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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-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256706-09-7 C15H20BN3O2
2-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2256706-19-9 C15H20BN3O2
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(thiophen-3-yl)pyridine-3,4,5-d3 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(thiophen-3-yl)pyridine-3,4,5-d3 2241866-70-4 C15H15BD3NO2S
2-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-4,5,6-d3 2-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-4,5,6-d3 2256706-66-6 C14H17BBrN3O2
2-(4-bromo-2-(methyl-d3)-1H-imidazol-1-yl-5-d)pyridine-3,4,5,6-d4 2-(4-bromo-2-(methyl-d3)-1H-imidazol-1-yl-5-d)pyridine-3,4,5,6-d4 2256710-08-2 C9H8BrN3
2-(4-Methoxyphenyl)-4-hydroxythiazole 2-(4-Methoxyphenyl)-4-hydroxythiazole 1159820-17-3 C10H9NO2S
2-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDIN-4-AMINE 2-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDIN-4-AMINE 1248222-76-5 C9H10N4
2-(Cyclopropyl)-4-hydroxythiazole 2-(Cyclopropyl)-4-hydroxythiazole 1159816-86-0 C6H7NOS
2-(iso-Propyl)-5-hydroxythiazole 2-(iso-Propyl)-5-hydroxythiazole 1159819-94-9 C6H9NOS
2-(methyl-13C)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2-(methyl-13C)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2223052-42-2 C11H17BN2O2
2-(methyl-d3)-1-(pyridin-2-yl-d4)-1H-imidazol-5-d-4-amine 2-(methyl-d3)-1-(pyridin-2-yl-d4)-1H-imidazol-5-d-4-amine 2256707-73-8 C9H10N4
2-(methyl-d3)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,5-d3 2-(methyl-d3)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,5-d3 2241866-74-8 C12H18BNO2
2-(piperidin-1-yl-d10)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-4,6-d2 2-(piperidin-1-yl-d10)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-4,6-d2 2241866-07-7 C15H24BN3O2
2-(propan-2-yl-d7)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2-(propan-2-yl-d7)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2241875-36-3 C14H22BNO2
2-(tert-butoxy)-6-(1H-imidazol-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(tert-butoxy)-6-(1H-imidazol-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256755-16-3 C18H26BN3O3
2-(tert-butoxy)-6-(oxetan-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(tert-butoxy)-6-(oxetan-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256754-83-1 C18H28BNO4
2-(tert-butoxy)-6-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(tert-butoxy)-6-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256755-24-3 C17H28BNO3
2-(tert-butoxy)-6-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(tert-butoxy)-6-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256754-68-2 C18H30BNO3
