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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
3-BROMO-4-(OXOLAN-3-YLOXY)PYRIDINE 3-BROMO-4-(OXOLAN-3-YLOXY)PYRIDINE 1289111-37-0 C9H10BrNO2
3-Bromo-5-(2-methyl-4-fluorophenyl)pyridine 3-Bromo-5-(2-methyl-4-fluorophenyl)pyridine 1314356-75-6 C12H9BrFN
3-BROMO-5-(3-BROMOPHENYL)PYRIDINE 3-BROMO-5-(3-BROMOPHENYL)PYRIDINE 1378866-78-4 C11H7Br2N
3-Bromo-5-(4-tetrahydropyranyl)pyridine 3-Bromo-5-(4-tetrahydropyranyl)pyridine 1399480-56-8 C10H12BrNO
3-Bromo-5-(cyclopentyl)pyridine 3-Bromo-5-(cyclopentyl)pyridine 1209459-84-6 C10H12BrN
3-Bromo-5-(pyrazin-2-yl)pyridine 3-Bromo-5-(pyrazin-2-yl)pyridine 1412960-42-9 C9H6BrN3
3-bromo-6-(tetrahydrofuran-2-yl)pyridazine 3-bromo-6-(tetrahydrofuran-2-yl)pyridazine 2222934-87-2 C8H9BrN2O
3-BROMO-N,N-DIETHYLPYRIDIN-2-AMINE 3-BROMO-N,N-DIETHYLPYRIDIN-2-AMINE 1248729-13-6 C9H13BrN2
3-chloro-6-(1,4-dioxan-2-yl)pyridazine 3-chloro-6-(1,4-dioxan-2-yl)pyridazine 2222933-98-2 C8H9ClN2O2
3-CHLORO-6-(PIPERIDIN-3-YL)PYRIDAZINE 3-CHLORO-6-(PIPERIDIN-3-YL)PYRIDAZINE 1622834-32-5 C9H12ClN3
3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 2241874-94-0 C11H15BFNO2
3-Hydroxy-2-(3-tolyl)pyridine 3-Hydroxy-2-(3-tolyl)pyridine 1261940-34-4 C12H11NO
3-Hydroxy-2-(4-methoxyphenyl)pyridine 3-Hydroxy-2-(4-methoxyphenyl)pyridine 36726-85-9 C12H11NO2
3-Hydroxy-5-(2-furyl)pyridine 3-Hydroxy-5-(2-furyl)pyridine 1261971-03-2 C9H7NO2
3-Hydroxy-5-(2-pyridyl)pyridine 3-Hydroxy-5-(2-pyridyl)pyridine 1314356-79-0 C10H8N2O
3-Hydroxy-5-(4-aminophenyl)pyridine 3-Hydroxy-5-(4-aminophenyl)pyridine 1258611-14-1 C11H10N2O
3-Hydroxy-5-(4-methylimidazol-1-yl)pyridine 3-Hydroxy-5-(4-methylimidazol-1-yl)pyridine 1314356-87-0 C9H9N3O
3-Hydroxy-5-(iso-propyl)pyridine 3-Hydroxy-5-(iso-propyl)pyridine 1243280-48-9 C8H11NO
3-Hydroxy-5-(piperidino)pyridine 3-Hydroxy-5-(piperidino)pyridine 226084-35-1 C10H14N2O
4-(1H-imidazol-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(1H-imidazol-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256755-61-8 C14H18BN3O2
4-(2-bromo-5-cyclopropylphenyl)morpholine 4-(2-bromo-5-cyclopropylphenyl)morpholine 2222934-31-6 C13H16BrNO
4-(2-METHYL-1H-IMIDAZOL-1-YL)PYRIDIN-2-AMINE 4-(2-METHYL-1H-IMIDAZOL-1-YL)PYRIDIN-2-AMINE 1314356-15-4 C9H10N4
4-(3-Pyridyl)thiazole 4-(3-Pyridyl)thiazole 162704-76-9 C8H6N2S
4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl-2,5-d2)pyridine-2,3,5,6-d4 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl-2,5-d2)pyridine-2,3,5,6-d4 2256710-47-9 C14H18BN3O2
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(m-tolyl)-1H-1,2,3-triazole 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(m-tolyl)-1H-1,2,3-triazole 2256756-24-6 C15H20BN3O2
