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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-Bromo-5-(3-fluorophenyl)furan 2-Bromo-5-(3-fluorophenyl)furan 1412954-24-5 C10H6BrFO
2-Bromo-5-(methylethylamino)furan 2-Bromo-5-(methylethylamino)furan 1622834-40-5 C7H10BrNO
2-Bromo-5-(sec-Butyl)thiazole 2-Bromo-5-(sec-Butyl)thiazole 1412957-75-5 C7H10BrNS
2-Bromo-5-cyclohexylpyridine-4-boronic acid pinacol ester 2-Bromo-5-cyclohexylpyridine-4-boronic acid pinacol ester 1402238-01-0 C17H25BBrNO2
2-Bromo-6-(3-thienyl)pyridine-4-boronic acid pinacol ester 2-Bromo-6-(3-thienyl)pyridine-4-boronic acid pinacol ester 2223044-73-1 C15H17BBrNO2S
2-Bromo-6-(4-pyridyl)pyridine-4-boronic acid pinacol ester 2-Bromo-6-(4-pyridyl)pyridine-4-boronic acid pinacol ester 2223041-45-8 C16H18BBrN2O2
2-Bromo-6-(N-Boc-piperidin-3-yl)pyridine-4-boronic acid  pinacol esier 2-Bromo-6-(N-Boc-piperidin-3-yl)pyridine-4-boronic acid pinacol esier 2223004-52-0 C21H32BBrN2O4
2-Bromo-6-(oxan-2-yl)pyridine-4-boronic acid pinacol ester 2-Bromo-6-(oxan-2-yl)pyridine-4-boronic acid pinacol ester 2223006-64-0 C16H23BBrNO3
2-Bromo-6-phenylpyridine-4-boronic acid pinacol ester 2-Bromo-6-phenylpyridine-4-boronic acid pinacol ester 2223011-92-3 C17H19BBrNO2
2-Chloro-3-(3-methoxyphenyl)pyridine 2-Chloro-3-(3-methoxyphenyl)pyridine 31557-58-1 C12H10ClNO
2-Chloro-3-(4-methoxyphenyl)pyridine 2-Chloro-3-(4-methoxyphenyl)pyridine 1225999-06-3 C12H10ClNO
2-Chloro-3-(tert-butyl)pyridine 2-Chloro-3-(tert-butyl)pyridine 102236-58-8 C9H12ClN
2-Chloro-3-cyano-4-(tert-butyl)pyridine 2-Chloro-3-cyano-4-(tert-butyl)pyridine 1622843-49-5 C10H11ClN2
2-Chloro-4-(2-chlorophenyl)-6-methylpyrimidine 2-Chloro-4-(2-chlorophenyl)-6-methylpyrimidine 1412958-49-6 C11H8Cl2N2
2-Chloro-4-(2-methyl-4-fluorophenyl)-1,3,5-triazine 2-Chloro-4-(2-methyl-4-fluorophenyl)-1,3,5-triazine 1417518-34-3 C10H7ClFN3
2-chloro-4-(2-methylpiperidin-1-yl)-6-(tert-butyl)pyrimidine 2-chloro-4-(2-methylpiperidin-1-yl)-6-(tert-butyl)pyrimidine 1412956-74-1 C14H22ClN3
2-Chloro-4-(2-trifluoromethylphenyl)-1,3,5-triazine 2-Chloro-4-(2-trifluoromethylphenyl)-1,3,5-triazine 1417519-73-3 C10H5ClF3N3
2-Chloro-4-(3,4-difluorophenyl)-1,3,5-triazine 2-Chloro-4-(3,4-difluorophenyl)-1,3,5-triazine 1417518-33-2 C9H4ClF2N3
2-chloro-4-(3-methylpiperidin-1-yl)-6-(tert-butyl)pyrimidine 2-chloro-4-(3-methylpiperidin-1-yl)-6-(tert-butyl)pyrimidine 1412954-46-1 C14H22ClN3
2-Chloro-4-(4-cyclobutoxy)-1,3,5-triazine 2-Chloro-4-(4-cyclobutoxy)-1,3,5-triazine 1417518-72-9 C7H8ClN3O
