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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-Amino-5-bromo-6-(3-furyl)pyridine 3-Amino-5-bromo-6-(3-furyl)pyridine 1399480-18-2 C9H7BrN2O
3-Amino-5-bromo-6-(3-trifluoromethylphenyl)pyridine 3-Amino-5-bromo-6-(3-trifluoromethylphenyl)pyridine 1399480-83-1 C12H8BrF3N2
3-Amino-6-(2-methylthiazol-4-yl)pyridine 3-Amino-6-(2-methylthiazol-4-yl)pyridine 1159821-77-8 C9H9N3S
3-BROMO-1-(OXAN-4-YL)-1H-PYRAZOLE 3-BROMO-1-(OXAN-4-YL)-1H-PYRAZOLE 1227954-60-0 C8H11BrN2O
3-Bromo-2-(2-cyanophenyl)pyridine 3-Bromo-2-(2-cyanophenyl)pyridine 1563533-28-7 C12H7BrN2
3-Bromo-2-(3,4-difluorophenyl)pyridine 3-Bromo-2-(3,4-difluorophenyl)pyridine 1417517-95-3 C11H6BrF2N
3-Bromo-2-(4-aminophenyl)pyridine 3-Bromo-2-(4-aminophenyl)pyridine 1417518-76-3 C11H9BrN2
3-Bromo-2-(4-ethylphenyl)pyridine 3-Bromo-2-(4-ethylphenyl)pyridine 1563531-74-7 C13H12BrN
3-Bromo-2-(cyclopentyl)pyridine 3-Bromo-2-(cyclopentyl)pyridine 1417517-92-0 C10H12BrN
3-bromo-2-(methoxy-d3)pyridine-4,5,6-d3 3-bromo-2-(methoxy-d3)pyridine-4,5,6-d3 2256707-69-2 C6BrD6NO
3-BROMO-2-(THIOPHEN-2-YL)PYRIDIN-4-AMINE 3-BROMO-2-(THIOPHEN-2-YL)PYRIDIN-4-AMINE 1381941-93-0 C9H7BrN2S
3-BROMO-2-[3-(TRIFLUOROMETHYL)PHENYL]PYRIDIN-4-AMINE 3-BROMO-2-[3-(TRIFLUOROMETHYL)PHENYL]PYRIDIN-4-AMINE 1381934-16-2 C12H8BrF3N2
3-Bromo-4-(2-cyanophenyl)pyridine 3-Bromo-4-(2-cyanophenyl)pyridine 335642-96-1 C12H7BrN2
3-Bromo-4-(3-bromophenyl)pyridine 3-Bromo-4-(3-bromophenyl)pyridine 1563531-29-2 C11H7Br2N
3-BROMO-4-(3-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 3-BROMO-4-(3-METHYL-1H-PYRAZOL-1-YL)PYRIDINE 1289021-10-8 C9H8BrN3
3-BROMO-4-(4-THIAZOLYL)PYRIDINE 3-BROMO-4-(4-THIAZOLYL)PYRIDINE 1563533-07-2 C8H5BrN2S
3-Bromo-4-(cyclohexyl)pyridine 3-Bromo-4-(cyclohexyl)pyridine 90731-97-8 C11H14BrN
3-Bromo-4-amino-6-(N-methylpiperazin-1-yl)pyridine 3-Bromo-4-amino-6-(N-methylpiperazin-1-yl)pyridine 1381934-11-7 C10H15BrN4
3-bromo-5-(1H-imidazol-1-yl-d3)pyridine 3-bromo-5-(1H-imidazol-1-yl-d3)pyridine 2256707-27-2 C8H6BrN3
3-Bromo-5-(2-aminophenyl)pyridine 3-Bromo-5-(2-aminophenyl)pyridine 1314353-91-7 C11H9BrN2
3-Bromo-5-(4-methyl-1H-pyrazol-1-yl)pyridine 3-Bromo-5-(4-methyl-1H-pyrazol-1-yl)pyridine 1289270-48-9 C9H8BrN3
3-Bromo-5-(morpholin-2-yl)pyridine 3-Bromo-5-(morpholin-2-yl)pyridine 1211523-96-4 C9H11BrN2O
