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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
2,4-Dichloro-5-(thiazol-4-yl)pyrimidine 2,4-Dichloro-5-(thiazol-4-yl)pyrimidine 1622843-76-8 C7H3Cl2N3S
2,4-Dichloro-6-(2-thienyl)-1,3,5-triazine 2,4-Dichloro-6-(2-thienyl)-1,3,5-triazine 2854-76-4 C7H3Cl2N3S
2,4-Dichloro-6-(4-pyridyl)-1,3,5-triazine 2,4-Dichloro-6-(4-pyridyl)-1,3,5-triazine 1227959-03-6 C8H4Cl2N4
2,4-Dichloro-6-(5-iso-propyl-2-thienyl)-1,3,5-triazine 2,4-Dichloro-6-(5-iso-propyl-2-thienyl)-1,3,5-triazine 1227959-12-7 C10H9Cl2N3S
2,5-Dibromo-4-(2-furyl)thiazole 2,5-Dibromo-4-(2-furyl)thiazole 1357580-40-5 C7H3Br2NOS
2,5-Dibromo-4-(cyclohexyl)thiazole 2,5-Dibromo-4-(cyclohexyl)thiazole 1314353-83-7 C9H11Br2NS
2-Amino-3-(methylethylamino)pyridine 2-Amino-3-(methylethylamino)pyridine 1563533-12-9 C8H13N3
2-Amino-3,5-dibromo-4-(4-chlorophenyl)pyridine 2-Amino-3,5-dibromo-4-(4-chlorophenyl)pyridine 1563529-76-9 C11H7Br2ClN2
2-Amino-3,5-dibromo-4-(4-trifluoromethylphenyl)pyridine 2-Amino-3,5-dibromo-4-(4-trifluoromethylphenyl)pyridine 1563532-12-6 C12H7Br2F3N2
2-Amino-3-bromo-4-(2-thienyl)pyridine 2-Amino-3-bromo-4-(2-thienyl)pyridine 1381938-02-8 C9H7BrN2S
2-Amino-3-bromo-4-(3-furyl)pyridine 2-Amino-3-bromo-4-(3-furyl)pyridine 1381941-49-6 C9H7BrN2O
2-Amino-3-bromo-4-(cyclohexyl)pyridine 2-Amino-3-bromo-4-(cyclohexyl)pyridine 1381942-63-7 C11H15BrN2
2-Amino-4-(2-cyclopropylpyrimidyl-5-yl)thiazole 2-Amino-4-(2-cyclopropylpyrimidyl-5-yl)thiazole 1215071-43-4 C10H10N4S
2-AMINO-4-(CYCLOBUTOXY)PYRIDINE 2-AMINO-4-(CYCLOBUTOXY)PYRIDINE 1314354-74-9 C9H12N2O
2-Amino-4-(piperidin-3-yl)pyrimidine 2-Amino-4-(piperidin-3-yl)pyrimidine 1250024-30-6 C9H14N4
2-Amino-4-bromo-3-(4-tolyl)pyridine 2-Amino-4-bromo-3-(4-tolyl)pyridine 1381941-87-2 C12H11BrN2
2-Amino-4-chloro-3-(3-trifluoromethylphenyl)pyridine 2-Amino-4-chloro-3-(3-trifluoromethylphenyl)pyridine 1381934-06-0 C12H8ClF3N2
2-Amino-4-chloro-3-(cyclobutyl)pyridine 2-Amino-4-chloro-3-(cyclobutyl)pyridine 1381941-84-9 C9H11ClN2
2-Amino-4-chloro-6-(2-thienyl)-1,3,5-triazine 2-Amino-4-chloro-6-(2-thienyl)-1,3,5-triazine 1303968-03-7 C7H5ClN4S