4-(4-bromo-1H-imidazol-1-yl-2,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(4-bromo-1H-imidazol-1-yl-2,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256706-67-7 C14H17BBrN3O2
4-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-2-(methyl-d3)pyridine-3,5,6-d3 4-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-2-(methyl-d3)pyridine-3,5,6-d3 2256709-90-5 C9H8BrN3
4-(4-bromophenyl)pyrimidine-2,5,6-d3 4-(4-bromophenyl)pyrimidine-2,5,6-d3 2256712-12-4 C10H4BrD3N2
4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl-3,4,6-d3)morpholine-2,2,3,3,5,5,6,6-d8 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl-3,4,6-d3)morpholine-2,2,3,3,5,5,6,6-d8 2241875-44-3 C15H23BN2O3
4-(FURAN-3-YL)PYRIDIN-2-AMINE 4-(FURAN-3-YL)PYRIDIN-2-AMINE 1159820-84-4 C9H8N2O
4-(methyl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 4-(methyl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 2241874-76-8 C12H18BNO2
4-(methyl-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2,6-d2 4-(methyl-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2,6-d2 2241865-91-6 C11H17BN2O2
4-(tetrahydro-2H-pyran-2-yl)pyridin-2-amine 4-(tetrahydro-2H-pyran-2-yl)pyridin-2-amine 1622834-66-5 C10H14N2O
4-(tetrahydrofuran-2-yl)pyrimidin-2-ol 4-(tetrahydrofuran-2-yl)pyrimidin-2-ol 1850338-49-6 C8H10N2O2
4,5-Dibromo-2-(2-trifluoromethylphenyl)thiazole 4,5-Dibromo-2-(2-trifluoromethylphenyl)thiazole 1314354-43-2 C10H4Br2F3NS
4,5-Dibromo-2-(4-tolyl)thiazole 4,5-Dibromo-2-(4-tolyl)thiazole 1314355-88-8 C10H7Br2NS
4,5-Dibromo-2-(sec-butyl)thiazole 4,5-Dibromo-2-(sec-butyl)thiazole 1643577-16-5 C7H9Br2NS
4,5-Dibromo-2-hydroxythiazole 4,5-Dibromo-2-hydroxythiazole 1314357-15-7 C3HBr2NOS
4,6-dichloropyrimidine-2,5-d2 4,6-dichloropyrimidine-2,5-d2 2259315-68-7 C4H2Cl2N2
4-Amino-1-(3-fluorophenyl)imidazole 4-Amino-1-(3-fluorophenyl)imidazole 1185762-04-2 C9H8FN3
4-Amino-2-(2-furyl)thiazole 4-Amino-2-(2-furyl)thiazole 123970-77-4 C7H6N2OS
4-Amino-2-(3,5-difluorophenyl)thiazole 4-Amino-2-(3,5-difluorophenyl)thiazole 1159814-78-4 C9H6F2N2S
4-Amino-2-(3-tolyl)pyrimidine 4-Amino-2-(3-tolyl)pyrimidine 1250100-53-8 C11H11N3
4-Amino-2-(4-aminophenyl)pyridine 4-Amino-2-(4-aminophenyl)pyridine 1215073-26-9 C11H11N3
4-Amino-2-(4-trifluoromethylphenyl)thiazole 4-Amino-2-(4-trifluoromethylphenyl)thiazole 1159816-93-9 C10H7F3N2S
4-Amino-2-chloro-3-bromo-5-(2-cyanophenyl)pyridine 4-Amino-2-chloro-3-bromo-5-(2-cyanophenyl)pyridine 1563532-76-2 C12H7BrClN3
4-Amino-2-chloro-3-bromo-5-(2-tolyl)pyridine 4-Amino-2-chloro-3-bromo-5-(2-tolyl)pyridine 1563531-44-1 C12H10BrClN2
4-Amino-2-chloro-3-bromo-5-(4-fluorophenyl)pyridine 4-Amino-2-chloro-3-bromo-5-(4-fluorophenyl)pyridine 1563532-30-8 C11H7BrClFN2
