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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-Hydroxy-4-(piperidin-3-yl)pyridine 2-Hydroxy-4-(piperidin-3-yl)pyridine 1260863-26-0 C10H14N2O
2-Hydroxy-5-(2-amino-5-pyridyl)pyridine 2-Hydroxy-5-(2-amino-5-pyridyl)pyridine 1110657-41-4 C10H9N3O
2-Hydroxy-5-(2-iso-propylpyrimidyl-5-yl)thiazole 2-Hydroxy-5-(2-iso-propylpyrimidyl-5-yl)thiazole 1215073-59-8 C10H11N3OS
2-Hydroxy-5-(2-methylpyrimidyl-5-yl)thiazole 2-Hydroxy-5-(2-methylpyrimidyl-5-yl)thiazole 1215071-66-1 C8H7N3OS
2-Hydroxy-5-(3,5-difluorophenyl)thiazole 2-Hydroxy-5-(3,5-difluorophenyl)thiazole 1215071-77-4 C9H5F2NOS
2-Hydroxy-5-(3-chlorophenyl)pyrimidine 2-Hydroxy-5-(3-chlorophenyl)pyrimidine 74963-17-0 C10H7ClN2O
2-Hydroxy-5-(3-thienyl)pyrimidine 2-Hydroxy-5-(3-thienyl)pyrimidine 1111113-74-6 C8H6N2OS
2-Hydroxy-5-(3-trifluoromethylphenyl)pyridine 2-Hydroxy-5-(3-trifluoromethylphenyl)pyridine 76053-46-8 C12H8F3NO
2-Hydroxy-5-(4-tolyl)thiazole 2-Hydroxy-5-(4-tolyl)thiazole 1215072-44-8 C10H9NOS
2-Hydroxy-5-(cyclopropyl)thiazole 2-Hydroxy-5-(cyclopropyl)thiazole 1215074-15-9 C6H7NOS
2-Hydroxy-5-(n-propyl)thiazole 2-Hydroxy-5-(n-propyl)thiazole 1215072-82-4 C6H9NOS
2-Hydroxy-6-(5-pyrimidyl)pyridine 2-Hydroxy-6-(5-pyrimidyl)pyridine 1111110-39-4 C9H7N3O
3-(2-(methyl-d3)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl-5-d)pyridine-2,4,5,6-d4 3-(2-(methyl-d3)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl-5-d)pyridine-2,4,5,6-d4 2256710-51-5 C15H20BN3O2
3-(3-AMINOPYRIDIN-2-YL)BENZONITRILE 3-(3-AMINOPYRIDIN-2-YL)BENZONITRILE 1553934-38-5 C12H9N3
3-(3-bromophenyl)pyridazine-4,5,6-d3 3-(3-bromophenyl)pyridazine-4,5,6-d3 2256712-34-0 C10H7BrN2
3-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256706-79-1 C15H20BN3O2
3-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 3-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 2256706-45-1 C15H20BN3O2
3-(4-bromo-1H-imidazol-1-yl-2,5-d2)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(4-bromo-1H-imidazol-1-yl-2,5-d2)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256706-73-5 C14H15BBrD2N3O2
3-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256706-56-4 C14H17BBrN3O2
3-(4-TERT-BUTYLPHENYL)PYRIDIN-4-AMINE 3-(4-TERT-BUTYLPHENYL)PYRIDIN-4-AMINE 1368997-43-6 C15H18N2
3-(5-AMINOPYRIDIN-2-YL)BENZONITRILE 3-(5-AMINOPYRIDIN-2-YL)BENZONITRILE 1357165-93-5 C12H9N3
3-(6-BROMOPYRIDIN-2-YL)BENZONITRILE 3-(6-BROMOPYRIDIN-2-YL)BENZONITRILE 1490708-38-7 C12H7BrN2
3-(methoxy-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 3-(methoxy-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,4,6-d3 2241875-00-1 C12H18BNO3