3-Bromo-5-(n-propyl)pyridine 3-Bromo-5-(n-propyl)pyridine 1314356-70-1 C8H10BrN
3-Bromo-6-(2-trifluoromethylphenyl)pyridine 3-Bromo-6-(2-trifluoromethylphenyl)pyridine 1215071-94-5 C12H7BrF3N
3-Bromo-6-(4-methylimidazol-1-yl)pyridazine 3-Bromo-6-(4-methylimidazol-1-yl)pyridazine 1027513-47-8 C8H7BrN4
3-BROMO-6-(OXOLAN-3-YLOXY)PYRIDAZINE 3-BROMO-6-(OXOLAN-3-YLOXY)PYRIDAZINE 1622834-58-5 C8H9BrN2O2
3-Cyclopropyl-5-(thiazol-4-yl)bromobenzene 3-Cyclopropyl-5-(thiazol-4-yl)bromobenzene 1563533-25-4 C12H10BrNS
3-Hydroxy-2-(3-fluorophenyl)pyridine 3-Hydroxy-2-(3-fluorophenyl)pyridine 1214377-76-0 C11H8FNO
3-Hydroxy-2,2'-bipyridine 3-Hydroxy-2,2'-bipyridine 87385-12-4 C10H8N2O
3-Hydroxy-5-(1H-pyrrol-1-yl)pyridine 3-Hydroxy-5-(1H-pyrrol-1-yl)pyridine 1314355-74-2 C9H8N2O
3-Hydroxy-5-(3-chlorophenyl)pyridine 3-Hydroxy-5-(3-chlorophenyl)pyridine 1258616-41-9 C11H8ClNO
3-Hydroxy-5-(3-methylpiperidin-1-yl)pyridine 3-Hydroxy-5-(3-methylpiperidin-1-yl)pyridine 1314355-80-0 C11H16N2O
3-Hydroxy-5-(4-trifluoromethylphenyl)pyridine 3-Hydroxy-5-(4-trifluoromethylphenyl)pyridine 1261497-16-8 C12H8F3NO
3-Hydroxy-6-(3-tolyl)pyridine 3-Hydroxy-6-(3-tolyl)pyridine 1255638-58-4 C12H11NO
3-Methoxy-5-(thiazol-5-yl)bromobenzene 3-Methoxy-5-(thiazol-5-yl)bromobenzene 1563532-80-8 C10H8BrNOS
4-(1H-imidazol-1-yl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 4-(1H-imidazol-1-yl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 2256709-65-4 C14H12BD6N3O2
4-(2-Amino-5-pyrimidyl)thiazole 4-(2-Amino-5-pyrimidyl)thiazole 1215074-26-2 C7H6N4S
4-(2-bromophenyl)-2-chloropyrimidine-5,6-d2 4-(2-bromophenyl)-2-chloropyrimidine-5,6-d2 2256711-32-5 C10H6BrClN2
4-(2-bromophenyl)pyrimidine-2,5,6-d3 4-(2-bromophenyl)pyrimidine-2,5,6-d3 2256711-26-7 C10H7BrN2
4-(2-Tollyl)thiazole 4-(2-Tollyl)thiazole 383145-34-4 C10H9NS
4-(3-AMINOPYRIDIN-2-YL)BENZONITRILE 4-(3-AMINOPYRIDIN-2-YL)BENZONITRILE 1563530-07-3 C12H9N3
4-(3-BROMOPHENYL)PYRIDIN-3-AMINE 4-(3-BROMOPHENYL)PYRIDIN-3-AMINE 1368226-69-0 C11H9BrN2
4-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256706-48-4 C15H20BN3O2
4-(4-METHYL-1H-IMIDAZOL-1-YL)PYRIDIN-2-AMINE 4-(4-METHYL-1H-IMIDAZOL-1-YL)PYRIDIN-2-AMINE 1251863-90-7 C9H10N4
4-(4-TERT-BUTYLPHENYL)PYRIDIN-3-AMINE 4-(4-TERT-BUTYLPHENYL)PYRIDIN-3-AMINE 1228179-80-3 C15H18N2
