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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-(4-fluorophenyl)thiazole 2,5-Dibromo-4-(4-fluorophenyl)thiazole 1357580-30-3 C9H4Br2FNS
2,5-Dibromo-4-(cyclobutyl)thiazole 2,5-Dibromo-4-(cyclobutyl)thiazole 1314354-06-7 C7H7Br2NS
2-[3-(TRIFLUOROMETHYL)PHENYL]PYRIDIN-4-AMINE 2-[3-(TRIFLUOROMETHYL)PHENYL]PYRIDIN-4-AMINE 1215073-24-7 C12H9F3N2
2-Amino-3,5-dibromo-4-(3-trifluoromethylphenyl)pyridine 2-Amino-3,5-dibromo-4-(3-trifluoromethylphenyl)pyridine 1563533-01-6 C12H7Br2F3N2
2-Amino-3-bromo-4-(2-furyl)pyridine 2-Amino-3-bromo-4-(2-furyl)pyridine 1381938-49-3 C9H7BrN2O
2-Amino-3-bromo-4-(2-pyridyl)pyridine 2-Amino-3-bromo-4-(2-pyridyl)pyridine 1381943-74-3 C10H8BrN3
2-Amino-3-bromo-4-(4-chlorophenyl)pyridine 2-Amino-3-bromo-4-(4-chlorophenyl)pyridine 1381941-63-4 C11H8BrClN2
2-Amino-3-bromo-4-(cyclobutyl)pyridine 2-Amino-3-bromo-4-(cyclobutyl)pyridine 1381937-90-1 C9H11BrN2
2-Amino-4-(2-amino-5-pyrimidyl)thiazole 2-Amino-4-(2-amino-5-pyrimidyl)thiazole 1215074-34-2 C7H7N5S
2-Amino-4-(2-cyclobutylpyrimidyl-5-yl)thiazole 2-Amino-4-(2-cyclobutylpyrimidyl-5-yl)thiazole 1215071-31-0 C11H12N4S
2-AMINO-4-(CYCLOPENTOXY)PYRIDINE 2-AMINO-4-(CYCLOPENTOXY)PYRIDINE 1314355-51-5 C10H14N2O
2-Amino-4-bromo-3-(3-thienyl)pyridine 2-Amino-4-bromo-3-(3-thienyl)pyridine 1381942-95-5 C9H7BrN2S
2-Amino-4-bromo-3-(4-pyridyl)pyridine 2-Amino-4-bromo-3-(4-pyridyl)pyridine 1381934-60-6 C10H8BrN3
2-Amino-4-chloro-3-(3-tolyl)pyridine 2-Amino-4-chloro-3-(3-tolyl)pyridine 1381933-65-8 C12H11ClN2
2-Amino-4-chloro-6-(2-pyridyl)pyrimidine 2-Amino-4-chloro-6-(2-pyridyl)pyrimidine 569657-98-3 C9H7ClN4
2-Amino-4-chloro-6-(2-trifluoromethylphenyl)pyrimidine 2-Amino-4-chloro-6-(2-trifluoromethylphenyl)pyrimidine 774608-21-8 C11H7ClF3N3
2-Amino-4-chloro-6-(3-trifluoromethylphenyl)pyrimidine 2-Amino-4-chloro-6-(3-trifluoromethylphenyl)pyrimidine 1353854-42-8 C11H7ClF3N3
2-Amino-4-chloro-6-(4-tolyl)-1,3,5-triazine 2-Amino-4-chloro-6-(4-tolyl)-1,3,5-triazine 1303968-04-8 C10H9ClN4
2-Amino-5-(2-cyclobutylpyrimidyl-5-yl)thiazole 2-Amino-5-(2-cyclobutylpyrimidyl-5-yl)thiazole 1215071-56-9 C11H12N4S
2-Amino-5-(2-methylpyrimidyl-5-yl)thiazole 2-Amino-5-(2-methylpyrimidyl-5-yl)thiazole 1215072-02-8 C8H8N4S
2-Amino-5-(2-trifluoromethylphenyl)furan 2-Amino-5-(2-trifluoromethylphenyl)furan 1643564-02-6 C11H8F3NO
2-Amino-5-(3-methoxylphenyl)pyrimidine 2-Amino-5-(3-methoxylphenyl)pyrimidine 947592-42-9 C11H11N3O
2-Amino-5-(3-pyridyl)pyrimidine 2-Amino-5-(3-pyridyl)pyrimidine 1111112-11-8 C9H8N4
2-Amino-5-(cyclobutyl)thiophene 2-Amino-5-(cyclobutyl)thiophene 1314357-02-2 C8H11NS
