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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
2,5-Dibromo-4-(2-fluorophenyl)thiazole 2,5-Dibromo-4-(2-fluorophenyl)thiazole 1314355-81-1 C9H4Br2FNS
2,5-Dibromo-4-(2-trifluoromethylphenyl)thiazole 2,5-Dibromo-4-(2-trifluoromethylphenyl)thiazole 1314355-87-7 C10H4Br2F3NS
2,5-Dibromo-4-(n-propyl)thiazole 2,5-Dibromo-4-(n-propyl)thiazole 1314353-81-5 C6H7Br2NS
2,5-dibromopyrimidine-4,6-d2 2,5-dibromopyrimidine-4,6-d2 2241865-49-4 C4H2Br2N2
2-Amino-3-(diethylamino)pyridine 2-Amino-3-(diethylamino)pyridine 1563530-86-8 C9H15N3
2-Amino-3,5-dibromo-4-(4-tolyl)pyridine 2-Amino-3,5-dibromo-4-(4-tolyl)pyridine 1563533-00-5 C12H10Br2N2
2-Amino-3,5-dibromo-4-phenylpyridine 2-Amino-3,5-dibromo-4-phenylpyridine 1563529-37-2 C11H8Br2N2
2-Amino-3-bromo-4-(3-fluorophenyl)pyridine 2-Amino-3-bromo-4-(3-fluorophenyl)pyridine 1381933-97-6 C11H8BrFN2
2-Amino-3-bromo-4-(3-methylpiperidin-1-yl)pyridine 2-Amino-3-bromo-4-(3-methylpiperidin-1-yl)pyridine 1381934-12-8 C11H16BrN3
2-Amino-3-bromo-4-(4-fluorophenyl)pyridine 2-Amino-3-bromo-4-(4-fluorophenyl)pyridine 1381942-97-7 C11H8BrFN2
2-Amino-3-bromo-4-(morpholino)pyridine 2-Amino-3-bromo-4-(morpholino)pyridine 1381934-20-8 C9H12BrN3O
2-Amino-4-(1-cyclohexene)thiazole 2-Amino-4-(1-cyclohexene)thiazole 1215071-74-1 C9H12N2S
2-Amino-4-(2-iso-propylpyrimidyl-5-yl)thiazole 2-Amino-4-(2-iso-propylpyrimidyl-5-yl)thiazole 1215072-25-5 C10H12N4S
2-Amino-4-(2-methyl-4-fluorophenyl)thiazole 2-Amino-4-(2-methyl-4-fluorophenyl)thiazole 23178-08-7 C10H9FN2S
2-Amino-4-(cyclopropyl)thiophene 2-Amino-4-(cyclopropyl)thiophene 1159821-74-5 C7H9NS
2-Amino-4-(iso-propyl)furan 2-Amino-4-(iso-propyl)furan 1159816-88-2 C7H11NO
2-Amino-4-(tetrahydropyran-3-yl)pyridine 2-Amino-4-(tetrahydropyran-3-yl)pyridine 1159814-93-3 C10H14N2O
2-Amino-4-bromo-3-(2-thienyl)pyridine 2-Amino-4-bromo-3-(2-thienyl)pyridine 1381941-75-8 C9H7BrN2S
2-Amino-4-chloro-3-(2-furyl)pyridine 2-Amino-4-chloro-3-(2-furyl)pyridine 1381937-27-4 C9H7ClN2O
2-Amino-4-chloro-3-ethylpyridine 2-Amino-4-chloro-3-ethylpyridine 1381934-84-4 C7H9ClN2
2-Amino-4-chloro-6-(2-furyl)-1,3,5-triazine 2-Amino-4-chloro-6-(2-furyl)-1,3,5-triazine 1303967-39-6 C7H5ClN4O
2-Amino-4-chloro-6-(3-furyl)pyrimidine 2-Amino-4-chloro-6-(3-furyl)pyrimidine 850250-62-3 C8H6ClN3O
2-Amino-4-chloro-6-(3-thienyl)-1,3,5-triazine 2-Amino-4-chloro-6-(3-thienyl)-1,3,5-triazine 1303967-99-8 C7H5ClN4S
2-Amino-5-(2-furyl)thiazole 2-Amino-5-(2-furyl)thiazole 100988-26-9 C7H6N2OS
2-Amino-5-(2-methoxyphenyl)thiophene 2-Amino-5-(2-methoxyphenyl)thiophene 1314353-95-1 C11H11NOS
