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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
4-Amino-2-(1H-pyrrol-1-yl)thiazole 4-Amino-2-(1H-pyrrol-1-yl)thiazole 1314356-49-4 C7H7N3S
4-Amino-2-(4-methyl-1H-pyrazol-1-yl)thiazole 4-Amino-2-(4-methyl-1H-pyrazol-1-yl)thiazole 1314355-49-1 C7H8N4S
4-Amino-2-(cyclobutyll)pyrimidine-5-boronic acid pinacol ester 4-Amino-2-(cyclobutyll)pyrimidine-5-boronic acid pinacol ester 2223031-18-1 C14H22BN3O2
4-Amino-2-(iso-propyl)-6-(1H-pyrozol-1-yl)pyrimidine 4-Amino-2-(iso-propyl)-6-(1H-pyrozol-1-yl)pyrimidine 1412961-95-5 C10H13N5
4-Amino-2-(iso-propyl)-6-(2-tolyl)pyrimidine 4-Amino-2-(iso-propyl)-6-(2-tolyl)pyrimidine 1306432-80-3 C14H17N3
4-Amino-2-(pyridin-4-yl)pyrimidine-5-boronic acid pinacol ester 4-Amino-2-(pyridin-4-yl)pyrimidine-5-boronic acid pinacol ester 2223031-74-9 C15H19BN4O2
4-Amino-2-cyclopropyl-6-(3-thienyl)pyrimidine 4-Amino-2-cyclopropyl-6-(3-thienyl)pyrimidine 1412959-56-8 C11H11N3S
4-Amino-2-cyclopropyl-6-(4-tetrahydropyranyl)pyrimidine 4-Amino-2-cyclopropyl-6-(4-tetrahydropyranyl)pyrimidine 1412958-21-4 C12H17N3O
4-Amino-2-ethylpyrimidine-5-boronic acid pinacol ester 4-Amino-2-ethylpyrimidine-5-boronic acid pinacol ester 2223048-17-5 C12H20BN3O2
4-amino-2-methyl-6-(1H-2-methylimidazol-1-yl)pyrimidine 4-amino-2-methyl-6-(1H-2-methylimidazol-1-yl)pyrimidine 1412955-70-4 C9H11N5
4-Amino-2-methyl-6-(piperidin-4-yl)pyridine 4-Amino-2-methyl-6-(piperidin-4-yl)pyridine 1622841-01-3 C11H17N3
4-Amino-2-trifluoromethyl-6-(piperidin-3-yl)pyridine 4-Amino-2-trifluoromethyl-6-(piperidin-3-yl)pyridine 1622835-50-0 C11H14F3N3
4-Amino-6-(2-fluorophenyl)-2-(iso-propyl)pyrimidine 4-Amino-6-(2-fluorophenyl)-2-(iso-propyl)pyrimidine 1306319-75-4 C13H14FN3
4-Amino-6-(3-hydroxypyrrolidino)pyrimidine 4-Amino-6-(3-hydroxypyrrolidino)pyrimidine 1314356-38-1 C8H12N4O
4-amino-6-cyclopentyl-2-methylpyrimidine 4-amino-6-cyclopentyl-2-methylpyrimidine 1412957-63-1 C10H15N3
4-Bromo-2-(2-aminophenyl)pyrimidine 4-Bromo-2-(2-aminophenyl)pyrimidine 1142195-07-0 C10H8BrN3
4-Bromo-2-(2-methyl-4-fluorophenyl)pyrimidine 4-Bromo-2-(2-methyl-4-fluorophenyl)pyrimidine 1215073-46-3 C11H8BrFN2
4-Bromo-2-(cyclobutylamino)thiazole 4-Bromo-2-(cyclobutylamino)thiazole 1159816-46-2 C7H9BrN2S
4-Bromo-2-(iso-butyl)pyrimidine 4-Bromo-2-(iso-butyl)pyrimidine 1142195-71-8 C8H11BrN2
4-Bromo-2-(iso-propyl)-6-(2-tolyl)pyrimidine 4-Bromo-2-(iso-propyl)-6-(2-tolyl)pyrimidine 1412956-24-1 C14H15BrN2