2-Amino-5-(piperidin-3-yl)pyrimidine 2-Amino-5-(piperidin-3-yl)pyrimidine 1368377-33-6 C9H14N4
2-AMINO-6-(2-FURYL)PYRIDINE 2-AMINO-6-(2-FURYL)PYRIDINE 167023-55-4 C9H8N2O
2-Amino-6-(2-methylthiazol-4-yl)pyridine 2-Amino-6-(2-methylthiazol-4-yl)pyridine 1159820-30-0 C9H9N3S
2-Amino-6-(N-Boc-Piperidin-3-yl)pyridine 2-Amino-6-(N-Boc-Piperidin-3-yl)pyridine 1563529-70-3 C15H23N3O2
2-Amino-6-(piperidin-3-yl)pyridine 2-Amino-6-(piperidin-3-yl)pyridine 1260868-40-3 C10H15N3
2-BROMO-3-(2-CHLOROPHENYL)PYRIDINE 2-BROMO-3-(2-CHLOROPHENYL)PYRIDINE 1563533-56-1 C11H7BrClN
2-BROMO-3-(3-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 2-BROMO-3-(3-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 1563533-16-3 C9H8BrN3
2-Bromo-4-(2-fluorophenyl)furan 2-Bromo-4-(2-fluorophenyl)furan 1159817-45-4 C10H6BrFO
2-Bromo-4-(2-thiazolyl)pyridine 2-Bromo-4-(2-thiazolyl)pyridine 1353857-01-8 C8H5BrN2S
2-Bromo-4-(2-tolyl)pyridine 2-Bromo-4-(2-tolyl)pyridine 1142197-07-6 C12H10BrN
2-Bromo-4-(3-furyl)thiazole 2-Bromo-4-(3-furyl)thiazole 1215073-17-8 C7H4BrNOS
2-Bromo-4-(3-pyridyl)pyridine 2-Bromo-4-(3-pyridyl)pyridine 1159817-79-4 C10H7BrN2
2-Bromo-4-(4-methyl-1H-pyrazol-1yl)pyridine 2-Bromo-4-(4-methyl-1H-pyrazol-1yl)pyridine 1159815-55-0 C9H8BrN3
2-Bromo-4-(4-tolyl)furan 2-Bromo-4-(4-tolyl)furan 1159818-85-5 C11H9BrO
2-Bromo-4-(cyclohexyl)furan 2-Bromo-4-(cyclohexyl)furan 1159818-67-3 C10H13BrO
2-Bromo-4-(cyclopentyl)furan 2-Bromo-4-(cyclopentyl)furan 1159818-60-6 C9H11BrO
2-Bromo-4-(tert-butyl)furan 2-Bromo-4-(tert-butyl)furan 1369131-10-1 C8H11BrO
2-Bromo-4-amino-5-(3-fluorophenyl)pyridine 2-Bromo-4-amino-5-(3-fluorophenyl)pyridine 1381936-03-3 C11H8BrFN2
2-Bromo-4-amino-5-(3-tolyl)pyridine 2-Bromo-4-amino-5-(3-tolyl)pyridine 1381938-29-9 C12H11BrN2
2-bromo-4-chloro-3-iodopyridine-5,6-d2 2-bromo-4-chloro-3-iodopyridine-5,6-d2 2294948-94-8 C5BrClD2IN
2-Bromo-5-(1-cyclohexenyl)pyridine 2-Bromo-5-(1-cyclohexenyl)pyridine 1142193-69-8 C11H12BrN
2-Bromo-5-(2-amino-5-pyridyl)pyridine 2-Bromo-5-(2-amino-5-pyridyl)pyridine 1142193-96-1 C10H8BrN3
2-Bromo-5-(2-chlorophenyl)thiazole 2-Bromo-5-(2-chlorophenyl)thiazole 1353855-62-5 C9H5BrClNS
2-Bromo-5-(2-methoxyphenyl)furan 2-Bromo-5-(2-methoxyphenyl)furan 1159818-37-7 C11H9BrO2
2-Bromo-5-(2-methyl-4-fluorophenyl)thiazole 2-Bromo-5-(2-methyl-4-fluorophenyl)thiazole 1215073-06-5 C10H7BrFNS
2-Bromo-5-(2-tolyl)pyridine 2-Bromo-5-(2-tolyl)pyridine 1142197-31-6 C12H10BrN
2-Bromo-5-(3-chlorophenyl)pyrimidine 2-Bromo-5-(3-chlorophenyl)pyrimidine 1563534-10-0 C10H6BrClN2
2-Bromo-5-(3-fluorophenyl)pyrimidine 2-Bromo-5-(3-fluorophenyl)pyrimidine 1353855-95-4 C10H6BrFN2
