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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
3-Amino-6-(4-methyl-1H-pyrazol-1-yl)pyridazine 3-Amino-6-(4-methyl-1H-pyrazol-1-yl)pyridazine 1314356-35-8 C8H9N5
3-Amino-6-(n-propyl)pyridine-4-boronic acid pinacol ester 3-Amino-6-(n-propyl)pyridine-4-boronic acid pinacol ester 2223038-48-8 C14H23BN2O2
3-Bromo-2-(n-propyl)pyridine-4-boronic acid pinacol ester 3-Bromo-2-(n-propyl)pyridine-4-boronic acid pinacol ester 2223044-95-7 C14H21BBrNO2
3-Bromo-2-fluoro-6-(oxolan-3-yl)pyridine 3-Bromo-2-fluoro-6-(oxolan-3-yl)pyridine 1622835-29-3 C9H9BrFNO
3-Bromo-4-(2-thienyl)-2-pyridinecarbonitrile 3-Bromo-4-(2-thienyl)-2-pyridinecarbonitrile 1622843-07-5 C10H5BrN2S
3-Bromo-4-(iso-butyl)-2-chloropyridine 3-Bromo-4-(iso-butyl)-2-chloropyridine 1622839-33-1 C9H11BrClN
3-Bromo-4-(thiazol-2-yl)-2-pyridinecarbonitrile 3-Bromo-4-(thiazol-2-yl)-2-pyridinecarbonitrile 1622843-11-1 C9H4BrN3S
3-Bromo-4-chloro-6-cyclobutylpyridine 3-Bromo-4-chloro-6-cyclobutylpyridine 1353856-71-9 C9H9BrClN
3-Bromo-4-ethyl-2-pyridinecarbonitrile 3-Bromo-4-ethyl-2-pyridinecarbonitrile 64303-90-8 C8H7BrN2
3-Bromo-6-(2-thienyl)pyridazine 3-Bromo-6-(2-thienyl)pyridazine 172507-39-0 C8H5BrN2S
3-Bromo-6-(3-aminophenyl)pyridazine 3-Bromo-6-(3-aminophenyl)pyridazine 1215071-33-2 C10H8BrN3
3-Bromo-6-(4-trifluoromethylphenyl)pyridazine 3-Bromo-6-(4-trifluoromethylphenyl)pyridazine 1215072-74-4 C11H6BrF3N2
3-Bromo-6-(cyclobutyl)pyridazine 3-Bromo-6-(cyclobutyl)pyridazine 1086384-05-5 C8H9BrN2
3-Bromo-6-(pyrimidyl-5-yl)pyridazine 3-Bromo-6-(pyrimidyl-5-yl)pyridazine 1215072-11-9 C8H5BrN4
3-Cyano-6-methylpyridine-4-boronic acid pinacol ester 3-Cyano-6-methylpyridine-4-boronic acid pinacol ester 2223027-55-0 C13H17BN2O2
3-Hydroxy-6-(2-aminopyrimidyl-5-yl)pyridazine 3-Hydroxy-6-(2-aminopyrimidyl-5-yl)pyridazine 1215073-51-0 C8H7N5O
3-Hydroxy-6-(5-fluoropyridyl-2-yl)pyridazine 3-Hydroxy-6-(5-fluoropyridyl-2-yl)pyridazine 1215071-64-9 C9H6FN3O
4-(1,4-dioxan-2-yl)pyrimidin-2-ol 4-(1,4-dioxan-2-yl)pyrimidin-2-ol 2222934-19-0 C8H10N2O3
4-(3-Tolyl)-1,3,5-triazin-2-amine 4-(3-Tolyl)-1,3,5-triazin-2-amine 1343249-85-3 C10H10N4
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(thiophen-2-yl)thiazole 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(thiophen-2-yl)thiazole 1402166-57-7 C13H16BNO2S2
4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-yl)pyridine 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-yl)pyridine 2223048-43-7 C15H18BNO3