2-Amino-4-chloro-6-(3-chlorophenyl)pyrimidine 2-Amino-4-chloro-6-(3-chlorophenyl)pyrimidine 774608-22-9 C10H7Cl2N3
2-Amino-4-chloro-6-(4-fluorophenyl)-1,3,5-triazine 2-Amino-4-chloro-6-(4-fluorophenyl)-1,3,5-triazine 1303967-82-9 C9H6ClFN4
2-Amino-4-chloro-6-(4-tolyl)pyrimidine 2-Amino-4-chloro-6-(4-tolyl)pyrimidine 862168-08-9 C11H10ClN3
2-Amino-5-(2-cyclopropylpyrimidyl-5-yl)thiazole 2-Amino-5-(2-cyclopropylpyrimidyl-5-yl)thiazole 1215073-61-2 C10H10N4S
2-Amino-5-(cyclohexyl)pyrimidine 2-Amino-5-(cyclohexyl)pyrimidine 73549-64-1 C10H15N3
2-Amino-6-(2-pyridyl)pyrazine 2-Amino-6-(2-pyridyl)pyrazine 925677-96-9 C9H8N4
2-AMINO-6-(5-THIAZOLYL)PYRIDINE 2-AMINO-6-(5-THIAZOLYL)PYRIDINE 1563533-77-6 C8H7N3S
2-BROMO-3-(3-METHYLPIPERIDIN-1-YL)PYRIDINE 2-BROMO-3-(3-METHYLPIPERIDIN-1-YL)PYRIDINE 1563531-00-9 C11H15BrN2
2-BROMO-3-(4-METHYLIMIDAZOL-1-YL)PYRIDINE 2-BROMO-3-(4-METHYLIMIDAZOL-1-YL)PYRIDINE 1563535-03-4 C9H8BrN3
2-Bromo-4-(1H-pyridin-2-one)pyridine 2-Bromo-4-(1H-pyridin-2-one)pyridine 1142194-72-6 C10H7BrN2O
2-Bromo-4-(2-iso-propylpyrimidyl-5-yl)thiazole 2-Bromo-4-(2-iso-propylpyrimidyl-5-yl)thiazole 1215072-38-0 C10H10BrN3S
2-Bromo-4-(3,4-difluorophenyl)thiazole 2-Bromo-4-(3,4-difluorophenyl)thiazole 1188041-08-8 C9H4BrF2NS
2-bromo-4-(4-bromophenyl)pyrimidine-5,6-d2 2-bromo-4-(4-bromophenyl)pyrimidine-5,6-d2 2256712-13-5 C10H6Br2N2
2-Bromo-4-(cyclohexyl)pyridine 2-Bromo-4-(cyclohexyl)pyridine 1142197-06-5 C11H14BrN
2-Bromo-4-(cyclopentyl)pyridine 2-Bromo-4-(cyclopentyl)pyridine 1142197-03-2 C10H12BrN
2-Bromo-4-(N-Boc-piperidin-3-yl)pyridine 2-Bromo-4-(N-Boc-piperidin-3-yl)pyridine 1563531-53-2 C15H21BrN2O2
2-Bromo-4-(tert-butyl)thiophine 2-Bromo-4-(tert-butyl)thiophine 53119-65-6 C8H11BrS
2-Bromo-4-amino-5-(3-furyl)pyridine 2-Bromo-4-amino-5-(3-furyl)pyridine 1381933-76-1 C9H7BrN2O
2-Bromo-4-amino-5-(3-trifluoromethylphenyl)pyridine 2-Bromo-4-amino-5-(3-trifluoromethylphenyl)pyridine 1381940-90-4 C12H8BrF3N2
2-Bromo-4-chloro-6-(2-fluorophenyl)pyrimidine 2-Bromo-4-chloro-6-(2-fluorophenyl)pyrimidine 1434127-43-1 C10H5BrClFN2
2-Bromo-4-chloro-6-(2-trifluoromethylphenyl)pyrimidine 2-Bromo-4-chloro-6-(2-trifluoromethylphenyl)pyrimidine 1434128-40-1 C11H5BrClF3N2