4-Bromo-2-(N-Boc-pyrrolidin-3-yl)thiazole 4-Bromo-2-(N-Boc-pyrrolidin-3-yl)thiazole 1622834-50-7 C12H17BrN2O2S
4-Bromo-2-(piperidin-3-ol)thiazole 4-Bromo-2-(piperidin-3-ol)thiazole 959239-54-4 C8H11BrN2OS
4-Bromo-2-amino-5-(morpholino)pyridine 4-Bromo-2-amino-5-(morpholino)pyridine 1381942-09-1 C9H12BrN3O
4-Bromo-2-cyclopropyl-6-(2-furyl)pyrimidine 4-Bromo-2-cyclopropyl-6-(2-furyl)pyrimidine 1412959-23-9 C11H9BrN2O
4-Bromo-2-cyclopropyl-6-(2-tolyl)pyrimidine 4-Bromo-2-cyclopropyl-6-(2-tolyl)pyrimidine 1412954-11-0 C14H13BrN2
4-Bromo-2-cyclopropyl-6-(imidazol-1-yl)pyrimidine 4-Bromo-2-cyclopropyl-6-(imidazol-1-yl)pyrimidine 1412958-99-6 C10H9BrN4
4-Bromo-2-cyclopropyl-6-(piperidino)pyrimidine 4-Bromo-2-cyclopropyl-6-(piperidino)pyrimidine 1412959-71-7 C12H16BrN3
4-Bromo-2-fluoro-6-cyclopropylpyridine 4-Bromo-2-fluoro-6-cyclopropylpyridine 1622841-07-9 C8H7BrFN
4-bromo-2-methyl-6-(1H-4-methylimidazol-1-yl)pyrimidine 4-bromo-2-methyl-6-(1H-4-methylimidazol-1-yl)pyrimidine 1412960-19-0 C9H9BrN4
4-bromo-2-methyl-6-(pyridin-4-yl)pyrimidine 4-bromo-2-methyl-6-(pyridin-4-yl)pyrimidine 1412957-84-6 C10H8BrN3
4-Bromo-3-fluoro-2-(oxan-4-yl)pyridine 4-Bromo-3-fluoro-2-(oxan-4-yl)pyridine 1643537-32-9 C10H11BrFNO
4-Bromo-5-(4-pyridyl)thiazole 4-Bromo-5-(4-pyridyl)thiazole 1417519-66-4 C8H5BrN2S
4-bromo-6-(3-chlorophenyl)-2-methylpyrimidine 4-bromo-6-(3-chlorophenyl)-2-methylpyrimidine 1412955-33-9 C11H8BrClN2
4-bromo-6-cyclobutyl-2-(propan-2-yl)pyrimidine 4-bromo-6-cyclobutyl-2-(propan-2-yl)pyrimidine 1412958-86-1 C11H15BrN2
4-bromo-6-cyclopentyl-2-methylpyrimidine 4-bromo-6-cyclopentyl-2-methylpyrimidine 1412956-03-6 C10H13BrN2
4-Chloro-2-(3-trifluoromethylphenyl)pyrimidine 4-Chloro-2-(3-trifluoromethylphenyl)pyrimidine 125904-01-0 C11H6ClF3N2
4-Chloro-2-(iso-propoxy)pyrimidine 4-Chloro-2-(iso-propoxy)pyrimidine 1563529-93-0 C7H9ClN2O
4-chloro-2-(iso-propyl)-6-(3-methylpiperidin-1-yl)pyrimidine 4-chloro-2-(iso-propyl)-6-(3-methylpiperidin-1-yl)pyrimidine 1412956-61-6 C13H20ClN3
4-chloro-2-(iso-propyl)-6-(piperidin-1-yl)-pyrimidine 4-chloro-2-(iso-propyl)-6-(piperidin-1-yl)-pyrimidine 68210-31-1 C12H18ClN3
4-Chloro-2-cyclopropyl-6-(1H-pyridin-2-one)pyrimidine 4-Chloro-2-cyclopropyl-6-(1H-pyridin-2-one)pyrimidine 1412960-85-0 C12H10ClN3O
4-Chloro-2-cyclopropyl-6-(4-methylpiperidin-1-yl)pyrimidine 4-Chloro-2-cyclopropyl-6-(4-methylpiperidin-1-yl)pyrimidine 1412958-37-2 C13H18ClN3
4-Chloro-2-cyclopropyl-6-(morpholino)pyrimidine 4-Chloro-2-cyclopropyl-6-(morpholino)pyrimidine 1412954-81-4 C11H14ClN3O