4-(Cyclopentyl)-1,3,5-triazin-2-amine 4-(Cyclopentyl)-1,3,5-triazin-2-amine 1343643-72-0 C8H12N4
4-(n-Propyl)-1,3,5-triazin-2-amine 4-(n-Propyl)-1,3,5-triazin-2-amine 1417518-55-8 C6H10N4
4,4,5,5-tetramethyl-2-(4-(tetrahydrofuran-3-yl)furan-2-yl)-1,3,2-dioxaborolane 4,4,5,5-tetramethyl-2-(4-(tetrahydrofuran-3-yl)furan-2-yl)-1,3,2-dioxaborolane 2223002-73-9 C14H21BO4
4,4'-Di(tert-butyl)-2,2'-bithiazole 4,4'-Di(tert-butyl)-2,2'-bithiazole 287977-89-3 C14H20N2S2
4,6-Dichloro-2-(4-trifluoromethylphenyl)pyrimidine 4,6-Dichloro-2-(4-trifluoromethylphenyl)pyrimidine 180607-14-1 C11H5Cl2F3N2
4-Amino-2-(1,4-dioxan-2-yl)thiazole 4-Amino-2-(1,4-dioxan-2-yl)thiazole 1622835-15-7 C7H10N2O2S
4-Amino-2-(3-methoxyphenyl)pyrimidine 4-Amino-2-(3-methoxyphenyl)pyrimidine 1215071-67-2 C11H11N3O
4-Amino-2-(3-trifluoromethylphenyl)pyrimidine 4-Amino-2-(3-trifluoromethylphenyl)pyrimidine 125927-04-0 C11H8F3N3
4-Amino-2-(iso-propyl)-6-(1H-4-methylimidazol-1-yl)-pyrimidine 4-Amino-2-(iso-propyl)-6-(1H-4-methylimidazol-1-yl)-pyrimidine 1412955-41-9 C11H15N5
4-Amino-2-(iso-propyl)-6-(4-tetrahydropyranyl)pyrimidine 4-Amino-2-(iso-propyl)-6-(4-tetrahydropyranyl)pyrimidine 1412954-18-7 C12H19N3O
4-Amino-2-(iso-propyl)-6-(pyrimidin-5-yl)pyrimidine 4-Amino-2-(iso-propyl)-6-(pyrimidin-5-yl)pyrimidine 1412955-91-9 C11H13N5
4-Amino-2-(iso-propyl)pyrimidine-5-boronic acid pinacol ester 4-Amino-2-(iso-propyl)pyrimidine-5-boronic acid pinacol ester 2223041-67-4 C13H22BN3O2
4-Amino-2-cyclopropyl-6-(4-chlorophenyl)pyrimidine 4-Amino-2-cyclopropyl-6-(4-chlorophenyl)pyrimidine 1292401-77-4 C13H12ClN3
4-amino-2-cyclopropyl-6-cyclohexylpyrimidine 4-amino-2-cyclopropyl-6-cyclohexylpyrimidine 1412954-47-2 C13H19N3
4-Amino-2-fluoro-6-(piperidin-3-yl)pyridine 4-Amino-2-fluoro-6-(piperidin-3-yl)pyridine 1622835-52-2 C10H14FN3
4-amino-2-methyl-6-(3-thienyl)pyrimidine 4-amino-2-methyl-6-(3-thienyl)pyrimidine 1412957-83-5 C9H9N3S
4-Amino-5-bromopyridine-3-boronic acid pinacol ester 4-Amino-5-bromopyridine-3-boronic acid pinacol ester 2223053-96-9 C11H16BBrN2O2
4-Amino-6-(n-propyl)pyridine-3-boronic acid pinacol ester 4-Amino-6-(n-propyl)pyridine-3-boronic acid pinacol ester 2223047-12-7 C14H23BN2O2
4-Bromo-2-(iso-propyl)-6-(1H-4-methylimidazol-1-yl)-pyrimidine 4-Bromo-2-(iso-propyl)-6-(1H-4-methylimidazol-1-yl)-pyrimidine 1412956-80-9 C11H13BrN4