2-Bromo-5-(3-tolyl)pyrimidine 2-Bromo-5-(3-tolyl)pyrimidine 1353855-02-3 C11H9BrN2
2-Bromo-5-(4-aminophenyl)pyridine 2-Bromo-5-(4-aminophenyl)pyridine 1142193-87-0 C11H9BrN2
2-Bromo-5-(cyclohexyl)pyridine 2-Bromo-5-(cyclohexyl)pyridine 1142197-23-6 C11H14BrN
2-Bromo-5-(tert-butyl)furan 2-Bromo-5-(tert-butyl)furan 1080642-30-3 C8H11BrO
2-Bromo-5-amino-4-(2-hydroxypiperidin-1-yl)pyridine 2-Bromo-5-amino-4-(2-hydroxypiperidin-1-yl)pyridine 1381942-38-6 C10H14BrN3O
2-Bromo-5-amino-4-(3-pyridyl)pyridine 2-Bromo-5-amino-4-(3-pyridyl)pyridine 1381934-87-7 C10H8BrN3
2-Bromo-5-amino-4-(4-hydroxypiperidin-1-yl)pyridine 2-Bromo-5-amino-4-(4-hydroxypiperidin-1-yl)pyridine 1381934-22-0 C10H14BrN3O
2-Bromo-5-amino-4-(morpholino)pyridine 2-Bromo-5-amino-4-(morpholino)pyridine 1381934-82-2 C9H12BrN3O
2-Bromo-5-cyclobutylpyrimidine 2-Bromo-5-cyclobutylpyrimidine 1353855-98-7 C8H9BrN2
2-bromo-6-(1H-pyrazol-1-yl-d3)pyridine 2-bromo-6-(1H-pyrazol-1-yl-d3)pyridine 2256707-44-3 C8H6BrN3
2-Bromo-6-(3-fluorophenyl)pyridine 2-Bromo-6-(3-fluorophenyl)pyridine 1142196-77-7 C11H7BrFN
2-Bromo-6-(3-pyridyl)pyrazine 2-Bromo-6-(3-pyridyl)pyrazine 1159822-08-8 C9H6BrN3
2-Bromol-4-amino-5-(3-furyl)pyrimidine 2-Bromol-4-amino-5-(3-furyl)pyrimidine 1381935-53-0 C8H6BrN3O
2-Chloro-4-(2-chloro-5-thiazolyl)pyridine 2-Chloro-4-(2-chloro-5-thiazolyl)pyridine 959986-21-1 C8H4Cl2N2S
2-Chloro-4-(2-methoxyphenyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(2-methoxyphenyl)-6-hydroxy-1,3,5-triazine 1303967-97-6 C10H8ClN3O2
2-Chloro-4-(3,5-difluorophenyl)thiazole 2-Chloro-4-(3,5-difluorophenyl)thiazole 1188123-24-1 C9H4ClF2NS
2-Chloro-4-(3-methoxyphenyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(3-methoxyphenyl)-6-hydroxy-1,3,5-triazine 1303967-86-3 C10H8ClN3O2
2-Chloro-4-(4-methoxyphenyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(4-methoxyphenyl)-6-hydroxy-1,3,5-triazine 1303967-28-3 C10H8ClN3O2
2-Chloro-4-(4-tetrahydropyranyl)pyridine 2-Chloro-4-(4-tetrahydropyranyl)pyridine 1381941-42-9 C10H12ClNO
2-Chloro-4-amino-3-(2-chlorophenyl)pyridine 2-Chloro-4-amino-3-(2-chlorophenyl)pyridine 1381938-11-9 C11H8Cl2N2
2-CHLORO-4-AMINO-3-(3-TOLYL)PYRIDINE 2-CHLORO-4-AMINO-3-(3-TOLYL)PYRIDINE 1381933-23-8 C12H11ClN2
2-CHLORO-4-AMINO-3-(4-FLUOROPHENYL)PYRIDINE 2-CHLORO-4-AMINO-3-(4-FLUOROPHENYL)PYRIDINE 1381938-72-2 C11H8ClFN2
2-CHLORO-4-AMINO-3-ETHYLPYRIDINE 2-CHLORO-4-AMINO-3-ETHYLPYRIDINE 1381938-01-7 C7H9ClN2
2-Chloro-4-amino-5-(2-thienyl)pyridine 2-Chloro-4-amino-5-(2-thienyl)pyridine 1381942-17-1 C9H7ClN2S