4-chloro-2-methyl-6-(1H-pyrrol-1-yl)pyrimidine 4-chloro-2-methyl-6-(1H-pyrrol-1-yl)pyrimidine 1412961-88-6 C9H8ClN3
4-chloro-2-methyl-6-(4-methylpiperidin-1-yl)pyrimidine 4-chloro-2-methyl-6-(4-methylpiperidin-1-yl)pyrimidine 1249243-11-5 C11H16ClN3
4-chloro-5-isopropyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-chloro-5-isopropyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223013-03-2 C14H21BClNO2
4-CHLORO-5-METHYLPYRIDINE-3-BORONIC ACID PINACOL ESTER 4-CHLORO-5-METHYLPYRIDINE-3-BORONIC ACID PINACOL ESTER 2223012-31-3 C12H17BClNO2
4-Chloro-6-bromo-2-ethylpyrimidine 4-Chloro-6-bromo-2-ethylpyrimidine 1353853-53-8 C6H6BrClN2
4-Fluoro-2-(2-chlorophenyl)pyridine 4-Fluoro-2-(2-chlorophenyl)pyridine 1563530-57-3 C11H7ClFN
4-Fluoro-2-(3-cyanophenyl)pyridine 4-Fluoro-2-(3-cyanophenyl)pyridine 1563528-75-5 C12H7FN2
4-Fluoro-2-(3-methyl-1H-pyrazol-1-yl)pyridine-5-boronic acid pinacol ester 4-Fluoro-2-(3-methyl-1H-pyrazol-1-yl)pyridine-5-boronic acid pinacol ester 2223035-08-1 C15H19BFN3O2
4-Fluoro-2-(4-methylimidazol-1-yl)pyridine-5-boronic acid pinacol ester 4-Fluoro-2-(4-methylimidazol-1-yl)pyridine-5-boronic acid pinacol ester 2223041-20-9 C15H19BFN3O2
4-Fluoro-2-(imidazol-1-yl)pyridine-5-boronic acid pinacol ester 4-Fluoro-2-(imidazol-1-yl)pyridine-5-boronic acid pinacol ester 2223045-57-4 C14H17BFN3O2
4-Fluoro-2-(n-propyl)pyridine-5-boronic acid pinacol ester 4-Fluoro-2-(n-propyl)pyridine-5-boronic acid pinacol ester 2223048-50-6 C14H21BFNO2
4-Fluoro-2-(piperidin-4-yl)pyridine 4-Fluoro-2-(piperidin-4-yl)pyridine 1563530-89-1 C10H13FN2
4-Fluoro-2-(thiazol-4-yl)pyridine 4-Fluoro-2-(thiazol-4-yl)pyridine 1563530-82-4 C8H5FN2S
4-Hydroxy-2-(iso-propyl)-6-(pyridin-2-yl)-pyrimidine 4-Hydroxy-2-(iso-propyl)-6-(pyridin-2-yl)-pyrimidine 1239786-55-0 C12H13N3O
4-Hydroxy-2-cyclopropyl-6-(4-methylimidazol-1-yl)pyrimidine 4-Hydroxy-2-cyclopropyl-6-(4-methylimidazol-1-yl)pyrimidine 1412958-44-1 C11H12N4O
4-Hydroxy-2-cyclopropyl-6-(morpholino)pyrimidine 4-Hydroxy-2-cyclopropyl-6-(morpholino)pyrimidine 1412962-01-6 C11H15N3O2
4-hydroxy-2-methyl-6-(3-methylpiperidin-1-yl)pyrimidine 4-hydroxy-2-methyl-6-(3-methylpiperidin-1-yl)pyrimidine 1412961-22-8 C11H17N3O
4-Hydroxy-2-methyl-6-(pyrrolidin-1-yl)pyrimidine 4-Hydroxy-2-methyl-6-(pyrrolidin-1-yl)pyrimidine 1412958-68-9 C9H13N3O
4-Methyl-5-(sec-butyl)pyridine-3-boronic acid pinacol ester 4-Methyl-5-(sec-butyl)pyridine-3-boronic acid pinacol ester 2223009-59-2 C16H26BNO2