4-Bromo-2-(iso-propyl)-6-(1H-pyrrol-1-yl)pyrimidine 4-Bromo-2-(iso-propyl)-6-(1H-pyrrol-1-yl)pyrimidine 1412954-02-9 C11H12BrN3
4-bromo-2-(iso-propyl)-6-(pyridin-4-yl)-pyrimidine 4-bromo-2-(iso-propyl)-6-(pyridin-4-yl)-pyrimidine 1412957-91-5 C12H12BrN3
4-Bromo-2-(methoxycarbonyl)-6-(1-methylethyl)pyridine 4-Bromo-2-(methoxycarbonyl)-6-(1-methylethyl)pyridine 1643564-08-2 C10H12BrNO2
4-Bromo-2,2'-bithiazole 4-Bromo-2,2'-bithiazole 1622843-77-9 C6H3BrN2S2
4-Bromo-2-cyclobutyl-5-fluoropyridine 4-Bromo-2-cyclobutyl-5-fluoropyridine 1643564-24-2 C9H9BrFN
4-Bromo-2-cyclopropyl-6-(1H-pyridin-2-one)pyrimidine 4-Bromo-2-cyclopropyl-6-(1H-pyridin-2-one)pyrimidine 1412954-64-3 C12H10BrN3O
4-Bromo-2-cyclopropyl-6-(3-pyridyl)pyrimidine 4-Bromo-2-cyclopropyl-6-(3-pyridyl)pyrimidine 1412958-30-5 C12H10BrN3
4-Bromo-2-cyclopropyl-6-(4-methylpiperidin-1-yl)pyrimidine 4-Bromo-2-cyclopropyl-6-(4-methylpiperidin-1-yl)pyrimidine 1412954-88-1 C13H18BrN3
4-bromo-2-cyclopropyl-6-cyclopentylpyrimidine 4-bromo-2-cyclopropyl-6-cyclopentylpyrimidine 1412961-97-7 C12H15BrN2
4-bromo-2-methyl-6-(2-methylpiperidin-1-yl)pyrimidine 4-bromo-2-methyl-6-(2-methylpiperidin-1-yl)pyrimidine 1412961-84-2 C11H16BrN3
4-Bromo-2-methyl-6-(piperidin-3-yl)pyridine 4-Bromo-2-methyl-6-(piperidin-3-yl)pyridine 1622834-28-9 C11H15BrN2
4-Bromo-3-(iso-propyl)pyridine 4-Bromo-3-(iso-propyl)pyridine 10168-01-1 C8H10BrN
4-Bromo-3-cyclohextylpyridine 4-Bromo-3-cyclohextylpyridine 1314356-44-9 C11H14BrN
4-Bromo-4'-methyl-2,2'-bithiazole 4-Bromo-4'-methyl-2,2'-bithiazole 1622842-85-6 C7H5BrN2S2
4-Bromo-5-methyl-2-(tetrahydrofuran-3-yl)pyridine 4-Bromo-5-methyl-2-(tetrahydrofuran-3-yl)pyridine 1381937-93-4 C10H12BrNO
4-Bromo-6-(2-fluorophenyl)-2-(iso-propyl)pyrimidine 4-Bromo-6-(2-fluorophenyl)-2-(iso-propyl)pyrimidine 1412956-05-8 C13H12BrFN2
4-Bromo-6-(iso-propyl)pyridine-2-boronic acid pinacol ester 4-Bromo-6-(iso-propyl)pyridine-2-boronic acid pinacol ester 1402233-23-1 C14H21BBrNO2
4-bromo-6-cyclobutyl-2-methylpyrimidine 4-bromo-6-cyclobutyl-2-methylpyrimidine 1412954-79-0 C9H11BrN2
4-Chloro-2-(1H-pyrazol-1-yl)pyrimidine 4-Chloro-2-(1H-pyrazol-1-yl)pyrimidine 1017795-16-2 C7H5ClN4
4-Chloro-2-(3,5-difluorophenyl)pyrimidine 4-Chloro-2-(3,5-difluorophenyl)pyrimidine 1215072-63-1 C10H5ClF2N2
4-Chloro-2-(4-tert-butylphenyl)pyrimidine 4-Chloro-2-(4-tert-butylphenyl)pyrimidine 1155599-70-4 C14H15ClN2
4-chloro-2-(iso-propyl)-6-(1H-pyridin-2-one)-pyrimidine 4-chloro-2-(iso-propyl)-6-(1H-pyridin-2-one)-pyrimidine 1412953-89-9 C12H12ClN3O
