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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
2,6-Di(iso-propyl)pyrimidin-4-amine 2,6-Di(iso-propyl)pyrimidin-4-amine 1249629-26-2 C10H17N3
2-[Pyridazin-3(2H)-one]-5-bromothiazole 2-[Pyridazin-3(2H)-one]-5-bromothiazole 948846-82-0 C7H4BrN3OS
2-AMINO-3-(3-THIENYL)PYRIDINE 2-AMINO-3-(3-THIENYL)PYRIDINE 1417519-71-1 C9H8N2S
2-AMINO-3-(CYCLOBUTYL)PYRIDINE 2-AMINO-3-(CYCLOBUTYL)PYRIDINE 1417519-10-8 C9H12N2
2-Amino-3-bromo-5-(2-hydroxypiperidin-1-yl)pyridine 2-Amino-3-bromo-5-(2-hydroxypiperidin-1-yl)pyridine 1381936-08-8 C10H14BrN3O
2-Amino-3-bromo-5-(2-thienyl)pyridine 2-Amino-3-bromo-5-(2-thienyl)pyridine 1381936-69-1 C9H7BrN2S
2-amino-4-(1H-2-methylimidazol-1-yl)-6-(tert-butyl)pyrimidine 2-amino-4-(1H-2-methylimidazol-1-yl)-6-(tert-butyl)pyrimidine 1412954-65-4 C12H17N5
2-Amino-4-(1H-pyridin-2-one)-6-methylpyrimidine 2-Amino-4-(1H-pyridin-2-one)-6-methylpyrimidine 1412956-56-9 C10H10N4O
2-Amino-4-(1H-pyrrol-1-yl)-6-(iso-propyl)pyrimidine 2-Amino-4-(1H-pyrrol-1-yl)-6-(iso-propyl)pyrimidine 1412960-56-5 C11H14N4
2-Amino-4-(2-hydroxypiperidin-1-yl)pyrimidine 2-Amino-4-(2-hydroxypiperidin-1-yl)pyrimidine 1314354-68-1 C9H14N4O
2-amino-4-(2-methylpiperidin-1-yl)-6-cyclopropylpyrimidine 2-amino-4-(2-methylpiperidin-1-yl)-6-cyclopropylpyrimidine 1412960-72-5 C13H20N4
2-Amino-4-(3-chlorophenyl)-6-methylpyrimidine 2-Amino-4-(3-chlorophenyl)-6-methylpyrimidine 199865-33-3 C11H10ClN3
2-Amino-4-(3-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine 2-Amino-4-(3-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine 1412960-48-5 C9H11N5
2-Amino-4-(4-methyl-1H-imidazol-1-yl)-6-methylpyrimidine 2-Amino-4-(4-methyl-1H-imidazol-1-yl)-6-methylpyrimidine 1412961-47-7 C9H11N5
2-amino-4-(4-methylpiperidin-1-yl)-6-(tert-butyl)pyrimidine 2-amino-4-(4-methylpiperidin-1-yl)-6-(tert-butyl)pyrimidine 1070214-92-4 C14H24N4
2-Amino-4-(cyclopropyl)pyrimidine-5-boronic acid pinacol ester 2-Amino-4-(cyclopropyl)pyrimidine-5-boronic acid pinacol ester 2223031-78-3 C13H20BN3O2
2-Amino-4-(iso-propoxy)-6-cyclopropylpyrimidine 2-Amino-4-(iso-propoxy)-6-cyclopropylpyrimidine 1412955-69-1 C10H15N3O
2-amino-4-(pyridin-3-yl)-6-(tert-butyl)pyrimidine 2-amino-4-(pyridin-3-yl)-6-(tert-butyl)pyrimidine 100616-88-4 C13H16N4