4-Methyl-6-(iso-propyl)pyridine-3-boronic acid pinacol ester 4-Methyl-6-(iso-propyl)pyridine-3-boronic acid pinacol ester 2223048-42-6 C15H24BNO2
5-(1,4-dioxan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(1,4-dioxan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223003-76-5 C15H22BNO4
5-(1-Pivaloylpiperidin-4-yl)pyridine-3-boronic acid pinacol ester 5-(1-Pivaloylpiperidin-4-yl)pyridine-3-boronic acid pinacol ester 2223054-38-2 C21H33BN2O3
5-(3,4-Difluorophenyl)pyridine-2-boronic acid pinacol ester 5-(3,4-Difluorophenyl)pyridine-2-boronic acid pinacol ester 2223054-19-9 C17H18BF2NO2
5-(4-Aminophenyl)pyridine-2-boronic acid pinacol ester 5-(4-Aminophenyl)pyridine-2-boronic acid pinacol ester 1402172-39-7 C17H21BN2O2
5-(4-Methylpiperidin-1-yl)pyridine-3-boronic acid pinacol ester 5-(4-Methylpiperidin-1-yl)pyridine-3-boronic acid pinacol ester 1402174-02-0 C17H27BN2O2
5-(4-Tolyl)pyridine-3-boronic acid pinacol ester 5-(4-Tolyl)pyridine-3-boronic acid pinacol ester 1402172-15-9 C18H22BNO2
5-(5-Pyrimidyl)thiophene-2-boronic acid pinacol ester 5-(5-Pyrimidyl)thiophene-2-boronic acid pinacol ester 1402173-96-9 C15H19BN2O2S
5-(methyl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(methyl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241869-89-4 C12H18BNO2
5-Amino-2-(1H-pyrrol-1-yl)pyrimidine 5-Amino-2-(1H-pyrrol-1-yl)pyrimidine 1260788-70-2 C8H8N4
5-Amino-2-(2-thienyl)pyrimidine 5-Amino-2-(2-thienyl)pyrimidine 1152562-25-8 C8H7N3S
5-Amino-2-(cyclohexyloxy)thiazole 5-Amino-2-(cyclohexyloxy)thiazole 1314355-69-5 C9H14N2OS
5-Amino-4-(cyclobutyl)thiazole 5-Amino-4-(cyclobutyl)thiazole 1374664-29-5 C7H10N2S
5-Bromo-2-(1H-pyridin-2-one)thiazole 5-Bromo-2-(1H-pyridin-2-one)thiazole 959239-63-5 C8H5BrN2OS
5-Bromo-2-(3-thienyl)pyrimidine 5-Bromo-2-(3-thienyl)pyrimidine 1353856-96-8 C8H5BrN2S
5-Bromo-2-(n-propyl)pyrimidine 5-Bromo-2-(n-propyl)pyrimidine 1227960-44-2 C7H9BrN2
5-Bromo-2-(sec-butyl)pyrimidine 5-Bromo-2-(sec-butyl)pyrimidine 1563529-83-8 C8H11BrN2
5-Bromo-2-amino-4-(3-thienyl)pyridine 5-Bromo-2-amino-4-(3-thienyl)pyridine 1381941-72-5 C9H7BrN2S
5-BROMO-2-PROPYLPYRIDIN-4-AMINE 5-BROMO-2-PROPYLPYRIDIN-4-AMINE 1381937-85-4 C8H11BrN2
5-Bromo-3-cyclohexyl-2-(trifluoromethyl)pyridine 5-Bromo-3-cyclohexyl-2-(trifluoromethyl)pyridine 1622838-92-9 C12H13BrF3N
5-Bromo-4-ethylpyridine-2-boronic acid pinacol ester 5-Bromo-4-ethylpyridine-2-boronic acid pinacol ester 2223027-28-7 C13H19BBrNO2
5-Bromo-6-(2-methylpiperidin-1-yl)pyridine-3-boronic acid pinacol ester 5-Bromo-6-(2-methylpiperidin-1-yl)pyridine-3-boronic acid pinacol ester 1419478-33-3 C17H26BBrN2O2