2-Amino-5-(3,4-difluorophenyl)thiazole 2-Amino-5-(3,4-difluorophenyl)thiazole 1182820-77-4 C9H6F2N2S
2-AMINO-5-(3-FURAN)PYRIDINE 2-AMINO-5-(3-FURAN)PYRIDINE 1110657-42-5 C9H8N2O
2-Amino-5-(diethylamino)pyridine 2-Amino-5-(diethylamino)pyridine 151919-69-6 C9H15N3
2-Amino-5-(N-Boc-piperidin-3-yl)pyridine 2-Amino-5-(N-Boc-piperidin-3-yl)pyridine 1563529-74-7 C15H23N3O2
2-Amino-5-(tetrahydropyran-3-yl)pyridine 2-Amino-5-(tetrahydropyran-3-yl)pyridine 1159820-89-9 C10H14N2O
2-Amino-5-morpholinothiazole 2-Amino-5-morpholinothiazole 933696-76-5 C7H11N3OS
2-Amino-6-(tetrahydropyran-3-yl)pyridine 2-Amino-6-(tetrahydropyran-3-yl)pyridine 1159820-86-6 C10H14N2O
2-BROMO-3-(1H-IMIDAZOL-1-YL)PYRIDINE 2-BROMO-3-(1H-IMIDAZOL-1-YL)PYRIDINE 910454-06-7 C8H6BrN3
2-BROMO-3-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 2-BROMO-3-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 1563533-22-1 C9H8BrN3
2-bromo-4-(1H-pyrazol-1-yl-d3)pyridine-3,5,6-d3 2-bromo-4-(1H-pyrazol-1-yl-d3)pyridine-3,5,6-d3 2256707-34-1 C8BrD6N3
2-bromo-4-(2-bromophenyl)pyrimidine-5,6-d2 2-bromo-4-(2-bromophenyl)pyrimidine-5,6-d2 2256711-30-3 C10H6Br2N2
2-Bromo-4-(2-methoxyphenyl)thiophene 2-Bromo-4-(2-methoxyphenyl)thiophene 1159817-13-6 C11H9BrOS
2-Bromo-4-(2-pyridyl)pyridine 2-Bromo-4-(2-pyridyl)pyridine 1159817-75-0 C10H7BrN2
2-Bromo-4-(3,4-difluorophenyl)pyridine 2-Bromo-4-(3,4-difluorophenyl)pyridine 1215073-01-0 C11H6BrF2N
2-Bromo-4-(3-fluorophenyl)furan 2-Bromo-4-(3-fluorophenyl)furan 1159818-97-9 C10H6BrFO
2-Bromo-4-(3-tolyl)furan 2-Bromo-4-(3-tolyl)furan 1159818-77-5 C11H9BrO
2-bromo-4-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridine-3,5,6-d3 2-bromo-4-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)pyridine-3,5,6-d3 2294949-44-1 C9H8BrN3
2-Bromo-4-(4-ethylphenyl)pyridine 2-Bromo-4-(4-ethylphenyl)pyridine 1519824-79-3 C13H12BrN
2-Bromo-4-(4-isoxazolyl)pyridine 2-Bromo-4-(4-isoxazolyl)pyridine 1353855-13-6 C8H5BrN2O
2-Bromo-4-(acetoxy)pyridine 2-Bromo-4-(acetoxy)pyridine 1264033-85-3 C7H6BrNO2
2-Bromo-4-(tetrahydropyran-4-yl)pyridine 2-Bromo-4-(tetrahydropyran-4-yl)pyridine 1159814-84-2 C10H12BrNO
2-Bromo-4-amino-5-(2-pyridyl)pyridine 2-Bromo-4-amino-5-(2-pyridyl)pyridine 1381934-38-8 C10H8BrN3
2-Bromo-4-amino-5-(4-tolyl)pyridine 2-Bromo-4-amino-5-(4-tolyl)pyridine 1381934-08-2 C12H11BrN2
2-Bromo-4-amino-5-(n-propyl)pyrimidine 2-Bromo-4-amino-5-(n-propyl)pyrimidine 1381937-10-5 C7H10BrN3
2-Bromo-4-chloro-6-(3-furyl)pyrimidine 2-Bromo-4-chloro-6-(3-furyl)pyrimidine 1434127-38-4 C8H4BrClN2O