2-Chloro-4-amino-5-(4-trifluoromethylphenyl)pyridine 2-Chloro-4-amino-5-(4-trifluoromethylphenyl)pyridine 1381941-20-3 C12H8ClF3N2
2-Chloro-4-amino-6-(3-furyl)pyrimidine 2-Chloro-4-amino-6-(3-furyl)pyrimidine 1353855-91-0 C8H6ClN3O
2-Chloro-4-amino-6-(4-chlorophenyl)pyrimidine 2-Chloro-4-amino-6-(4-chlorophenyl)pyrimidine 1353856-92-4 C10H7Cl2N3
2-Chloro-4-bromo-6-(2-methoxyphenyl)pyrimidine 2-Chloro-4-bromo-6-(2-methoxyphenyl)pyrimidine 1412956-50-3 C11H8BrClN2O
2-Chloro-4-bromo-6-(3-chlorophenyl)pyrimidine 2-Chloro-4-bromo-6-(3-chlorophenyl)pyrimidine 1412960-24-7 C10H5BrCl2N2
2-Chloro-4-bromo-6-(5-pyrimidyl)pyrimidine 2-Chloro-4-bromo-6-(5-pyrimidyl)pyrimidine 1412959-10-4 C8H4BrClN4
2-Chloro-4-bromo-6-(cyclohexyl)pyrimidine 2-Chloro-4-bromo-6-(cyclohexyl)pyrimidine 1412958-92-9 C10H12BrClN2
2-Chloro-4-cyclobutyl-6-amino-1,3,5-triazine 2-Chloro-4-cyclobutyl-6-amino-1,3,5-triazine 1139245-02-5 C7H9ClN4
2-Chloro-4-cyclopentyl-6-methoxy-1,3,5-triazine 2-Chloro-4-cyclopentyl-6-methoxy-1,3,5-triazine 1303967-85-2 C9H12ClN3O
2-Chloro-4-ethyl-6-methoxy-1,3,5-triazine 2-Chloro-4-ethyl-6-methoxy-1,3,5-triazine 937-43-9 C6H8ClN3O
2-CHLORO-5-(2-TOLYL)PYRIMIDINE 2-CHLORO-5-(2-TOLYL)PYRIMIDINE 1048338-29-9 C11H9ClN2
2-Chloro-5-(cyclobutoxy)pyrimidine 2-Chloro-5-(cyclobutoxy)pyrimidine 1363253-91-1 C8H9ClN2O
2-Chloro-5-(cyclopentyl)pyrimidine 2-Chloro-5-(cyclopentyl)pyrimidine 1353855-89-6 C9H11ClN2
2-chloro-5-(tetrahydrofuran-2-yl)pyrimidine 2-chloro-5-(tetrahydrofuran-2-yl)pyrimidine 2222933-85-7 C8H9ClN2O
2-Chloro-6-(2-methoxyphenyl)-4-methylpyrimidine 2-Chloro-6-(2-methoxyphenyl)-4-methylpyrimidine 219840-89-8 C12H11ClN2O
2-CYCLOHEXYLPYRIDIN-4-AMINE 2-CYCLOHEXYLPYRIDIN-4-AMINE 1159817-15-8 C11H16N2
2-cyclopropoxy-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-cyclopropoxy-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2256758-20-8 C13H20BNO3S
2-Ethyl-5-hydroxythiazole 2-Ethyl-5-hydroxythiazole 1159819-20-1 C5H7NOS
2-fluoro-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-2-yl)pyridine 2-fluoro-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-2-yl)pyridine 2256755-53-8 C14H17BFN3O2
2-Hydroxy-4-(2-cyclobutylpyrimidyl-5-yl)thiazole 2-Hydroxy-4-(2-cyclobutylpyrimidyl-5-yl)thiazole 1215073-54-3 C11H11N3OS
2-Hydroxy-4-(3,4-difluorophenyl)thiazole 2-Hydroxy-4-(3,4-difluorophenyl)thiazole 1095198-43-8 C9H5F2NOS
2-Hydroxy-4-(3-furyl)pyridine 2-Hydroxy-4-(3-furyl)pyridine 1159818-16-2 C9H7NO2
2-Hydroxy-4-(5-pyrimidyl)pyridine 2-Hydroxy-4-(5-pyrimidyl)pyridine 1159817-93-2 C9H7N3O
2-Hydroxy-4-(cyclopentyl)thiazole 2-Hydroxy-4-(cyclopentyl)thiazole 1215073-92-9 C8H11NOS
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