2-Chloro-4-(4-methyl-1H-imidazol-1-yl)-6-methylpyrimidine 2-Chloro-4-(4-methyl-1H-imidazol-1-yl)-6-methylpyrimidine 1412961-04-6 C9H9ClN4
2-CHLORO-4-(4-METHYLPIPERIDIN-1-YL)PYRIMIDINE 2-CHLORO-4-(4-METHYLPIPERIDIN-1-YL)PYRIMIDINE 404826-27-3 C10H14ClN3
2-chloro-4-(4-tetrahydropyranyl)-6-(tert-butyl)pyrimidine 2-chloro-4-(4-tetrahydropyranyl)-6-(tert-butyl)pyrimidine 1412957-93-7 C13H19ClN2O
2-chloro-4-(n-propyl)-6-(tert-butyl)pyrimidine 2-chloro-4-(n-propyl)-6-(tert-butyl)pyrimidine 1412953-96-8 C11H17ClN2
2-Chloro-4-(piperidin-1-yl)-6-(iso-propyl)pyrimidine 2-Chloro-4-(piperidin-1-yl)-6-(iso-propyl)pyrimidine 1412953-88-8 C12H18ClN3
2-chloro-4-(pyridin-4-yl)-6-(tert-butyl)pyrimidine 2-chloro-4-(pyridin-4-yl)-6-(tert-butyl)pyrimidine 1412954-61-0 C13H14ClN3
2-Chloro-4-(pyrimidin-5-yl)-6-methylpyrimidine 2-Chloro-4-(pyrimidin-5-yl)-6-methylpyrimidine 1412959-16-0 C9H7ClN4
2-Chloro-4-(tert-butyl)-6-methylpyrimidine 2-Chloro-4-(tert-butyl)-6-methylpyrimidine 1622844-14-7 C9H13ClN2
2-Chloro-4,6-diisopropylpyrimidine 2-Chloro-4,6-diisopropylpyrimidine 1346170-80-6 C10H15ClN2
2-chloro-5-(1,4-dioxan-2-yl)pyrimidine 2-chloro-5-(1,4-dioxan-2-yl)pyrimidine 1622835-32-8 C8H9ClN2O2
2-chloro-6-(methoxy-d3)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-chloro-6-(methoxy-d3)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241867-23-0 C12H14BClD3NO3
2-Cyano-4-(1H-pyridin-2-one)phenylboronic acid pinacol ester 2-Cyano-4-(1H-pyridin-2-one)phenylboronic acid pinacol ester 2223047-51-4 C18H19BN2O3
2-cyclohexyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-cyclohexyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 1402240-80-5 C17H26BNO2
2-cyclohexyl-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-cyclohexyl-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223011-47-8 C17H25BFNO2
2-cyclopropyl-6-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-cyclopropyl-6-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223003-12-9 C19H28BNO3
2-cyclopropyl-6-cyclobutyl-4-hydroxypyrimidine 2-cyclopropyl-6-cyclobutyl-4-hydroxypyrimidine 1412954-05-2 C11H14N2O
2-Ethyl-5-chloropyridine-3-boronic acid pinacol ester 2-Ethyl-5-chloropyridine-3-boronic acid pinacol ester 2223048-87-9 C13H19BClNO2
2-Ethyl-6-methylpyridine-4-boronic acid pinacol ester 2-Ethyl-6-methylpyridine-4-boronic acid pinacol ester 2223043-25-0 C14H22BNO2
2-Fluoro-3-bromo-4-cyclopentylpyridine 2-Fluoro-3-bromo-4-cyclopentylpyridine 1622839-47-7 C10H11BrFN