2-Bromo-4-chloro-6-(4-pyridyl)pyrimidine 2-Bromo-4-chloro-6-(4-pyridyl)pyrimidine 1434127-94-2 C9H5BrClN3
2-Bromo-5-(2-fluorophenyl)furan 2-Bromo-5-(2-fluorophenyl)furan 1159821-95-0 C10H6BrFO
2-Bromo-5-(2-furyl)pyrimidine 2-Bromo-5-(2-furyl)pyrimidine 1353853-92-5 C8H5BrN2O
2-Bromo-5-(2-methylpyrimidyl-5-yl)thiazole 2-Bromo-5-(2-methylpyrimidyl-5-yl)thiazole 1215072-22-2 C8H6BrN3S
2-Bromo-5-(2-thiazolyl)thiophene 2-Bromo-5-(2-thiazolyl)thiophene 263868-79-7 C7H4BrNS2
2-Bromo-5-(3,4-difluorophenyl)thiazole 2-Bromo-5-(3,4-difluorophenyl)thiazole 1215074-05-7 C9H4BrF2NS
2-Bromo-5-(3-aminophenyl)pyridine 2-Bromo-5-(3-aminophenyl)pyridine 1142193-89-2 C11H9BrN2
2-Bromo-5-(3-hydroxypiperidino)pyridine 2-Bromo-5-(3-hydroxypiperidino)pyridine 1314356-69-8 C10H13BrN2O
2-Bromo-5-(4-acetylphenyl)pyridine 2-Bromo-5-(4-acetylphenyl)pyridine 1142193-83-6 C13H10BrNO
2-Bromo-5-(4-chlorophenyl)pyrimidine 2-Bromo-5-(4-chlorophenyl)pyrimidine 1563534-93-9 C10H6BrClN2
2-Bromo-5-(4-fluorophenyl)pyridine 2-Bromo-5-(4-fluorophenyl)pyridine 868254-43-7 C11H7BrFN
2-Bromo-5-(4-tolyl)pyrimidine 2-Bromo-5-(4-tolyl)pyrimidine 1353856-33-3 C11H9BrN2
2-Bromo-5-(5-pyrimidyl)pyrimidine 2-Bromo-5-(5-pyrimidyl)pyrimidine 1353854-67-7 C8H5BrN4
2-Bromo-5-(iso-butyl)pyrimidine 2-Bromo-5-(iso-butyl)pyrimidine 1643542-16-8 C8H11BrN2
2-Bromo-5-(pyrimidyl-5-yl)thiazole 2-Bromo-5-(pyrimidyl-5-yl)thiazole 1215072-78-8 C7H4BrN3S
2-Bromo-5-(thiazol-2-yl)pyridine 2-Bromo-5-(thiazol-2-yl)pyridine 1211540-38-3 C8H5BrN2S
2-Bromo-5-amino-4-(2-thienyl)pyridine 2-Bromo-5-amino-4-(2-thienyl)pyridine 1381934-97-9 C9H7BrN2S
2-Bromo-5-amino-4-(3-furyl)pyridine 2-Bromo-5-amino-4-(3-furyl)pyridine 1381941-30-5 C9H7BrN2O
2-Bromo-5-amino-4-(cyclohexyl)pyridine 2-Bromo-5-amino-4-(cyclohexyl)pyridine 1381934-53-7 C11H15BrN2
2-Bromo-6-(3,4-difluorophenyl)pyridine 2-Bromo-6-(3,4-difluorophenyl)pyridine 1142196-99-3 C11H6BrF2N
2-Bromo-6-(3-tolyl)pyridine 2-Bromo-6-(3-tolyl)pyridine 1086381-57-8 C12H10BrN
2-bromopyridin-4,5,6-d3-3-ol 2-bromopyridin-4,5,6-d3-3-ol 1219843-92-1 C5H4BrNO
2-CHLORO-3-(2-AMINOPHENYL)PYRIDINE 2-CHLORO-3-(2-AMINOPHENYL)PYRIDINE 1563534-98-4 C11H9ClN2
2-Chloro-4-(2-pyridyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(2-pyridyl)-6-hydroxy-1,3,5-triazine 1303967-88-5 C8H5ClN4O
2-Chloro-4-(2-tolyl)-6-methoxy-1,3,5-triazine 2-Chloro-4-(2-tolyl)-6-methoxy-1,3,5-triazine 1303967-90-9 C11H10ClN3O
2-Chloro-4-(3-thienyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(3-thienyl)-6-hydroxy-1,3,5-triazine 1303967-30-7 C7H4ClN3OS