4-Amino-2-chloro-3-bromo-5-(cyclopentyl)pyridine 4-Amino-2-chloro-3-bromo-5-(cyclopentyl)pyridine 1563533-99-2 C10H12BrClN2
4-Amino-2-methyl-6-(2-methyl-4-thiazolyl)pyrimidine 4-Amino-2-methyl-6-(2-methyl-4-thiazolyl)pyrimidine 1159818-26-4 C9H10N4S
4-Amino-2-methyl-6-(3-pyridyl)pyrimidine 4-Amino-2-methyl-6-(3-pyridyl)pyrimidine 90916-55-5 C10H10N4
4-AMINO-3-(3,5-DIFLUOROPHENYL)PYRIDINE 4-AMINO-3-(3,5-DIFLUOROPHENYL)PYRIDINE 1343469-25-9 C11H8F2N2
4-Amino-3-(diethylamino)pyridine 4-Amino-3-(diethylamino)pyridine 144864-29-9 C9H15N3
4-Amino-3-(pyrazol-4-yl)pyridine 4-Amino-3-(pyrazol-4-yl)pyridine 1563530-62-0 C8H8N4
4-Amino-3,5-dibromo-2-(2-trifluoromethylphenyl)pyridine 4-Amino-3,5-dibromo-2-(2-trifluoromethylphenyl)pyridine 1563533-55-0 C12H7Br2F3N2
4-Amino-3,5-dibromo-2-(3-fluorophenyl)pyridine 4-Amino-3,5-dibromo-2-(3-fluorophenyl)pyridine 1563533-68-5 C11H7Br2FN2
4-Amino-3,5-dibromo-2-(sec-butyl)pyridine 4-Amino-3,5-dibromo-2-(sec-butyl)pyridine 1563533-96-9 C9H12Br2N2
4-Amino-3-bromo-2-(3-hydroxypiperidin-1-yl)pyridine 4-Amino-3-bromo-2-(3-hydroxypiperidin-1-yl)pyridine 1381942-32-0 C10H14BrN3O
4-Amino-3-bromo-2-(dimethylamino)pyridine 4-Amino-3-bromo-2-(dimethylamino)pyridine 1417618-68-8 C7H10BrN3
4-Amino-3-bromo-6-(3-methoxyphenyl)pyridine 4-Amino-3-bromo-6-(3-methoxyphenyl)pyridine 1381937-48-9 C12H11BrN2O
4-Amino-3-bromo-6-(cyclohexyloxy)pyridine 4-Amino-3-bromo-6-(cyclohexyloxy)pyridine 1446408-36-1 C11H15BrN2O
4-Amino-5-bromo-2-(pyrimidin-5-yl)pyrimidine 4-Amino-5-bromo-2-(pyrimidin-5-yl)pyrimidine 1563531-94-1 C8H6BrN5
4-Amino-5-bromo-2-(thiazol-5-yl)pyrimidine 4-Amino-5-bromo-2-(thiazol-5-yl)pyrimidine 1502859-11-1 C7H5BrN4S
4-Amino-6-(2-pyridyl)pyrimidine 4-Amino-6-(2-pyridyl)pyrimidine 1159818-72-0 C9H8N4
4-Amino-6-(3-furyl)pyrimidine 4-Amino-6-(3-furyl)pyrimidine 1159820-07-1 C8H7N3O
4-Amino-6-(piperidin-3-yl)pyrimidine 4-Amino-6-(piperidin-3-yl)pyrimidine 1556045-94-3 C9H14N4
4-Amino-6-methyl-2-(3-pyridyl)pyrimidine 4-Amino-6-methyl-2-(3-pyridyl)pyrimidine 1159818-82-2 C10H10N4
4-Bromo-1-(2-amino-3-bromo-4-pyridyl)imidazole 4-Bromo-1-(2-amino-3-bromo-4-pyridyl)imidazole 1357580-28-9 C8H6Br2N4
4-Bromo-1-(2-methoxy-4-pyridyl)imidazole 4-Bromo-1-(2-methoxy-4-pyridyl)imidazole 1353856-23-1 C9H8BrN3O
4-Bromo-1-(5-cyclopropyl-3-pyridyl)pyrazole 4-Bromo-1-(5-cyclopropyl-3-pyridyl)pyrazole 1353857-08-5 C11H10BrN3
4-Bromo-2-(2-amino-5-pyrimidyl)pyridine 4-Bromo-2-(2-amino-5-pyrimidyl)pyridine 1159815-05-0 C9H7BrN4
4-Bromo-2-(2-chlorophenyl)thiazole 4-Bromo-2-(2-chlorophenyl)thiazole 1353856-36-6 C9H5BrClNS
4-bromo-2-(3-bromophenyl)pyridine-3,5,6-d3 4-bromo-2-(3-bromophenyl)pyridine-3,5,6-d3 2256711-90-5 C11H7Br2N
4-Bromo-2-(3-tetrahydropyranyl)pyridine 4-Bromo-2-(3-tetrahydropyranyl)pyridine 1353853-98-1 C10H12BrNO