2-(TETRAHYDROPYRAN-3-YL)-PYRIDINE 2-(TETRAHYDROPYRAN-3-YL)-PYRIDINE 1434127-22-6 C10H13NO
2,3-Dibromo-4-(2-furyl)pyridine 2,3-Dibromo-4-(2-furyl)pyridine 1381937-88-7 C9H5Br2NO
2,3-Dibromo-4-(3-methylpiperidin-1-yl)pyridine 2,3-Dibromo-4-(3-methylpiperidin-1-yl)pyridine 1381943-61-8 C11H14Br2N2
2,3-Dibromo-4-(4-chlorophenyl)pyridine 2,3-Dibromo-4-(4-chlorophenyl)pyridine 1381933-92-1 C11H6Br2ClN
2,3-Dibromo-4-(cyclopropyl)pyridine 2,3-Dibromo-4-(cyclopropyl)pyridine 1381935-40-5 C8H7Br2N
2,3-dibromo-4-(methyl-d3)pyridine 2,3-dibromo-4-(methyl-d3)pyridine 2294957-48-3 C6H5Br2N
2,3-Dibromo-5-(3-chlorophenyl)pyridine 2,3-Dibromo-5-(3-chlorophenyl)pyridine 1399481-41-4 C11H6Br2ClN
2,3-Dibromo-5-(4-chlorophenyl)pyridine 2,3-Dibromo-5-(4-chlorophenyl)pyridine 866930-17-8 C11H6Br2ClN
2,4-bis(methyl-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2,4-bis(methyl-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2241870-60-8 C12H19BN2O2
2,4-Dibromo-3-(4-trifluoromethylphenyl)pyridine 2,4-Dibromo-3-(4-trifluoromethylphenyl)pyridine 1381943-51-6 C12H6Br2F3N
2,4-Dibromo-3-(iso-propyl)pyridine 2,4-Dibromo-3-(iso-propyl)pyridine 1381935-77-8 C8H9Br2N
2,4-Dibromo-6-(2-tolyl)-1,3,5-triazine 2,4-Dibromo-6-(2-tolyl)-1,3,5-triazine 1374664-98-8 C10H7Br2N3
2,4-Dibromo-6-(3-furyl)-1,3,5-triazine 2,4-Dibromo-6-(3-furyl)-1,3,5-triazine 1374665-51-6 C7H3Br2N3O
2,4-Dibromo-6-methyl-1,3,5-triazine 2,4-Dibromo-6-methyl-1,3,5-triazine 1262332-69-3 C4H3Br2N3
2,4-Dichloro-6-(4-cyclopropyl-2-thienyl)-1,3,5-triazine 2,4-Dichloro-6-(4-cyclopropyl-2-thienyl)-1,3,5-triazine 1227958-93-1 C10H7Cl2N3S
2,4-Dichloro-6-(4-tolyl)-1,3,5-triazine 2,4-Dichloro-6-(4-tolyl)-1,3,5-triazine 53815-25-1 C10H7Cl2N3
2,4-Dichloro-6-cyclohexyl-1,3,5-triazine 2,4-Dichloro-6-cyclohexyl-1,3,5-triazine 17419-41-9 C9H11Cl2N3
2,5-Dibromo-4-(3-tolyl)thiazole 2,5-Dibromo-4-(3-tolyl)thiazole 1357580-38-1 C10H7Br2NS
2,5-Dibromo-4-(4-trifluoromethylphenyl)thiazole 2,5-Dibromo-4-(4-trifluoromethylphenyl)thiazole 1357580-43-8 C10H4Br2F3NS
2-Amino-3,5-dibromo-4-(3-methoxyphenyl)pyridine 2-Amino-3,5-dibromo-4-(3-methoxyphenyl)pyridine 1563533-09-4 C12H10Br2N2O
2-Amino-3-bromo-4-(2-chlorophenyl)pyridine 2-Amino-3-bromo-4-(2-chlorophenyl)pyridine 1381941-40-7 C11H8BrClN2
2-Amino-3-bromo-4-(2-methylimidazol-1-yl)pyridine 2-Amino-3-bromo-4-(2-methylimidazol-1-yl)pyridine 1381934-34-4 C9H9BrN4
2-Amino-3-bromo-4-(3-tolyl)pyridine 2-Amino-3-bromo-4-(3-tolyl)pyridine 1381934-04-8 C12H11BrN2
2-Amino-3-bromo-4-(4-methyl-1H-pyrazol-1-yl)pyridine 2-Amino-3-bromo-4-(4-methyl-1H-pyrazol-1-yl)pyridine 1381943-06-1 C9H9BrN4
2-Amino-3-bromo-4-(piperidino)pyridine 2-Amino-3-bromo-4-(piperidino)pyridine 1381938-36-8 C10H14BrN3
2-Amino-4-(2-methoxyphenyl)thiophene 2-Amino-4-(2-methoxyphenyl)thiophene 1159819-72-3 C11H11NOS