2-Amino-4-(pyrimidin-5-yl)-6-(iso-propyl)pyrimidine 2-Amino-4-(pyrimidin-5-yl)-6-(iso-propyl)pyrimidine 1412957-27-7 C11H13N5
2-Amino-4-bromo-5-(2-hydroxypiperidin-1-yl)pyridine 2-Amino-4-bromo-5-(2-hydroxypiperidin-1-yl)pyridine 1381935-18-7 C10H14BrN3O
2-Amino-4-bromo-5-(cyclobutyl)pyridine 2-Amino-4-bromo-5-(cyclobutyl)pyridine 1357580-33-6 C9H11BrN2
2-Amino-4-bromo-5-(n-propyl)pyridine 2-Amino-4-bromo-5-(n-propyl)pyridine 1357580-49-4 C8H11BrN2
2-Amino-4-chloro-5-(3-thienyl)pyridine 2-Amino-4-chloro-5-(3-thienyl)pyridine 1381937-61-6 C9H7ClN2S
2-Amino-4-chloro-5-(4-pyridyl)pyridine 2-Amino-4-chloro-5-(4-pyridyl)pyridine 1381933-38-5 C10H8ClN3
2-Amino-4-cyclohexyl-6-methylpyrimidine 2-Amino-4-cyclohexyl-6-methylpyrimidine 1247372-96-8 C11H17N3
2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester 2-Amino-4-ethylpyrimidine-5-boronic acid pinacol ester 2223042-99-5 C12H20BN3O2
2-Amino-5-(5-pyrimidyl)pyrazine 2-Amino-5-(5-pyrimidyl)pyrazine 1159820-03-7 C8H7N5
2-Amino-5-bromo-4-(2-methoxyphenyl)pyridine 2-Amino-5-bromo-4-(2-methoxyphenyl)pyridine 1381943-17-4 C12H11BrN2O
2-Amino-5-bromo-4-(3-chlorophenyl)pyridine 2-Amino-5-bromo-4-(3-chlorophenyl)pyridine 1381942-65-9 C11H8BrClN2
2-Amino-5-bromo-4-(5-pyrimidyl)pyridine 2-Amino-5-bromo-4-(5-pyrimidyl)pyridine 1381934-37-7 C9H7BrN4
2-Amino-5-bromo-4-(imidazol-1-yl)pyridine 2-Amino-5-bromo-4-(imidazol-1-yl)pyridine 1381933-64-7 C8H7BrN4
2-AMINO-6-(METHOXYCARBONYL)PYRIDINE-4-BORONIC ACID PINACOL ESTER 2-AMINO-6-(METHOXYCARBONYL)PYRIDINE-4-BORONIC ACID PINACOL ESTER 2223044-78-6 C13H19BN2O4
2-Bromo-3-(2-methoxyphenyl)thiophene 2-Bromo-3-(2-methoxyphenyl)thiophene 1227959-32-1 C11H9BrOS
2-Bromo-3-(2-tolyl)furan 2-Bromo-3-(2-tolyl)furan 1227959-37-6 C11H9BrO
2-Bromo-3-(3-pyridyll)furan 2-Bromo-3-(3-pyridyll)furan 1227960-30-6 C9H6BrNO
2-Bromo-3-(3-trifluoromethylphenyl)furan 2-Bromo-3-(3-trifluoromethylphenyl)furan 1227960-25-9 C11H6BrF3O
2-Bromo-3-(4-trifluoromethylphenyl)pyridine 2-Bromo-3-(4-trifluoromethylphenyl)pyridine 1417519-13-1 C12H7BrF3N
2-Bromo-3-(cyclobutyl)furan 2-Bromo-3-(cyclobutyl)furan 1227959-16-1 C8H9BrO
2-Bromo-3-ethylfuran 2-Bromo-3-ethylfuran 1227960-29-3 C6H7BrO
2-Bromo-3-fluoro-4-cyclopropylpyridine 2-Bromo-3-fluoro-4-cyclopropylpyridine 1622839-15-9 C8H7BrFN