4-chloro-2-(iso-propyl)-6-(2-thienyl)pyrimidine 4-chloro-2-(iso-propyl)-6-(2-thienyl)pyrimidine 1412957-96-0 C11H11ClN2S
4-chloro-2-(iso-propyl)-6-(tert-butoxy)pyrimidine 4-chloro-2-(iso-propyl)-6-(tert-butoxy)pyrimidine 1412952-96-5 C11H17ClN2O
4-Chloro-2-(n-propoxy)pyrimidine 4-Chloro-2-(n-propoxy)pyrimidine 1563533-48-1 C7H9ClN2O
4-Chloro-2-cyclopropyl-6-(3-thienyl)pyrimidine 4-Chloro-2-cyclopropyl-6-(3-thienyl)pyrimidine 1412957-62-0 C11H9ClN2S
4-chloro-2-cyclopropyl-6-cyclopentylpyrimidine 4-chloro-2-cyclopropyl-6-cyclopentylpyrimidine 1412957-16-4 C12H15ClN2
4-chloro-2-methyl-6-(1H-4-methylimidazol-1-yl)pyrimidine 4-chloro-2-methyl-6-(1H-4-methylimidazol-1-yl)pyrimidine 1289003-52-6 C9H9ClN4
4-Chloro-5-(n-propyl)pyridine-2-boronic acid pinacol ester 4-Chloro-5-(n-propyl)pyridine-2-boronic acid pinacol ester 2223037-51-0 C14H21BClNO2
4-chloro-6-(2-chlorophenyl)-2-(iso-propyl)pyrimidine 4-chloro-6-(2-chlorophenyl)-2-(iso-propyl)pyrimidine 1412955-21-5 C13H12Cl2N2
4-chloro-6-(3-furyl)-2-methylpyrimidine 4-chloro-6-(3-furyl)-2-methylpyrimidine 569658-33-9 C9H7ClN2O
4-chloro-6-cyclopentyl-2-(propan-2-yl)pyrimidine 4-chloro-6-cyclopentyl-2-(propan-2-yl)pyrimidine 1412960-20-3 C12H17ClN2
4-CHLORO-N-ETHYL-N-METHYL-4-PYRIMIDINAMINE 4-CHLORO-N-ETHYL-N-METHYL-4-PYRIMIDINAMINE 771556-83-3 C7H10ClN3
4-Fluoro-2-(2-methylimidazol-1-yl)pyridine-5-boronic acid pinacol ester 4-Fluoro-2-(2-methylimidazol-1-yl)pyridine-5-boronic acid pinacol ester 2223049-13-4 C15H19BFN3O2
4-Fluoro-2-(2-trifluoromethylphenyl)pyridine 4-Fluoro-2-(2-trifluoromethylphenyl)pyridine 1261818-71-6 C12H7F4N
4-Fluoro-2-(4-aminophenyl)pyridine 4-Fluoro-2-(4-aminophenyl)pyridine 1563528-65-3 C11H9FN2
4-Fluoro-2-(4-methoxyphenyl)pyridine 4-Fluoro-2-(4-methoxyphenyl)pyridine 1563529-87-2 C12H10FNO
4-Fluoro-2-(cyclohexyloxy)pyridine-5-boronic acid pinacol ester 4-Fluoro-2-(cyclohexyloxy)pyridine-5-boronic acid pinacol ester 2223041-18-5 C17H25BFNO3
4-Fluoro-2-(pyrimidin-2-yl)pyridine 4-Fluoro-2-(pyrimidin-2-yl)pyridine 1563530-06-2 C9H6FN3
4-Fluoro-2-(sec-butyl)pyridine 4-Fluoro-2-(sec-butyl)pyridine 1563528-79-9 C9H12FN
4-fluoro-2-isobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-fluoro-2-isobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223033-45-0 C15H23BFNO2
4-Hydroxy-2-(2-methoxyphenyl)pyrimidine 4-Hydroxy-2-(2-methoxyphenyl)pyrimidine 1156239-99-4 C11H10N2O2