2-Fluoro-6-(2-chlorophenyl)pyridine 2-Fluoro-6-(2-chlorophenyl)pyridine 1563528-72-2 C11H7ClFN
2-Fluoro-6-(3-chlorophenyl)pyridine 2-Fluoro-6-(3-chlorophenyl)pyridine 1563530-38-0 C11H7ClFN
2-Fluoro-6-(3-furyl)pyridine-3-boronic acid pinacol ester 2-Fluoro-6-(3-furyl)pyridine-3-boronic acid pinacol ester 2223012-48-2 C15H17BFNO3
2-Fluoro-6-(piperidin-4-yl)pyridine 2-Fluoro-6-(piperidin-4-yl)pyridine 1138217-83-0 C10H13FN2
2-Hydroxy-3-(2-methyl-4-fluorophenyl)pyridine 2-Hydroxy-3-(2-methyl-4-fluorophenyl)pyridine 1417518-64-9 C12H10FNO
2-Hydroxy-3-(3,5-difluorophenyl)pyridine 2-Hydroxy-3-(3,5-difluorophenyl)pyridine 1261995-88-3 C11H7F2NO
2-Hydroxy-3-(3-trifluoromethylphenyl)pyridine 2-Hydroxy-3-(3-trifluoromethylphenyl)pyridine 108281-81-8 C12H8F3NO
2-hydroxy-4-(1H-3-methylpyrozol-1-yl)-6-cyclopropylpyrimidine 2-hydroxy-4-(1H-3-methylpyrozol-1-yl)-6-cyclopropylpyrimidine 1412953-90-2 C11H12N4O
2-Hydroxy-4-(1H-pyridin-2-one)-6-methylpyrimidine 2-Hydroxy-4-(1H-pyridin-2-one)-6-methylpyrimidine 1412953-53-7 C10H9N3O2
2-hydroxy-4-(1H-pyrrol-1-yl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(1H-pyrrol-1-yl)-6-(tert-butyl)pyrimidine 1412957-34-6 C12H15N3O
2-Hydroxy-4-(2-furyl)-6-methylpyrimidine 2-Hydroxy-4-(2-furyl)-6-methylpyrimidine 1412960-34-9 C9H8N2O2
2-hydroxy-4-(2-methylpiperidin-1-yl)-6-cyclopropylpyrimidine 2-hydroxy-4-(2-methylpiperidin-1-yl)-6-cyclopropylpyrimidine 1412957-21-1 C13H19N3O
2-Hydroxy-4-(3,5-difluorophenyl)pyrimidine 2-Hydroxy-4-(3,5-difluorophenyl)pyrimidine 1159817-14-7 C10H6F2N2O
2-Hydroxy-4-(3-fluorophenyl)pyrimidine 2-Hydroxy-4-(3-fluorophenyl)pyrimidine 85979-54-0 C10H7FN2O
2-Hydroxy-4-(3-trifluoromethylphenyl)pyrimidine 2-Hydroxy-4-(3-trifluoromethylphenyl)pyrimidine 1159817-30-7 C11H7F3N2O
2-Hydroxy-4-(4-fluoro-2-methylphenyl)pyrimidine 2-Hydroxy-4-(4-fluoro-2-methylphenyl)pyrimidine 1159815-66-3 C11H9FN2O
2-hydroxy-4-(cyclopropyl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(cyclopropyl)-6-(tert-butyl)pyrimidine 1412954-04-1 C11H16N2O
2-Hydroxy-4-(pyridin-2-yl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(pyridin-2-yl)-6-(iso-propyl)pyrimidine 1412961-11-5 C12H13N3O
2-hydroxy-4-(pyridin-3-yl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(pyridin-3-yl)-6-(tert-butyl)pyrimidine 1412954-53-0 C13H15N3O
2-Hydroxy-4-(tert-butoxy)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(tert-butoxy)-6-(iso-propyl)pyrimidine 1412960-10-1 C11H18N2O2