2-Bromo-3-methoxycarbonyl-4-(oxan-4-yl)pyridine 2-Bromo-3-methoxycarbonyl-4-(oxan-4-yl)pyridine 1622840-81-6 C12H14BrNO3
2-bromo-4-(1H-3-methylpyrozol-1-yl)-6-(tert-butyl)pyrimidine 2-bromo-4-(1H-3-methylpyrozol-1-yl)-6-(tert-butyl)pyrimidine 1412959-72-8 C12H15BrN4
2-Bromo-4-(1H-4-methylpyrozol-1-yl)-6-(iso-propyl)pyrimidine 2-Bromo-4-(1H-4-methylpyrozol-1-yl)-6-(iso-propyl)pyrimidine 1412960-02-1 C11H13BrN4
2-Bromo-4-(1H-pyridin-2-one)-6-cyclopropylpyrimidine 2-Bromo-4-(1H-pyridin-2-one)-6-cyclopropylpyrimidine 1412960-07-6 C12H10BrN3O
2-bromo-4-(1H-pyrozol-1-yl)-6-(tert-butyl)pyrimidine 2-bromo-4-(1H-pyrozol-1-yl)-6-(tert-butyl)pyrimidine 1412954-71-2 C11H13BrN4
2-bromo-4-(2-chlorophenyl)-6-cyclopropylpyrimidine 2-bromo-4-(2-chlorophenyl)-6-cyclopropylpyrimidine 1412953-55-9 C13H10BrClN2
2-bromo-4-(2-fluorophenyl)-6-cyclopropylpyrimidine 2-bromo-4-(2-fluorophenyl)-6-cyclopropylpyrimidine 1412954-90-5 C13H10BrFN2
2-Bromo-4-(2-methylimidazol-1-yl)pyrimidine 2-Bromo-4-(2-methylimidazol-1-yl)pyrimidine 1314353-48-4 C8H7BrN4
2-Bromo-4-(2-methylpiperidin-1-yl)-6-methylpyrimidine 2-Bromo-4-(2-methylpiperidin-1-yl)-6-methylpyrimidine 1412961-37-5 C11H16BrN3
2-Bromo-4-(2-tolyl)-6-(tert-butyl)pyrimidine 2-Bromo-4-(2-tolyl)-6-(tert-butyl)pyrimidine 1412955-19-1 C15H17BrN2
2-Bromo-4-(2-trifluoromethylphenyl)-1,3,5-triazine 2-Bromo-4-(2-trifluoromethylphenyl)-1,3,5-triazine 1417519-22-2 C10H5BrF3N3
2-bromo-4-(3-furyl)-6-(tert-butyl)pyrimidine 2-bromo-4-(3-furyl)-6-(tert-butyl)pyrimidine 1412958-04-3 C12H13BrN2O
2-Bromo-4-(3-methoxyphenyl)-1,3,5-triazine 2-Bromo-4-(3-methoxyphenyl)-1,3,5-triazine 1417518-39-8 C10H8BrN3O
2-Bromo-4-(3-thienyl)-1,3,5-triazine 2-Bromo-4-(3-thienyl)-1,3,5-triazine 1417519-62-0 C7H4BrN3S
2-Bromo-4-(4-fluorophenyl)-1,3,5-triazine 2-Bromo-4-(4-fluorophenyl)-1,3,5-triazine 1417519-20-0 C9H5BrFN3
2-Bromo-4-(4-pyridyl)pyrimidine 2-Bromo-4-(4-pyridyl)pyrimidine 1215071-41-2 C9H6BrN3
2-bromo-4-(cyclohexyl)-6-(tert-butyl)pyrimidine 2-bromo-4-(cyclohexyl)-6-(tert-butyl)pyrimidine 1412955-78-2 C14H21BrN2
2-Bromo-4-(cyclopropyl)-1,3,5-triazine 2-Bromo-4-(cyclopropyl)-1,3,5-triazine 1417518-23-0 C6H6BrN3
2-Bromo-4-(iso-propoxy)-6-(tert-butyl)pyrimidine 2-Bromo-4-(iso-propoxy)-6-(tert-butyl)pyrimidine 1412959-91-1 C11H17BrN2O
2-Bromo-4-(n-propyl)pyrimidine 2-Bromo-4-(n-propyl)pyrimidine 1215071-39-8 C7H9BrN2