4-Hydroxy-2-(4-fluorophenyl)pyrimidine 4-Hydroxy-2-(4-fluorophenyl)pyrimidine 76128-79-5 C10H7FN2O
4-Hydroxy-2-(iso-propyl)-6-(2-thienyl)pyrimidine 4-Hydroxy-2-(iso-propyl)-6-(2-thienyl)pyrimidine 1412958-01-0 C11H12N2OS
4-Hydroxy-2-(iso-propyl)-6-(3-thienyl)pyrimidine 4-Hydroxy-2-(iso-propyl)-6-(3-thienyl)pyrimidine 1412953-85-5 C11H12N2OS
4-Hydroxy-2-cyclopropyl-6-(3-methyl-1H-pyrazol-1-yl)pyrimidine 4-Hydroxy-2-cyclopropyl-6-(3-methyl-1H-pyrazol-1-yl)pyrimidine 1412956-36-5 C11H12N4O
4-Hydroxy-2-cyclopropyl-6-(4-methylpiperidin-1-yl)pyrimidine 4-Hydroxy-2-cyclopropyl-6-(4-methylpiperidin-1-yl)pyrimidine 1412956-15-0 C13H19N3O
4-hydroxy-2-methyl-6-(1H-pyrozol-1-yl)pyrimidine 4-hydroxy-2-methyl-6-(1H-pyrozol-1-yl)pyrimidine 1412957-60-8 C8H8N4O
4-hydroxy-6-cyclopentyl-2-methylpyrimidine 4-hydroxy-6-cyclopentyl-2-methylpyrimidine 1412959-83-1 C10H14N2O
4-nitropyridine-2,3,5,6-d4 4-nitropyridine-2,3,5,6-d4 1185310-51-3 C5D4N2O2
5-(1H-Pyridin-2-one)pyridine-2-boronic acid pinacol ester 5-(1H-Pyridin-2-one)pyridine-2-boronic acid pinacol ester 1402172-65-9 C16H19BN2O3
5-(2-Aminopropan-2-yl)pyridine-3-boronic acid pinacol ester 5-(2-Aminopropan-2-yl)pyridine-3-boronic acid pinacol ester 2223011-79-6 C14H23BN2O2
5-(2-Chlorophenyl)pyridine-2-boronic acid pinacol ester 5-(2-Chlorophenyl)pyridine-2-boronic acid pinacol ester 2223051-26-9 C17H19BClNO2
5-(2-Trifluoromethylphenyl)pyridine-3-boronic acid pinacol ester 5-(2-Trifluoromethylphenyl)pyridine-3-boronic acid pinacol ester 1402233-70-8 C18H19BF3NO2
5-(3, 4-Difluorophenyl)pyridine-3-boronic acid pinacol ester 5-(3, 4-Difluorophenyl)pyridine-3-boronic acid pinacol ester 1402227-56-8 C17H18BF2NO2
5-(3-Chlorophenyl)pyridine-2-boronic acid pinacol ester 5-(3-Chlorophenyl)pyridine-2-boronic acid pinacol ester 2223044-07-1 C17H19BClNO2
5-(4-Ethylphenyl)pyridine-3-boronic acid pinacol ester 5-(4-Ethylphenyl)pyridine-3-boronic acid pinacol ester 1402174-67-7 C19H24BNO2
5-(5-Methyl-2-pyridyl)pyrazine-2-boronic acid pinacol ester 5-(5-Methyl-2-pyridyl)pyrazine-2-boronic acid pinacol ester 1402172-50-2 C16H20BN3O2
5-(6-Amino-3-pyridyl)pyridine-2-boronic acid pinacol ester 5-(6-Amino-3-pyridyl)pyridine-2-boronic acid pinacol ester 1402172-52-4 C16H20BN3O2
5-(iso-Butyl)-6-methoxypyridine-3-boronic acid pinacol ester 5-(iso-Butyl)-6-methoxypyridine-3-boronic acid pinacol ester 2223042-06-4 C16H26BNO3
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