2-Bromo-4-phenylfuran 2-Bromo-4-phenylfuran 1159816-94-0 C10H7BrO
2-BROMO-5-(2-CYANOPHENYL)PYRIDINE 2-BROMO-5-(2-CYANOPHENYL)PYRIDINE 1391737-79-3 C12H7BrN2
2-Bromo-5-(2-methylimidazol-1-yl)pyridine 2-Bromo-5-(2-methylimidazol-1-yl)pyridine 1314354-33-0 C9H8BrN3
2-Bromo-5-(2-methylthiazol-4-yl)pyridine 2-Bromo-5-(2-methylthiazol-4-yl)pyridine 1142197-28-1 C9H7BrN2S
2-Bromo-5-(2-trifluoromethylphenyl)pyrimidine 2-Bromo-5-(2-trifluoromethylphenyl)pyrimidine 1353856-75-3 C11H6BrF3N2
2-Bromo-5-(3-furyl)pyridine 2-Bromo-5-(3-furyl)pyridine 1142193-62-1 C9H6BrNO
2-Bromo-5-(3-hydroxypyrrolidino)pyridine 2-Bromo-5-(3-hydroxypyrrolidino)pyridine 1314356-68-7 C9H11BrN2O
2-Bromo-5-(3-tolyl)thiazole 2-Bromo-5-(3-tolyl)thiazole 1215073-84-9 C10H8BrNS
2-Bromo-5-(4-pyridyl)pyrimidine 2-Bromo-5-(4-pyridyl)pyrimidine 1353855-48-7 C9H6BrN3
2-Bromo-5-(cyclohexyloxy)pyridine 2-Bromo-5-(cyclohexyloxy)pyridine 1353855-92-1 C11H14BrNO
2-Bromo-5-(cyclopropyl)furan 2-Bromo-5-(cyclopropyl)furan 1159821-64-3 C7H7BrO
2-Bromo-5-amino-4-(1H-pyrazol-1-yl)pyridine 2-Bromo-5-amino-4-(1H-pyrazol-1-yl)pyridine 1381937-62-7 C8H7BrN4
2-Bromo-5-amino-4-(2-methoxyphenyl)pyridine 2-Bromo-5-amino-4-(2-methoxyphenyl)pyridine 1381937-78-5 C12H11BrN2O
2-Bromo-5-amino-4-(3-thienyl)pyridine 2-Bromo-5-amino-4-(3-thienyl)pyridine 1381934-10-6 C9H7BrN2S
2-Bromo-5-amino-4-(4-methoxyphenyl)pyridine 2-Bromo-5-amino-4-(4-methoxyphenyl)pyridine 1381937-94-5 C12H11BrN2O
2-Bromo-5-cyclohexylpyrimidine 2-Bromo-5-cyclohexylpyrimidine 1353855-83-0 C10H13BrN2
2-bromo-6-(1H-imidazol-1-yl-d3)pyridine 2-bromo-6-(1H-imidazol-1-yl-d3)pyridine 2256707-28-3 C8H6BrN3
2-bromo-6-(1H-pyrazol-1-yl-d3)pyridine-3,4,5-d3 2-bromo-6-(1H-pyrazol-1-yl-d3)pyridine-3,4,5-d3 2256707-45-4 C8BrD6N3
2-Bromo-6-(2-methylthiazol-4-yl)pyridine 2-Bromo-6-(2-methylthiazol-4-yl)pyridine 142978-12-9 C9H7BrN2S
2-Bromo-6-(4-pyridyl)pyrazine 2-Bromo-6-(4-pyridyl)pyrazine 1159822-09-9 C9H6BrN3
2-Bromo-6-(hydroxy)pyridine-3,4,5-d3 2-Bromo-6-(hydroxy)pyridine-3,4,5-d3 1643543-93-4 C5H4BrNO
2-Bromo-6-(sec-butyl)pyridine 2-Bromo-6-(sec-butyl)pyridine 1142196-91-5 C9H12BrN