2-bromo-4-(piperidin-1-yl)-6-cyclopropylpyrimidine 2-bromo-4-(piperidin-1-yl)-6-cyclopropylpyrimidine 1412954-69-8 C12H16BrN3
2-bromo-4-(pyridin-4-yl)-6-(tert-butyl)pyrimidine 2-bromo-4-(pyridin-4-yl)-6-(tert-butyl)pyrimidine 1412957-97-1 C13H14BrN3
2-Bromo-4-(pyrimidin-5-yl)-6-methylpyrimidine 2-Bromo-4-(pyrimidin-5-yl)-6-methylpyrimidine 1412961-30-8 C9H7BrN4
2-Bromo-4-(tert-butoxy)-6-methylpyrimidine 2-Bromo-4-(tert-butoxy)-6-methylpyrimidine 1412956-85-4 C9H13BrN2O
2-Bromo-4-(thiazol-4-yl)-1,3,5-triazine 2-Bromo-4-(thiazol-4-yl)-1,3,5-triazine 1417519-64-2 C6H3BrN4S
2-Bromo-4-chloro-5-(2-pyridyl)pyridine 2-Bromo-4-chloro-5-(2-pyridyl)pyridine 1381937-44-5 C10H6BrClN2
2-Bromo-4-chloro-5-(3-furyl)pyridine 2-Bromo-4-chloro-5-(3-furyl)pyridine 1381936-89-5 C9H5BrClNO
2-Bromo-4-chloro-5-phenylpyridine 2-Bromo-4-chloro-5-phenylpyridine 1381933-50-1 C11H7BrClN
2-Bromo-4-iodo-1,3,5-triazine 2-Bromo-4-iodo-1,3,5-triazine 1417519-25-5 C3HBrIN3
2-Bromo-5-(1H-pyrrol-1-yl)thiophene 2-Bromo-5-(1H-pyrrol-1-yl)thiophene 1622839-43-3 C8H6BrNS
2-Bromo-5-(2-chlorophenyl)furan 2-Bromo-5-(2-chlorophenyl)furan 1412955-93-1 C10H6BrClO
2-Bromo-5-(3-chlorophenyl)furan 2-Bromo-5-(3-chlorophenyl)furan 1412955-84-0 C10H6BrClO
2-Bromo-5-(3-tolyl)furan 2-Bromo-5-(3-tolyl)furan 89930-08-5 C11H9BrO
2-Bromo-5-(4-chlorophenyl)furan 2-Bromo-5-(4-chlorophenyl)furan 73226-76-3 C10H6BrClO
2-Bromo-5-(4-trifluoromethylphenyl)furan 2-Bromo-5-(4-trifluoromethylphenyl)furan 1412961-23-9 C11H6BrF3O
2-Bromo-5-(sec-butyl)furan 2-Bromo-5-(sec-butyl)furan 1412958-31-6 C8H11BrO
2-Bromo-5-cyclobutylpyridine-4-boronic acid pinacol ester 2-Bromo-5-cyclobutylpyridine-4-boronic acid pinacol ester 1402233-42-4 C15H21BBrNO2
2-Bromo-6-(2-methoxyphenyl)pyridine-4-boronic acid pinacol ester 2-Bromo-6-(2-methoxyphenyl)pyridine-4-boronic acid pinacol ester 2223040-42-2 C18H21BBrNO3
2-Bromo-6-(iso-propenyl) 
pyridine-4-boronic acid pinacol ester 2-Bromo-6-(iso-propenyl) pyridine-4-boronic acid pinacol ester 2223028-68-8 C14H19BBrNO2
2-Bromo-6-(thiazol-2-yl)pyridine-4-boronic acid pinacol ester 2-Bromo-6-(thiazol-2-yl)pyridine-4-boronic acid pinacol ester 2223035-91-2 C14H16BBrN2O2S
2-Bromo-6-ethylpyridine-4-boronic acid pinacol ester 2-Bromo-6-ethylpyridine-4-boronic acid pinacol ester 1402226-89-4 C13H19BBrNO2