3-(methyl-d3)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-3,5-d2)pyridine-4,5,6-d3 3-(methyl-d3)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-3,5-d2)pyridine-4,5,6-d3 2256706-36-0 C15H12BD8N3O2
3-(SEC-BUTYL)PYRIDIN-4-AMINE 3-(SEC-BUTYL)PYRIDIN-4-AMINE 1374664-46-6 C9H14N2
3-(Thiazol-5-yl)chlorobenzene 3-(Thiazol-5-yl)chlorobenzene 1563531-39-4 C9H6ClNS
3,4-Dibromo-2-(2-methylpiperidin-1-yl)pyridine 3,4-Dibromo-2-(2-methylpiperidin-1-yl)pyridine 1381942-52-4 C11H14Br2N2
3,4-Dibromo-2-(3-chlorophenyl)pyridine 3,4-Dibromo-2-(3-chlorophenyl)pyridine 1381943-42-5 C11H6Br2ClN
3,4-Dibromo-2-(4-methyl-1H-pyrazol-1-yl)pyridine 3,4-Dibromo-2-(4-methyl-1H-pyrazol-1-yl)pyridine 1381943-59-4 C9H7Br2N3
3,4-Dibromo-2-(4-trifluoromethylphenyl)pyridine 3,4-Dibromo-2-(4-trifluoromethylphenyl)pyridine 1381943-48-1 C12H6Br2F3N
3,4-Dibromo-2-(pyrrolidino)pyridine 3,4-Dibromo-2-(pyrrolidino)pyridine 1381934-64-0 C9H10Br2N2
3,4-Dibromo-2-phenylpyridine 3,4-Dibromo-2-phenylpyridine 1381941-37-2 C11H7Br2N
3,4-Dibromo-6-(3-furyl)pyridine 3,4-Dibromo-6-(3-furyl)pyridine 1381942-50-2 C9H5Br2NO
3,4-Dibromo-6-(3-pyridyl)pyridine 3,4-Dibromo-6-(3-pyridyl)pyridine 1381941-95-2 C10H6Br2N2
3,4-Dibromo-6-(imidazol-1-yl)pyridine 3,4-Dibromo-6-(imidazol-1-yl)pyridine 1381942-40-0 C8H5Br2N3
3,4-Dibromo-6-(pyrrolidino)pyridine 3,4-Dibromo-6-(pyrrolidino)pyridine 1381943-86-7 C9H10Br2N2
3,5-Dibromo-6-(3-chlorophenyl)pyridine 3,5-Dibromo-6-(3-chlorophenyl)pyridine 1399482-08-6 C11H6Br2ClN
3-AMINO-2-CYCLOPENTYLPYRIDINE 3-AMINO-2-CYCLOPENTYLPYRIDINE 1417519-40-4 C10H14N2
3-AMINO-4-(2-TETRAHYDROPYRANYL)PYRIDINE 3-AMINO-4-(2-TETRAHYDROPYRANYL)PYRIDINE 1355012-91-7 C10H14N2O
3-Amino-4-(methylethylamino)pyridine 3-Amino-4-(methylethylamino)pyridine 1094890-81-9 C8H13N3
3-AMINO-5-(3-METHYLPIPERIDIN-1-YL)PYRIDINE 3-AMINO-5-(3-METHYLPIPERIDIN-1-YL)PYRIDINE 1314355-50-4 C11H17N3
3-AMINO-5-(4-METHYLPIPERIDIN-1-YL)PYRIDINE 3-AMINO-5-(4-METHYLPIPERIDIN-1-YL)PYRIDINE 1314353-96-2 C11H17N3
3-Amino-5-(N-methylpiperazin-1-yl)pyridine 3-Amino-5-(N-methylpiperazin-1-yl)pyridine 1314355-78-6 C10H16N4
3-Amino-5-bromo-2-cyclopropylpyridine 3-Amino-5-bromo-2-cyclopropylpyridine 1563532-87-5 C8H9BrN2
3-Amino-5-bromo-6-(cyclopropyl)pyridine 3-Amino-5-bromo-6-(cyclopropyl)pyridine 1399480-74-0 C8H9BrN2
3-BROMO-1-(PYRIDAZIN-3-YL)-1H-PYRAZOLE 3-BROMO-1-(PYRIDAZIN-3-YL)-1H-PYRAZOLE 1622843-55-3 C7H5BrN4
3-Bromo-2-(2-aminophenyl)pyridine 3-Bromo-2-(2-aminophenyl)pyridine 1417517-91-9 C11H9BrN2
3-BROMO-2-(2-FLUOROPHENYL)PYRIDIN-4-AMINE 3-BROMO-2-(2-FLUOROPHENYL)PYRIDIN-4-AMINE 1381943-76-5 C11H8BrFN2
3-Bromo-2-(3,5-difluorophenyl)pyridine 3-Bromo-2-(3,5-difluorophenyl)pyridine 1417519-44-8 C11H6BrF2N