4-BROMO-2-(4-FLUOROPHENYL)-PYRIDINE 4-BROMO-2-(4-FLUOROPHENYL)-PYRIDINE 916824-57-2 C11H7BrFN
4-Bromo-2-(4-methyl-1H-pyrazol-1-yl)pyridine 4-Bromo-2-(4-methyl-1H-pyrazol-1-yl)pyridine 1159814-82-0 C9H8BrN3
4-Bromo-2-(cyclohexyl)pyridine 4-Bromo-2-(cyclohexyl)pyridine 1142194-12-4 C11H14BrN
4-Bromo-2-(pyrrolidin-3-yl)thiazole 4-Bromo-2-(pyrrolidin-3-yl)thiazole 1159815-45-8 C7H9BrN2S
4-bromo-2-chloro-3-iodopyridine-5,6-d2 4-bromo-2-chloro-3-iodopyridine-5,6-d2 2294949-48-5 C5H2BrClIN
4-bromo-2-fluoro-6-(methyl-d3)pyridine-3,5-d2 4-bromo-2-fluoro-6-(methyl-d3)pyridine-3,5-d2 2294957-80-3 C6H5BrFN
4-BROMO-3-(1H-PYRAZOL-1-YL)PYRIDINE 4-BROMO-3-(1H-PYRAZOL-1-YL)PYRIDINE 1563532-47-7 C8H6BrN3
4-Bromo-3-(2-bromophenyl)pyridine 4-Bromo-3-(2-bromophenyl)pyridine 1418918-54-3 C11H7Br2N
4-BROMO-3-(3-METHYLPIPERIDIN-1-YL)PYRIDINE 4-BROMO-3-(3-METHYLPIPERIDIN-1-YL)PYRIDINE 1563533-14-1 C11H15BrN2
4-Bromo-3-(4-trifluoromethylphenyl)pyridine 4-Bromo-3-(4-trifluoromethylphenyl)pyridine 1374665-96-9 C12H7BrF3N
4-Bromo-3-amino-6-(1H-pyrrol-1-yl)pyridine 4-Bromo-3-amino-6-(1H-pyrrol-1-yl)pyridine 1381933-83-0 C9H8BrN3
4-Bromo-3-amino-6-(2-methoxyphenyl)pyridine 4-Bromo-3-amino-6-(2-methoxyphenyl)pyridine 1381941-29-2 C12H11BrN2O
4-Bromo-3-amino-6-(3-thienyl)pyridine 4-Bromo-3-amino-6-(3-thienyl)pyridine 1381943-89-0 C9H7BrN2S
4-Bromo-3-amino-6-(4-hydroxypiperidin-1-yl)pyridine 4-Bromo-3-amino-6-(4-hydroxypiperidin-1-yl)pyridine 1381942-11-5 C10H14BrN3O
4-Bromo-3-amino-6-(iso-propyl)pyridine 4-Bromo-3-amino-6-(iso-propyl)pyridine 1381934-26-4 C8H11BrN2
4-Bromo-3-amino-6-(tert-butyl)pyridine 4-Bromo-3-amino-6-(tert-butyl)pyridine 1381934-43-5 C9H13BrN2
4-Bromo-5-(n-propyl)-2-(methylethylamino)thiazole 4-Bromo-5-(n-propyl)-2-(methylethylamino)thiazole 1643542-15-7 C9H15BrN2S
4-Bromo-5-ethylpyrimidine 4-Bromo-5-ethylpyrimidine 1563535-11-4 C6H7BrN2
4-Bromo-5-methyl-2-(methylethylamino)thiazole 4-Bromo-5-methyl-2-(methylethylamino)thiazole 1643543-03-6 C7H11BrN2S
4-Bromo-6-(2-furyl)pyrimidine 4-Bromo-6-(2-furyl)pyrimidine 1086382-27-5 C8H5BrN2O
4-Bromo-6-(4-methylpiperidin-1-yl)pyrimidine 4-Bromo-6-(4-methylpiperidin-1-yl)pyrimidine 1314356-61-0 C10H14BrN3
4-bromopyridin-2,5,6-d3-3-ol 4-bromopyridin-2,5,6-d3-3-ol 2259315-94-9 C5H4BrNO
4-Chloro-2-(4-tetrahydropyranyl)pyridine 4-Chloro-2-(4-tetrahydropyranyl)pyridine 1434127-66-8 C10H12ClNO
4-Chloro-2-(piperidin-4-yl)pyridine 4-Chloro-2-(piperidin-4-yl)pyridine 899357-00-7 C10H13ClN2
4-Chloro-2-methyl-6-(2-methoxyphenyl)pyrimidine 4-Chloro-2-methyl-6-(2-methoxyphenyl)pyrimidine 1159820-94-6 C12H11ClN2O
4-Chloro-2-methyl-6-(3-pyridyl)pyrimidine 4-Chloro-2-methyl-6-(3-pyridyl)pyrimidine 1159817-95-4 C10H8ClN3
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