2-Chloro-3-(2-tolyl)pyridine 2-Chloro-3-(2-tolyl)pyridine 1225883-90-8 C12H10ClN
2-Chloro-3-(3-furyl)pyridine 2-Chloro-3-(3-furyl)pyridine 1417518-51-4 C9H6ClNO
2-Chloro-3-(cyclopentyl)pyridine 2-Chloro-3-(cyclopentyl)pyridine 1417518-02-5 C10H12ClN
2-Chloro-3-cyano-4-(iso-propyl)pyridine 2-Chloro-3-cyano-4-(iso-propyl)pyridine 1448776-93-9 C9H9ClN2
2-chloro-4-(1H-4-methylpyrozol-1-yl)-6-cyclopropylpyrimidine 2-chloro-4-(1H-4-methylpyrozol-1-yl)-6-cyclopropylpyrimidine 1412960-32-7 C11H11ClN4
2-Chloro-4-(1H-pyrazol-1-yl)-6-methylpyrimidine 2-Chloro-4-(1H-pyrazol-1-yl)-6-methylpyrimidine 1248241-65-7 C8H7ClN4
2-chloro-4-(2-chlorophenyl)-6-cyclopropylpyrimidine 2-chloro-4-(2-chlorophenyl)-6-cyclopropylpyrimidine 1412953-62-8 C13H10Cl2N2
2-Chloro-4-(2-tolyl)pyrimidine 2-Chloro-4-(2-tolyl)pyrimidine 954216-68-3 C11H9ClN2
2-Chloro-4-(2-trifluoromethylphenyl)pyrimidine 2-Chloro-4-(2-trifluoromethylphenyl)pyrimidine 1142195-01-4 C11H6ClF3N2
2-Chloro-4-(3-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine 2-Chloro-4-(3-methyl-1H-pyrazol-1-yl)-6-methylpyrimidine 1248082-73-6 C9H9ClN4
2-Chloro-4-(3-methylpiperidin-1-yl)-6-(iso-propyl)pyrimidine 2-Chloro-4-(3-methylpiperidin-1-yl)-6-(iso-propyl)pyrimidine 1412953-87-7 C13H20ClN3
2-chloro-4-(4-chlorophenyl)-6-cyclopropylpyrimidine 2-chloro-4-(4-chlorophenyl)-6-cyclopropylpyrimidine 951231-17-7 C13H10Cl2N2
2-Chloro-4-(4-methoxyphenyl)-1,3,5-triazine 2-Chloro-4-(4-methoxyphenyl)-1,3,5-triazine 1417518-41-2 C10H8ClN3O
2-Chloro-4-(4-tetrahydropyranyl)-6-(iso-propyl)pyrimidine 2-Chloro-4-(4-tetrahydropyranyl)-6-(iso-propyl)pyrimidine 1412961-00-2 C12H17ClN2O
2-chloro-4-(cyclopentyl)-6-cyclopropylpyrimidine 2-chloro-4-(cyclopentyl)-6-cyclopropylpyrimidine 1412961-35-3 C12H15ClN2
2-Chloro-4-(n-propyl)-6-(iso-propyl)pyrimidine 2-Chloro-4-(n-propyl)-6-(iso-propyl)pyrimidine 1412954-92-7 C10H15ClN2
2-Chloro-4-(pyridin-4-yl)-6-(iso-propyl)pyrimidine 2-Chloro-4-(pyridin-4-yl)-6-(iso-propyl)pyrimidine 1412958-93-0 C12H12ClN3
2-chloro-4-(pyrimidin-5-yl)-6-cyclopropylpyrimidine 2-chloro-4-(pyrimidin-5-yl)-6-cyclopropylpyrimidine 1412956-68-3 C11H9ClN4
2-Chloro-4-(tert-butyl)-1,3,5-triazine 2-Chloro-4-(tert-butyl)-1,3,5-triazine 1417517-78-2 C7H10ClN3
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