3-BROMO-2-(3-FLUOROPHENYL)PYRIDIN-4-AMINE 3-BROMO-2-(3-FLUOROPHENYL)PYRIDIN-4-AMINE 1381935-99-4 C11H8BrFN2
3-Bromo-2-(4-bromophenyl)pyridine 3-Bromo-2-(4-bromophenyl)pyridine 1563529-42-9 C11H7Br2N
3-Bromo-2-(4-fluoro-2-methylphenyl)pyridine 3-Bromo-2-(4-fluoro-2-methylphenyl)pyridine 1417518-67-2 C12H9BrFN
3-BROMO-2-(FURAN-2-YL)PYRIDIN-4-AMINE 3-BROMO-2-(FURAN-2-YL)PYRIDIN-4-AMINE 1381943-69-6 C9H7BrN2O
3-BROMO-2-(MORPHOLIN-4-YL)PYRIDIN-4-AMINE 3-BROMO-2-(MORPHOLIN-4-YL)PYRIDIN-4-AMINE 1381937-06-9 C9H12BrN3O
3-BROMO-2-(THIOPHEN-3-YL)PYRIDIN-4-AMINE 3-BROMO-2-(THIOPHEN-3-YL)PYRIDIN-4-AMINE 1381937-08-1 C9H7BrN2S
3-BROMO-2-[4-(TRIFLUOROMETHYL)PHENYL]PYRIDIN-4-AMINE 3-BROMO-2-[4-(TRIFLUOROMETHYL)PHENYL]PYRIDIN-4-AMINE 1381936-20-4 C12H8BrF3N2
3-Bromo-4-(2,4-difluorophenyl)pyridine 3-Bromo-4-(2,4-difluorophenyl)pyridine 1374665-92-5 C11H6BrF2N
3-Bromo-4-(2-fluorophenyl)pyridine 3-Bromo-4-(2-fluorophenyl)pyridine 1374664-87-5 C11H7BrFN
3-Bromo-4-(3-chlorophenyl)pyridine 3-Bromo-4-(3-chlorophenyl)pyridine 1374665-02-7 C11H7BrClN
3-Bromo-4-(4-tolyl)pyridine 3-Bromo-4-(4-tolyl)pyridine 1246851-82-0 C12H10BrN
3-BROMO-4-AMINO-6-(2-TRIFLUOROMETHYLPHENYL)PYRIDINE 3-BROMO-4-AMINO-6-(2-TRIFLUOROMETHYLPHENYL)PYRIDINE 1381935-29-0 C12H8BrF3N2
3-BROMO-4-CHLORO-5-CYCLOPROPYLPYRIDIN-2-AMINE 3-BROMO-4-CHLORO-5-CYCLOPROPYLPYRIDIN-2-AMINE 1417518-54-7 C8H8BrClN2
3-bromo-5-(1H-imidazol-1-yl-d3)pyridine-2,4,6-d3 3-bromo-5-(1H-imidazol-1-yl-d3)pyridine-2,4,6-d3 2256707-23-8 C8BrD6N3
3-BROMO-5-(2-BROMOPHENYL)PYRIDINE 3-BROMO-5-(2-BROMOPHENYL)PYRIDINE 1563534-95-1 C11H7Br2N
3-Bromo-5-(4-aminophenyl)pyridine 3-Bromo-5-(4-aminophenyl)pyridine 1314355-42-4 C11H9BrN2
3-Bromo-5-(4-methylpiperidin-1-yl)pyridine 3-Bromo-5-(4-methylpiperidin-1-yl)pyridine 1289048-18-5 C11H15BrN2
3-Bromo-6-(2-aminothiazol-4-yl)pyridine 3-Bromo-6-(2-aminothiazol-4-yl)pyridine 1159821-28-9 C8H6BrN3S
3-Bromo-6-(3,4-difluorophenyl)pyridine 3-Bromo-6-(3,4-difluorophenyl)pyridine 142257-00-9 C11H6BrF2N
3-Bromo-6-(piperidin-3-yl)pyridazine 3-Bromo-6-(piperidin-3-yl)pyridazine 1622835-37-3 C9H12BrN3
3-Cyclopropyl-5-(thiazol-5-yl)bromobenzene 3-Cyclopropyl-5-(thiazol-5-yl)bromobenzene 1563532-75-1 C12H10BrNS
3-Hydroxy-2-(3-furyl)pyridine 3-Hydroxy-2-(3-furyl)pyridine 1417519-00-6 C9H7NO2
3-Hydroxy-2,3'-bipyridine 3-Hydroxy-2,3'-bipyridine 380849-23-0 C10H8N2O
3-Hydroxy-5-(2-aminophenyl)pyridine 3-Hydroxy-5-(2-aminophenyl)pyridine 1314356-77-8 C11H10N2O
3-Hydroxy-5-(3-fluorophenyl)pyridine 3-Hydroxy-5-(3-fluorophenyl)pyridine 1214377-86-2 C11H8FNO
3-Hydroxy-5-(3-thienyl)pyridine 3-Hydroxy-5-(3-thienyl)pyridine 1261906-47-1 C9H7NOS
3-Hydroxy-5-(diethylamino)pyridine 3-Hydroxy-5-(diethylamino)pyridine 226084-36-2 C9H14N2O