2-Bromol-4-amino-5-(3-pyridyl)pyrimidine 2-Bromol-4-amino-5-(3-pyridyl)pyrimidine 1381938-79-9 C9H7BrN4
2-Chloro-4-(2-fluorophenyl)-6-(2-thienyl)-1,3,5-triazine 2-Chloro-4-(2-fluorophenyl)-6-(2-thienyl)-1,3,5-triazine 1227960-27-1 C13H7ClFN3S
2-Chloro-4-(2-methoxyphenyl)-6-methoxy-1,3,5-triazine 2-Chloro-4-(2-methoxyphenyl)-6-methoxy-1,3,5-triazine 1303967-78-3 C11H10ClN3O2
2-Chloro-4-(3-fluorophenyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(3-fluorophenyl)-6-hydroxy-1,3,5-triazine 1303967-48-7 C9H5ClFN3O
2-Chloro-4-(3-methoxyphenyl)-6-methoxy-1,3,5-triazine 2-Chloro-4-(3-methoxyphenyl)-6-methoxy-1,3,5-triazine 1303967-38-5 C11H10ClN3O2
2-Chloro-4-(4-methoxyphenyl)-6-methoxy-1,3,5-triazine 2-Chloro-4-(4-methoxyphenyl)-6-methoxy-1,3,5-triazine 1303967-73-8 C11H10ClN3O2
2-Chloro-4-(4-tolyl)-6-hydroxy-1,3,5-triazine 2-Chloro-4-(4-tolyl)-6-hydroxy-1,3,5-triazine 1303967-50-1 C10H8ClN3O
2-Chloro-4-amino-3-(2-fluorophenyl)pyridine 2-Chloro-4-amino-3-(2-fluorophenyl)pyridine 1381942-64-8 C11H8ClFN2
2-CHLORO-4-AMINO-3-(3-TRIFLUOROMETHYLPHENYL)PYRIDINE 2-CHLORO-4-AMINO-3-(3-TRIFLUOROMETHYLPHENYL)PYRIDINE 1381936-91-9 C12H8ClF3N2
2-Chloro-4-amino-3-(4-methoxyphenyl)pyridine 2-Chloro-4-amino-3-(4-methoxyphenyl)pyridine 1381936-17-9 C12H11ClN2O
2-Chloro-4-amino-5-(2-tolyl)pyridine 2-Chloro-4-amino-5-(2-tolyl)pyridine 1381934-71-9 C12H11ClN2
2-Chloro-4-amino-5-(3-methoxyphenyl)pyridine 2-Chloro-4-amino-5-(3-methoxyphenyl)pyridine 1381942-31-9 C12H11ClN2O
2-Chloro-4-amino-6-(4-fluorophenyl)pyrimidine 2-Chloro-4-amino-6-(4-fluorophenyl)pyrimidine 1353856-21-9 C10H7ClFN3
2-Chloro-4-amino-6-(cyclohexyl)pyrimidine 2-Chloro-4-amino-6-(cyclohexyl)pyrimidine 1353857-11-0 C10H14ClN3
2-Chloro-4-bromo-6-(3-fluorophenyl)pyrimidine 2-Chloro-4-bromo-6-(3-fluorophenyl)pyrimidine 1412959-97-7 C10H5BrClFN2
2-Chloro-4-bromo-6-(3-tolyl)pyrimidine 2-Chloro-4-bromo-6-(3-tolyl)pyrimidine 1412954-39-2 C11H8BrClN2
2-Chloro-4-bromo-6-(cyclopentyl)pyrimidine 2-Chloro-4-bromo-6-(cyclopentyl)pyrimidine 1412957-29-9 C9H10BrClN2
2-Chloro-4-bromo-6-(n-propyl)pyrimidine 2-Chloro-4-bromo-6-(n-propyl)pyrimidine 1412960-22-5 C7H8BrClN2