2-Amino-4-(2-methylpyrimidyl-5-yl)thiazole 2-Amino-4-(2-methylpyrimidyl-5-yl)thiazole 1215072-73-3 C8H8N4S
2-AMINO-4-(5-PYRIMIDYL)PYRIDINE 2-AMINO-4-(5-PYRIMIDYL)PYRIDINE 1159816-72-4 C9H8N4
2-Amino-4-(morpholino)thiazole 2-Amino-4-(morpholino)thiazole 192332-32-4 C7H11N3OS
2-Amino-4-bromo-3-(3-methoxyphenyl)pyridine 2-Amino-4-bromo-3-(3-methoxyphenyl)pyridine 1381943-55-0 C12H11BrN2O
2-Amino-4-bromo-3-(n-propyl)pyridine 2-Amino-4-bromo-3-(n-propyl)pyridine 1381943-00-5 C8H11BrN2
2-Amino-4-chloro-3-(3-methoxyphenyl)pyridine 2-Amino-4-chloro-3-(3-methoxyphenyl)pyridine 1381934-35-5 C12H11ClN2O
2-Amino-4-chloro-6-(2-fluorophenyl)-1,3,5-triazine 2-Amino-4-chloro-6-(2-fluorophenyl)-1,3,5-triazine 1303967-40-9 C9H6ClFN4
2-Amino-4-chloro-6-(3-pyridyl)-1,3,5-triazine 2-Amino-4-chloro-6-(3-pyridyl)-1,3,5-triazine 1303967-22-7 C8H6ClN5
2-Amino-4-chloro-6-(3-tolyl)pyrimidine 2-Amino-4-chloro-6-(3-tolyl)pyrimidine 862168-09-0 C11H10ClN3
2-Amino-4-ethylfuran 2-Amino-4-ethylfuran 1159819-89-2 C6H9NO
2-Amino-5-(1H-pyridin-2-one)pyridine 2-Amino-5-(1H-pyridin-2-one)pyridine 536747-63-4 C10H9N3O
2-Amino-5-(2-aminopyrimidyl-5-yl)thiazole 2-Amino-5-(2-aminopyrimidyl-5-yl)thiazole 1215072-23-3 C7H7N5S
2-Amino-5-(3-hydroxyphenyl)pyridine 2-Amino-5-(3-hydroxyphenyl)pyridine 1159819-51-8 C11H10N2O
2-Amino-5-(4-pyridyl)pyrimidine 2-Amino-5-(4-pyridyl)pyrimidine 96817-88-8 C9H8N4
2-AMINO-5-(5-THIAZOLYL)PYRIDINE 2-AMINO-5-(5-THIAZOLYL)PYRIDINE 1177269-09-8 C8H7N3S
2-Amino-6-(5-methyl-2-pyridyl)pyrazine 2-Amino-6-(5-methyl-2-pyridyl)pyrazine 1159819-96-1 C10H10N4
2-BROMO-3-(3-BROMOPHENYL)PYRIDINE 2-BROMO-3-(3-BROMOPHENYL)PYRIDINE 1563531-92-9 C11H7Br2N
2-bromo-3-(methyl-d3)pyridine 2-bromo-3-(methyl-d3)pyridine 2259316-05-5 C6H3BrD3N
2-BROMO-3-(PIPERIDIN-3-YL)PYRIDINE 2-BROMO-3-(PIPERIDIN-3-YL)PYRIDINE 1260897-32-2 C10H13BrN2
2-Bromo-4-(2-cyclobutylpyrimidyl-5-yl)thiazole 2-Bromo-4-(2-cyclobutylpyrimidyl-5-yl)thiazole 1215073-77-0 C11H10BrN3S
2-Bromo-4-(2-fluorophenyl)thiophene 2-Bromo-4-(2-fluorophenyl)thiophene 1159819-66-5 C10H6BrFS
2-BROMO-4-(2-TETRAHYDROPYRANYL)PYRIMIDINE 2-BROMO-4-(2-TETRAHYDROPYRANYL)PYRIMIDINE 1622834-17-6 C9H11BrN2O
2-Bromo-4-(2-tollyl)thiazole 2-Bromo-4-(2-tollyl)thiazole 1188124-36-8 C10H8BrNS
2-Bromo-4-(3-furyl)pyridine 2-Bromo-4-(3-furyl)pyridine 1142197-09-8 C9H6BrNO
2-Bromo-4-(3-tolyl)thiophene 2-Bromo-4-(3-tolyl)thiophene 1159820-40-2 C11H9BrS
2-Bromo-4-(5-pyrimidyl)thiazole 2-Bromo-4-(5-pyrimidyl)thiazole 1215073-66-7 C7H4BrN3S
2-Bromo-4-(diethylamino)pyridine 2-Bromo-4-(diethylamino)pyridine 1142194-67-9 C9H13BrN2
2-bromo-4-(methoxy-d3)pyrimidine-5,6-d2 2-bromo-4-(methoxy-d3)pyrimidine-5,6-d2 2256707-53-4 C5H5BrN2O
2-Bromo-4-(sec-butyl)pyridine 2-Bromo-4-(sec-butyl)pyridine 98949-95-2 C9H12BrN