5-Bromo-6-(3-cyanophenyl)pyridine-3-boronic acid pinacol ester 5-Bromo-6-(3-cyanophenyl)pyridine-3-boronic acid pinacol ester 2223039-19-6 C18H18BBrN2O2
5-Bromo-6-(pyridin-2-yl)pyridine-3-boronic acid pinacol ester 5-Bromo-6-(pyridin-2-yl)pyridine-3-boronic acid pinacol ester 2223030-85-9 C16H18BBrN2O2
5-bromo-N,N-bis(methyl-d3)pyridin-2-amine 5-bromo-N,N-bis(methyl-d3)pyridin-2-amine 1185312-37-1 C7H9BrN2
5-Cyclopropyl-6-methoxypyridine-3-boronic acid pinacol ester 5-Cyclopropyl-6-methoxypyridine-3-boronic acid pinacol ester 2223044-81-1 C15H22BNO3
5-Ethyl-2-trifluoromethylpyridine-4-boronic acid pinacol ester 5-Ethyl-2-trifluoromethylpyridine-4-boronic acid pinacol ester 2223033-62-1 C14H19BF3NO2
5-Fluoro-2-(4-methylimidazol-1-yl)pyridine-4-boronic acid pinacol ester 5-Fluoro-2-(4-methylimidazol-1-yl)pyridine-4-boronic acid pinacol ester 2223045-69-8 C15H19BFN3O2
5-Fluoro-2-(methoxycarbonyl)pyridine-4-boronic acid pinacol ester 5-Fluoro-2-(methoxycarbonyl)pyridine-4-boronic acid pinacol ester 1603136-85-1 C7H7BFNO4
5-Hydroxy-2-(3-thienyl)pyrimidine 5-Hydroxy-2-(3-thienyl)pyrimidine 1353856-30-0 C8H6N2OS
5-Hydroxy-2-(4-tolyl)pyrimidine 5-Hydroxy-2-(4-tolyl)pyrimidine 1260831-68-2 C11H10N2O
5-Methyl-2-(cyclopentyl)pyridine-4-boronic acid pinacol ester 5-Methyl-2-(cyclopentyl)pyridine-4-boronic acid pinacol ester 2223054-23-5 C17H26BNO2
5-methyl-2-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-methyl-2-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223012-10-8 C17H26BNO3
5-Methyl-6-ethylpyridine-3-boronic acid pinacol ester 5-Methyl-6-ethylpyridine-3-boronic acid pinacol ester 2223031-67-0 C14H22BNO2
6-(sec-butyl)-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 6-(sec-butyl)-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2222996-32-7 C15H23BFNO2
6-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 6-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 2222995-89-1 C16H25BN2O3
6-Bromo-5-(iso-propyl)pyridine-2-boronic acid pinacol ester 6-Bromo-5-(iso-propyl)pyridine-2-boronic acid pinacol ester 2223053-16-3 C14H21BBrNO2
6-Chloro-5-(2-chlorophenyl)pyridine-3-boronic acid pinacol ester 6-Chloro-5-(2-chlorophenyl)pyridine-3-boronic acid pinacol ester 2223028-95-1 C17H18BCl2NO2
6-Chloro-5-(2-thienyl)pyridine-3-boronic acid pinacol ester 6-Chloro-5-(2-thienyl)pyridine-3-boronic acid pinacol ester 2223038-88-6 C15H17BClNO2S
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