2-hydroxy-4,6-dicyclopropylpyrimidine 2-hydroxy-4,6-dicyclopropylpyrimidine 1412961-28-4 C10H12N2O
2-Hydroxy-4-morpholino-6-methylpyrimidine 2-Hydroxy-4-morpholino-6-methylpyrimidine 62968-24-5 C9H13N3O2
2-Hydroxy-6-trifluoromethylpyridine-4-boronic acid pinacol ester 2-Hydroxy-6-trifluoromethylpyridine-4-boronic acid pinacol ester 2223051-19-0 C12H15BF3NO3
2-Methyl-3-bromopyridine-4-boronic acid pinacol ester 2-Methyl-3-bromopyridine-4-boronic acid pinacol ester 1402172-60-4 C12H17BBrNO2
2-Methyl-6-(iso-propyl)pyridine-4-boronic acid pinacol ester 2-Methyl-6-(iso-propyl)pyridine-4-boronic acid pinacol ester 2223044-48-0 C15H24BNO2
2-methyl-6-(tetrahydrofuran-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-methyl-6-(tetrahydrofuran-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2222997-28-4 C16H24BNO3
3-(3-Furyl)pyridine-2-boronic acid pinacol ester 3-(3-Furyl)pyridine-2-boronic acid pinacol ester 2223013-00-9 C15H18BNO3
3-(4-Fluorophenyl)pyridine-2-boronic acid pinacol ester 3-(4-Fluorophenyl)pyridine-2-boronic acid pinacol ester 2223052-04-6 C17H19BFNO2
3-(6-Bromopyridin-2-yl)phenylboronic acid pinacol ester 3-(6-Bromopyridin-2-yl)phenylboronic acid pinacol ester 2223034-81-7 C17H19BBrNO2
3-(6-Fluoropyridin-2-yl)phenylboronic acid pinacol ester 3-(6-Fluoropyridin-2-yl)phenylboronic acid pinacol ester 2223011-68-3 C17H19BFNO2
3-(Cyclohexyl)pyridine-4-boronic acid pinacol ester 3-(Cyclohexyl)pyridine-4-boronic acid pinacol ester 1402240-83-8 C17H26BNO2
3-(Pyridin-2-yl)-5-methylphenylboronic acid pinacol ester 3-(Pyridin-2-yl)-5-methylphenylboronic acid pinacol ester 2223035-71-8 C18H22BNO2
3-(tetrahydro-2H-pyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(tetrahydro-2H-pyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223053-29-8 C16H24BNO3
3-[5-(Methoxycarbonyl)pyridin-2-yl]phenylboronic acid pinacol ester 3-[5-(Methoxycarbonyl)pyridin-2-yl]phenylboronic acid pinacol ester 2223012-93-7 C19H22BNO4
3-Amino-6-(3-furyl)pyridazine 3-Amino-6-(3-furyl)pyridazine 1159821-50-7 C8H7N3O
3-Amino-6-(3-trifluoromethylphenyl)pyridazine 3-Amino-6-(3-trifluoromethylphenyl)pyridazine 102627-28-1 C11H8F3N3
3-Amino-6-(iso-propenyl)pyridazine 3-Amino-6-(iso-propenyl)pyridazine 1314356-34-7 C7H9N3
3-Amino-6-(n-propyl)pyridazine 3-Amino-6-(n-propyl)pyridazine 1057672-69-1 C7H11N3
3-Bromo-1-ethyl-1H-pyrrole 3-Bromo-1-ethyl-1H-pyrrole 1138323-27-9 C6H8BrN
3-Bromo-2-(iso-propyl)pyridine-4-boronic acid pinacol ester 3-Bromo-2-(iso-propyl)pyridine-4-boronic acid pinacol ester 2223038-10-4 C14H21BBrNO2