2-Bromo-4-amino-5-(2-trifluoromethylphenyl)pyridine 2-Bromo-4-amino-5-(2-trifluoromethylphenyl)pyridine 1381942-06-8 C12H8BrF3N2
2-Bromo-4-amino-5-(3-pyridyl)pyridine 2-Bromo-4-amino-5-(3-pyridyl)pyridine 1381935-51-8 C10H8BrN3
2-Bromo-4-chloro-6-(2-pyridyl)pyrimidine 2-Bromo-4-chloro-6-(2-pyridyl)pyrimidine 1434127-96-4 C9H5BrClN3
2-Bromo-4-chloro-6-(piperidin-4-yl)pyrimidine 2-Bromo-4-chloro-6-(piperidin-4-yl)pyrimidine 1434127-88-4 C9H11BrClN3
2-BROMO-5-(1-HYDROXY-1-ETHYLETHYL)PYRIMIDINE 2-BROMO-5-(1-HYDROXY-1-ETHYLETHYL)PYRIMIDINE 1434128-11-6 C8H11BrN2O
2-Bromo-5-(2-hydroxypiperidino)pyridine 2-Bromo-5-(2-hydroxypiperidino)pyridine 1314353-67-7 C10H13BrN2O
2-Bromo-5-(2-methoxyphenyl)thiazole 2-Bromo-5-(2-methoxyphenyl)thiazole 1215072-35-7 C10H8BrNOS
2-Bromo-5-(2-thienyl)thiazole 2-Bromo-5-(2-thienyl)thiazole 1215074-11-5 C7H4BrNS2
2-Bromo-5-(2-tolyl)thiophene 2-Bromo-5-(2-tolyl)thiophene 1159818-14-0 C11H9BrS
2-Bromo-5-(3-fluorolphenyl)thiazole 2-Bromo-5-(3-fluorolphenyl)thiazole 1215071-68-3 C9H5BrFNS
2-Bromo-5-(3-pyridyl)pyrimidine 2-Bromo-5-(3-pyridyl)pyrimidine 1353856-22-0 C9H6BrN3
2-Bromo-5-(3-thienyl)thiazole 2-Bromo-5-(3-thienyl)thiazole 1215072-46-0 C7H4BrNS2
2-Bromo-5-(4-methoxyphenyl)pyridine 2-Bromo-5-(4-methoxyphenyl)pyridine 608517-43-7 C12H10BrNO
2-Bromo-5-(4-trifluoromethylphenyl)pyrimidine 2-Bromo-5-(4-trifluoromethylphenyl)pyrimidine 1353857-03-0 C11H6BrF3N2
2-Bromo-5-(cyclobutyl)furan 2-Bromo-5-(cyclobutyl)furan 1159817-08-9 C8H9BrO
2-Bromo-5-(pyrazol-4-yl)pyridine 2-Bromo-5-(pyrazol-4-yl)pyridine 1346536-56-8 C8H6BrN3
2-Bromo-5-(thiazol-5-yl)pyridine 2-Bromo-5-(thiazol-5-yl)pyridine 1563532-41-1 C8H5BrN2S
2-Bromo-5-amino-4-(3-chlorophenyl)pyridine 2-Bromo-5-amino-4-(3-chlorophenyl)pyridine 1381935-03-0 C11H8BrClN2
2-Bromo-5-amino-4-(3-methyl-1H-pyrazol-1-yl)pyridine 2-Bromo-5-amino-4-(3-methyl-1H-pyrazol-1-yl)pyridine 1381934-78-6 C9H9BrN4
2-Bromo-5-amino-4-(5-pyrimidyl)pyridine 2-Bromo-5-amino-4-(5-pyrimidyl)pyridine 1381942-45-5 C9H7BrN4
2-Bromo-5-amino-4-(imidazol-1-yl)pyridine 2-Bromo-5-amino-4-(imidazol-1-yl)pyridine 1381935-76-7 C8H7BrN4
2-Bromo-5-morpholinothiazole 2-Bromo-5-morpholinothiazole 566159-21-5 C7H9BrN2OS
2-Bromo-6-(2-methoxyphenyl)pyridine 2-Bromo-6-(2-methoxyphenyl)pyridine 1142196-80-2 C12H10BrNO
2-Bromo-6-(3-methoxyphenyl)pyridine 2-Bromo-6-(3-methoxyphenyl)pyridine 851595-28-3 C12H10BrNO
2-Bromo-6-(4-fluorophenyl)pyridine 2-Bromo-6-(4-fluorophenyl)pyridine 1142196-75-5 C11H7BrFN
2-Bromol-4-amino-5-(2-furyl)pyrimidine 2-Bromol-4-amino-5-(2-furyl)pyrimidine 1381944-18-8 C8H6BrN3O
2-Chloro-3-(oxan-2-yl)pyridine 2-Chloro-3-(oxan-2-yl)pyridine 1622836-00-3 C10H12ClNO
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