2-Chloro-4-(3-trifluoromethylphenyl)-6-methoxy-1,3,5-triazine 2-Chloro-4-(3-trifluoromethylphenyl)-6-methoxy-1,3,5-triazine 1303967-61-4 C11H7ClF3N3O
2-Chloro-4-(cyclobutyl)-6-(2-thienyl)-1,3,5-triazine 2-Chloro-4-(cyclobutyl)-6-(2-thienyl)-1,3,5-triazine 1227960-24-8 C11H10ClN3S
2-Chloro-4-(iso-propyl)-6-methoxy-1,3,5-triazine 2-Chloro-4-(iso-propyl)-6-methoxy-1,3,5-triazine 1303968-00-4 C7H10ClN3O
2-Chloro-4-amino-3-(2-tolyl)pyridine 2-Chloro-4-amino-3-(2-tolyl)pyridine 1381934-39-9 C12H11ClN2
2-CHLORO-4-AMINO-3-(3-FLUOROPHENYL)PYRIDINE 2-CHLORO-4-AMINO-3-(3-FLUOROPHENYL)PYRIDINE 1381935-24-5 C11H8ClFN2
2-Chloro-4-amino-3-(5-pyrimidyl)pyridine 2-Chloro-4-amino-3-(5-pyrimidyl)pyridine 1381934-86-6 C9H7ClN4
2-CHLORO-4-AMINO-3-(ISO-PROPYL)PYRIDINE 2-CHLORO-4-AMINO-3-(ISO-PROPYL)PYRIDINE 1381941-52-1 C8H11ClN2
2-Chloro-4-amino-5-(3-furyl)pyridine 2-Chloro-4-amino-5-(3-furyl)pyridine 1381936-10-2 C9H7ClN2O
2-Chloro-4-amino-5-(3-trifluoromethylphenyl)pyridine 2-Chloro-4-amino-5-(3-trifluoromethylphenyl)pyridine 1381934-79-7 C12H8ClF3N2
2-Chloro-4-amino-6-(2-thienyl)pyrimidine 2-Chloro-4-amino-6-(2-thienyl)pyrimidine 1353853-87-8 C8H6ClN3S
2-Chloro-4-amino-6-(cyclobutyl)pyrimidine 2-Chloro-4-amino-6-(cyclobutyl)pyrimidine 1353855-86-3 C8H10ClN3
2-Chloro-4-amino-6-(sec-butyl)pyrimidine 2-Chloro-4-amino-6-(sec-butyl)pyrimidine 1353853-45-8 C8H12ClN3
2-Chloro-4-bromo-6-(3-thienyl)pyrimidine 2-Chloro-4-bromo-6-(3-thienyl)pyrimidine 1412959-01-3 C8H4BrClN2S
2-Chloro-4-bromo-6-(4-methoxyphenyl)pyrimidine 2-Chloro-4-bromo-6-(4-methoxyphenyl)pyrimidine 1412953-73-1 C11H8BrClN2O
2-Chloro-4-bromo-6-(iso-propyl)pyrimidine 2-Chloro-4-bromo-6-(iso-propyl)pyrimidine 1412958-75-8 C7H8BrClN2
2-Chloro-4-bromo-6-ethyl-1,3,5-triazine 2-Chloro-4-bromo-6-ethyl-1,3,5-triazine 1399479-86-7 C5H5BrClN3
2-Chloro-4-cyclobutyl-6-hydroxy-1,3,5-triazine 2-Chloro-4-cyclobutyl-6-hydroxy-1,3,5-triazine 1303967-95-4 C7H8ClN3O
2-Chloro-5-(2-furyl)pyrimidine 2-Chloro-5-(2-furyl)pyrimidine 63558-66-7 C8H5ClN2O
2-Chloro-5-(3-thienyl)pyrimidine 2-Chloro-5-(3-thienyl)pyrimidine 169677-62-7 C8H5ClN2S
2-Chloro-5-(4-methylimidazol-1-yl)pyrimidine 2-Chloro-5-(4-methylimidazol-1-yl)pyrimidine 1363253-78-4 C8H7ClN4
2-Chloro-5-(piperidino)pyrimidine 2-Chloro-5-(piperidino)pyrimidine 1363254-09-4 C9H12ClN3
2-Hydroxy-4-(2-furyl)thiazole 2-Hydroxy-4-(2-furyl)thiazole 1095231-43-8 C7H5NO2S
2-Hydroxy-4-(3-thienyl)pyridine 2-Hydroxy-4-(3-thienyl)pyridine 1159820-97-9 C9H7NOS
2-Hydroxy-4-(4-fluorophenyl)thiophene 2-Hydroxy-4-(4-fluorophenyl)thiophene 1243838-87-0 C10H7FOS
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