3-Bromo-2-fluoro-6-(N-Boc-pyrrolidin-3-yl)pyridine 3-Bromo-2-fluoro-6-(N-Boc-pyrrolidin-3-yl)pyridine 1622836-21-8 C14H18BrFN2O2
3-Bromo-2-fluoro-6-(oxolan-2-yl)pyridine 3-Bromo-2-fluoro-6-(oxolan-2-yl)pyridine 1622834-13-2 C9H9BrFNO
3-Bromo-4-(2-thienyl)-2-chloropyridine 3-Bromo-4-(2-thienyl)-2-chloropyridine 1622843-15-5 C9H5BrClNS
3-Bromo-4-(thiazol-2-yl)-2-chloropyridine 3-Bromo-4-(thiazol-2-yl)-2-chloropyridine 1622839-87-5 C8H4BrClN2S
3-Bromo-4-chloro-6-(n-propyl)pyridine 3-Bromo-4-chloro-6-(n-propyl)pyridine 1353853-79-8 C8H9BrClN
3-Bromo-6-(2-methylpyrimidyl-5-yl)pyridazine 3-Bromo-6-(2-methylpyrimidyl-5-yl)pyridazine 1215072-70-0 C9H7BrN4
3-Bromo-6-(3,5-difluorophenyl)pyridazine 3-Bromo-6-(3,5-difluorophenyl)pyridazine 1215073-38-3 C10H5BrF2N2
3-Bromo-6-(4-tolyl)pyridazine 3-Bromo-6-(4-tolyl)pyridazine 1086383-90-5 C11H9BrN2
3-Bromo-6-(cyclobutoxy)pyridazine 3-Bromo-6-(cyclobutoxy)pyridazine 1086383-99-4 C8H9BrN2O
3-Bromo-6-(n-propyl)pyridazine 3-Bromo-6-(n-propyl)pyridazine 93216-56-9 C7H9BrN2
3-Bromo-6-methylpyridine-4-boronic acid pinacol ester 3-Bromo-6-methylpyridine-4-boronic acid pinacol ester 2223044-76-4 C12H17BBrNO2
3-Hydroxy-6-(5-aminopyridyl-3-yl)pyridazine 3-Hydroxy-6-(5-aminopyridyl-3-yl)pyridazine 1215073-75-8 C9H8N4O
3-Methyl-2-(tert-butyl)pyridine-4-boronic acid pinacol ester 3-Methyl-2-(tert-butyl)pyridine-4-boronic acid pinacol ester 2223051-37-2 C16H26BNO2
3-Methyl-4-(1H-pyridin-2-one)phenylboronic acid pinacol ester 3-Methyl-4-(1H-pyridin-2-one)phenylboronic acid pinacol ester 2223054-96-2 C18H22BNO3
4-(1,4-dioxan-2-yl)pyrimidin-2-amine 4-(1,4-dioxan-2-yl)pyrimidin-2-amine 1622834-26-7 C8H11N3O2
4-(2-Tolyl)-1,3,5-triazin-2-amine 4-(2-Tolyl)-1,3,5-triazin-2-amine 1342575-79-4 C10H10N4
4-(3,5-Difluorophenyl)-1,3,5-triazin-2-amine 4-(3,5-Difluorophenyl)-1,3,5-triazin-2-amine 1343387-72-3 C9H6F2N4
4-(3-Methoxyphenyl)-1,3,5-triazin-2-amine 4-(3-Methoxyphenyl)-1,3,5-triazin-2-amine 1343859-46-0 C10H10N4O
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(p-tolyl)thiazole 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(p-tolyl)thiazole 1402173-87-8 C16H20BNO2S
4-(5-Pyrimidyl)thiazole-5-boronic acid pinacol ester 4-(5-Pyrimidyl)thiazole-5-boronic acid pinacol ester 2223042-32-6 C13H16BN3O2S
4-(6-Bromo-2-pyridinyl)-4-piperidinol 4-(6-Bromo-2-pyridinyl)-4-piperidinol 1622841-03-5 C10H13BrN2O
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