3-Hydroxy-6-(4-tolyl)pyridine 3-Hydroxy-6-(4-tolyl)pyridine 1262011-31-3 C12H11NO
4-(2-AMINOPHENYL)PYRIDIN-3-AMINE 4-(2-AMINOPHENYL)PYRIDIN-3-AMINE 146141-02-8 C11H11N3
4-(2-bromophenyl)-6-(methyl-d3)pyrimidine-2,5-d2 4-(2-bromophenyl)-6-(methyl-d3)pyrimidine-2,5-d2 2256711-67-6 C11H9BrN2
4-(2-Trifluoromethylphenyl)thiazole 4-(2-Trifluoromethylphenyl)thiazole 383145-68-4 C10H6F3NS
4-(3-AMINOPYRIDIN-4-YL)BENZONITRILE 4-(3-AMINOPYRIDIN-4-YL)BENZONITRILE 1563530-23-3 C12H9N3
4-(3-bromophenyl)pyrimidine-2,5,6-d3 4-(3-bromophenyl)pyrimidine-2,5,6-d3 2256712-05-5 C10H7BrN2
4-(3-METHYL-1H-PYRAZOL-1-YL)PYRIDIN-2-AMINE 4-(3-METHYL-1H-PYRAZOL-1-YL)PYRIDIN-2-AMINE 1314354-36-3 C9H10N4
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazole 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazole 2256756-30-4 C15H17BF3N3O2
4-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDIN-2-AMINE 4-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDIN-2-AMINE 1314356-55-2 C9H10N4
4-(6-AMINOPYRIDIN-2-YL)BENZONITRILE 4-(6-AMINOPYRIDIN-2-YL)BENZONITRILE 1255638-22-2 C12H9N3
4-(ethoxy-d5)pyridin-3,5,6-d3-2-amine 4-(ethoxy-d5)pyridin-3,5,6-d3-2-amine 2259316-26-0 C7H10N2O
4-(methyl-d3)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl-2,5-d2)pyridine-3,5,6-d3 4-(methyl-d3)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl-2,5-d2)pyridine-3,5,6-d3 2256705-36-7 C15H20BN3O2
4-(methyl-d3)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl-2,5-d2)pyridine-2,5,6-d3 4-(methyl-d3)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-1-yl-2,5-d2)pyridine-2,5,6-d3 2256706-40-6 C15H20BN3O2
4-(tetrahydro-2H-pyran-2-yl)pyrimidin-2-ol 4-(tetrahydro-2H-pyran-2-yl)pyrimidin-2-ol 2222934-32-7 C9H12N2O2
4,5-Dibromo-2-(2-fluorophenyl)thiazole 4,5-Dibromo-2-(2-fluorophenyl)thiazole 1314355-07-1 C9H4Br2FNS
4,5-Dibromo-2-(2-pyridyl)thiazole 4,5-Dibromo-2-(2-pyridyl)thiazole 1314355-96-8 C8H4Br2N2S
4,5-Dibromo-2-(4-chlorophenyl)thiazole 4,5-Dibromo-2-(4-chlorophenyl)thiazole 1314355-91-3 C9H4Br2ClNS
4,5-Dibromo-2-(cyclopropyl)pyrimidine 4,5-Dibromo-2-(cyclopropyl)pyrimidine 1563528-78-8 C7H6Br2N2
4,5-Dibromo-2-ethylpyrimidine 4,5-Dibromo-2-ethylpyrimidine 1563534-88-2 C6H6Br2N2
4,6-Dichloro-2-(piperidin-3-yl)pyrimidine 4,6-Dichloro-2-(piperidin-3-yl)pyrimidine 1622835-88-4 C9H11Cl2N3
4-Amino-1-(4-cyanophenyl)imidazole 4-Amino-1-(4-cyanophenyl)imidazole 1353853-75-4 C10H8N4
4-Amino-2-(2-pyridyl)thiazole 4-Amino-2-(2-pyridyl)thiazole 93209-74-6 C8H7N3S
4-Amino-2-(2-tolyl)thiazole 4-Amino-2-(2-tolyl)thiazole 123970-58-1 C10H10N2S
4-Amino-2-(3-fluorophenyl)thiazole 4-Amino-2-(3-fluorophenyl)thiazole 1159816-71-3 C9H7FN2S
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