2-Chloro-4-cyclopropyl-6-hydroxy-1,3,5-triazine 2-Chloro-4-cyclopropyl-6-hydroxy-1,3,5-triazine 1303967-67-0 C6H6ClN3O
2-Chloro-4-methyl-6-hydroxy-1,3,5-triazine 2-Chloro-4-methyl-6-hydroxy-1,3,5-triazine 1303967-52-3 C4H4ClN3O
2-CHLORO-5-(2-TRIFLUOROMETHYLPHENYL)PYRIMIDINE 2-CHLORO-5-(2-TRIFLUOROMETHYLPHENYL)PYRIMIDINE 1261576-21-9 C11H6ClF3N2
2-Chloro-5-(3-methyl-1H-pyrazol-1-yl)pyrimidine 2-Chloro-5-(3-methyl-1H-pyrazol-1-yl)pyrimidine 1363253-89-7 C8H7ClN4
2-Chloro-5-(cyclopentyl)thiazole 2-Chloro-5-(cyclopentyl)thiazole 1412959-68-2 C8H10ClNS
2-Chloro-5-(tetrahydrofuran-3-yl)pyrimidine 2-Chloro-5-(tetrahydrofuran-3-yl)pyrimidine 1363254-20-9 C8H9ClN2O
2-Cyclopentyl-3,4,5-tribromopyridine 2-Cyclopentyl-3,4,5-tribromopyridine 1399480-44-4 C10H10Br3N
2-Cyclopropyl-3,4,5-tribromopyridine 2-Cyclopropyl-3,4,5-tribromopyridine 1399481-74-3 C8H6Br3N
2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 2241870-40-4 C11H15BFNO2
2-Hydroxy-4-(2-cyclopropylpyrimidyl-5-yl)thiazole 2-Hydroxy-4-(2-cyclopropylpyrimidyl-5-yl)thiazole 1215071-60-5 C10H9N3OS
2-Hydroxy-4-(3,5-difluorophenyl)thiazole 2-Hydroxy-4-(3,5-difluorophenyl)thiazole 1188049-01-5 C9H5F2NOS
2-Hydroxy-4-(5-pyrimidyl)thiazole 2-Hydroxy-4-(5-pyrimidyl)thiazole 1215072-18-6 C7H5N3OS
2-Hydroxy-4-(cyclopentyl)thiophene 2-Hydroxy-4-(cyclopentyl)thiophene 1243839-18-0 C9H12OS
2-Hydroxy-5-(2-cyclopropylpyrimidyl-5-yl)thiazole 2-Hydroxy-5-(2-cyclopropylpyrimidyl-5-yl)thiazole 1215073-57-6 C10H9N3OS
2-Hydroxy-5-(2-furyl)pyridine 2-Hydroxy-5-(2-furyl)pyridine 1111106-28-5 C9H7NO2
2-Hydroxy-5-(2-thienyl)thiazole 2-Hydroxy-5-(2-thienyl)thiazole 1215072-47-1 C7H5NOS2
2-Hydroxy-5-(2-trifluoromethylphenyl)pyrimidine 2-Hydroxy-5-(2-trifluoromethylphenyl)pyrimidine 1111104-00-7 C11H7F3N2O
2-Hydroxy-5-(3-furyl)thiazole 2-Hydroxy-5-(3-furyl)thiazole 1215072-84-6 C7H5NO2S
2-Hydroxy-5-(4-chlorophenyl)pyrimidine 2-Hydroxy-5-(4-chlorophenyl)pyrimidine 27956-39-4 C10H7ClN2O
2-Hydroxy-5-(4-fluorophenyl)pyrimidine 2-Hydroxy-5-(4-fluorophenyl)pyrimidine 75175-33-6 C10H7FN2O
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