959-53-5 C14H24N4
2-amino-4-(3-chlorophenyl)-6-cyclopropylpyrimidine 2-amino-4-(3-chlorophenyl)-6-cyclopropylpyrimidine 1412961-87-5 C13H12ClN3
2-Amino-4-(3-furyl)-6-methylpyrimidine 2-Amino-4-(3-furyl)-6-methylpyrimidine 1412958-56-5 C9H9N3O
2-Amino-4-(4-hydroxypiperidin-1-yl)pyrimidine 2-Amino-4-(4-hydroxypiperidin-1-yl)pyrimidine 1314354-13-6 C9H14N4O
2-Amino-4-(4-methylpiperidin-1-yl)-6-(iso-propyl)pyrimidine 2-Amino-4-(4-methylpiperidin-1-yl)-6-(iso-propyl)pyrimidine 1412960-47-4 C13H22N4
2-amino-4-(cyclopropyl)-6-(tert-butyl)pyrimidine 2-amino-4-(cyclopropyl)-6-(tert-butyl)pyrimidine 1412958-41-8 C11H17N3
2-Amino-4-(iso-propoxy)-6-(tert-butyl)pyrimidine 2-Amino-4-(iso-propoxy)-6-(tert-butyl)pyrimidine 1412957-36-8 C11H19N3O
2-Amino-4-(pyridin-3-yl)-6-(iso-propyl)pyrimidine 2-Amino-4-(pyridin-3-yl)-6-(iso-propyl)pyrimidine 1412953-61-7 C12H14N4
2-amino-4-(pyridin-4-yl)-6-cyclopropylpyrimidine 2-amino-4-(pyridin-4-yl)-6-cyclopropylpyrimidine 1412958-50-9 C12H12N4
2-Amino-4-bromo-5-(5-pyrimidyl)pyridine 2-Amino-4-bromo-5-(5-pyrimidyl)pyridine 1381942-79-5 C9H7BrN4
2-Amino-4-bromo-5-(iso-propyl)pyridine 2-Amino-4-bromo-5-(iso-propyl)pyridine 1357580-20-1 C8H11BrN2
2-Amino-4-chloro-5-(3-pyridyl)pyridine 2-Amino-4-chloro-5-(3-pyridyl)pyridine 1381943-08-3 C10H8ClN3
2-Amino-4-chloro-5-(4-methoxyphenyl)pyridine 2-Amino-4-chloro-5-(4-methoxyphenyl)pyridine 1381933-19-2 C12H11ClN2O
2-amino-4-cyclohexyl-6-cyclopropylpyrimidine 2-amino-4-cyclohexyl-6-cyclopropylpyrimidine 1622843-19-9 C13H19N3
2-amino-4-ethyl-6-(tert-butyl)pyrimidine 2-amino-4-ethyl-6-(tert-butyl)pyrimidine 1412954-35-8 C10H17N3
2-Amino-5-(2-pyridyl)pyrazine 2-Amino-5-(2-pyridyl)pyrazine 1044574-44-8 C9H8N4
2-Amino-5-(4-pyridyl)pyrazine 2-Amino-5-(4-pyridyl)pyrazine 1159819-60-9 C9H8N4
2-Amino-5-(5-methyl-2-pyridyl)pyrazine 2-Amino-5-(5-methyl-2-pyridyl)pyrazine 1159816-69-9 C10H10N4
2-Amino-5-(n-propyl)pyridine-4-boronic acid pinacol ester 2-Amino-5-(n-propyl)pyridine-4-boronic acid pinacol ester 2223050-17-5 C14H23BN2O2
2-Amino-5-bromo-4-(2-fluorophenyl)pyridine 2-Amino-5-bromo-4-(2-fluorophenyl)pyridine 1381935-88-1 C11H8BrFN2
2-Amino-5-bromo-4-(4-methoxyphenyl)pyridine 2-Amino-5-bromo-4-(4-methoxyphenyl)pyridine 1381936-93-1 C12H11BrN2O
2-Amino-5-bromo-4-(4-trifluoromethylphenyl)pyridine 2-Amino-5-bromo-4-(4-trifluoromethylphenyl)pyridine 1381942-48-8 C12H8BrF3N2
2-Amino-5-methyl-4-(cyclopropyl)pyridine 2-Amino-5-methyl-4-(cyclopropyl)pyridine 1318946-05-2 C9H12N2
2-AMINO-6-(1H-PYRROL-1-YL)PYRIDINE 2-AMINO-6-(1H-PYRROL-1-YL)PYRIDINE 1314356-47-2 C9H9N3
2-AMINO-6-(CYCLOBUTOXY)PYRIDINE 2-AMINO-6-(CYCLOBUTOXY)PYRIDINE 1103425-59-7 C9H12N2O
2-Bromo-3-(2-fluorophenyl)furan 2-Bromo-3-(2-fluorophenyl)furan 1227958-76-0 C10H6BrFO
2-Bromo-3-(2-methoxyphenyl)pyridine 2-Bromo-3-(2-methoxyphenyl)pyridine 335643-08-8 C12H10BrNO
2-Bromo-3-(2-thienyl)pyridine 2-Bromo-3-(2-thienyl)pyridine 1417519-37-9 C9H6BrNS
2-Bromo-3-(3-methoxyphenyl)thiophene 2-Bromo-3-(3-methoxyphenyl)thiophene 1227959-09-2 C11H9BrOS
2-Bromo-3-(3-tolyl)thiophene 2-Bromo-3-(3-tolyl)thiophene 1227958-74-8 C11H9BrS
2-Bromo-3-(4-trifluoromethylphenyl)furan 2-Bromo-3-(4-trifluoromethylphenyl)furan 1227959-33-2 C11H6BrF3O
2-Bromo-3-(iso-propyl)thiophene 2-Bromo-3-(iso-propyl)thiophene 29488-36-6 C7H9BrS
2-Bromo-3-(pyrimidin-5-yl)pyridine 2-Bromo-3-(pyrimidin-5-yl)pyridine 1417519-57-3 C9H6BrN3
2-Bromo-3-cyano-4-cyclopentylpyridine 2-Bromo-3-cyano-4-cyclopentylpyridine 1622839-28-4 C11H11BrN2
2-Bromo-3-fluoro-4-cyclopentylpyridine 2-Bromo-3-fluoro-4-cyclopentylpyridine 1622839-93-3 C10H11BrFN
2-Bromo-3-methoxycarbonyl-4-(n-propyl)pyridine 2-Bromo-3-methoxycarbonyl-4-(n-propyl)pyridine 1622843-25-7 C10H12BrNO2
2-Bromo-4-(1H-3-methylpyrozol-1-yl)-6-(iso-propyl)pyrimidine 2-Bromo-4-(1H-3-methylpyrozol-1-yl)-6-(iso-propyl)pyrimidine 1412960-90-7 C11H13BrN4
2-bromo-4-(1H-4-methylimidazol-1-yl)-6-cyclopropylpyrimidine 2-bromo-4-(1H-4-methylimidazol-1-yl)-6-cyclopropylpyrimidine 1412961-40-0 C11H11BrN4
2-Bromo-4-(1H-pyridin-2-one)-6-(tert-butyl)pyrimidine 2-Bromo-4-(1H-pyridin-2-one)-6-(tert-butyl)pyrimidine 1412958-18-9 C13H14BrN3O
2-Bromo-4-(1H-pyrozol-1-yl)-6-(iso-propyl)pyrimidine 2-Bromo-4-(1H-pyrozol-1-yl)-6-(iso-propyl)pyrimidine 1412957-61-9 C10H11BrN4
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