4-(6-(tert-butoxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine 4-(6-(tert-butoxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine 2256755-13-0 C19H31BN2O4
4-(methoxy-d3)pyridin-3-amine 4-(methoxy-d3)pyridin-3-amine 2259316-31-7 C6H5D3N2O
4-(methyl-d3)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-4,5-d2)pyrimidine-5,6-d2 4-(methyl-d3)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-4,5-d2)pyrimidine-5,6-d2 2256705-99-2 C14H19BN4O2
4-(THIOPHEN-3-YL)PYRIDIN-2-AMINE 4-(THIOPHEN-3-YL)PYRIDIN-2-AMINE 1159820-91-3 C9H8N2S
4,5-Dibromo-1-(iso-butyl)-2-ethyl-1H-imidazole 4,5-Dibromo-1-(iso-butyl)-2-ethyl-1H-imidazole 1622839-73-9 C9H14Br2N2
4,5-Dibromo-2-(2-chlorophenyl)thiazole 4,5-Dibromo-2-(2-chlorophenyl)thiazole 1314356-27-8 C9H4Br2ClNS
4,5-Dibromo-2-(3-trifluoromethylphenyl)thiazole 4,5-Dibromo-2-(3-trifluoromethylphenyl)thiazole 1314357-34-0 C10H4Br2F3NS
4,5-Dibromo-2-(cyclopentyl)thiazole 4,5-Dibromo-2-(cyclopentyl)thiazole 1314357-30-6 C8H9Br2NS
4,5-Dibromo-2-(ethoxy)thiazole 4,5-Dibromo-2-(ethoxy)thiazole 1314357-21-5 C5H5Br2NOS
4,5-Dibromo-2-cyanothiazole 4,5-Dibromo-2-cyanothiazole 1314354-41-0 C4Br2N2S
4,6-DICHLORO-2-(OXAN-4-YL)PYRIMIDINE 4,6-DICHLORO-2-(OXAN-4-YL)PYRIMIDINE 1045861-18-4 C9H10Cl2N2O
4-Amino-2-(4-chlorophenyl)thiazole 4-Amino-2-(4-chlorophenyl)thiazole 123970-68-3 C9H7ClN2S
4-Amino-2-(4-fluorophenyl)thiazole 4-Amino-2-(4-fluorophenyl)thiazole 1159816-99-5 C9H7FN2S
4-Amino-2-(ethylmethylamino)pyridine 4-Amino-2-(ethylmethylamino)pyridine 1248692-37-6 C8H13N3
4-Amino-2-(pyrrolidin-3-yl)thiazole 4-Amino-2-(pyrrolidin-3-yl)thiazole 1159821-10-9 C7H11N3S
4-Amino-2-(thiazol-5-yl)pyridine 4-Amino-2-(thiazol-5-yl)pyridine 1563532-67-1 C8H7N3S
4-Amino-2-chloro-3-bromo-5-(3-fluorophenyl)pyridine 4-Amino-2-chloro-3-bromo-5-(3-fluorophenyl)pyridine 1563534-55-3 C11H7BrClFN2
4-Amino-2-chloro-3-bromo-5-(3-trifluoromethylphenyl)pyridine 4-Amino-2-chloro-3-bromo-5-(3-trifluoromethylphenyl)pyridine 1563531-50-9 C12H7BrClF3N2
4-Amino-2-chloro-3-bromo-5-(thiazol-4-yl)pyridine 4-Amino-2-chloro-3-bromo-5-(thiazol-4-yl)pyridine 1563532-05-7 C8H5BrClN3S
4-Amino-2-chloro-3-bromo-5-phenylpyridine 4-Amino-2-chloro-3-bromo-5-phenylpyridine 1563533-75-4 C11H8BrClN2
4-Amino-2-phenyl-6-(2-methyl-5-thiazolyl)pyrimidine 4-Amino-2-phenyl-6-(2-methyl-5-thiazolyl)pyrimidine 1159818-68-4 C14H12N4S
4-Amino-2-phenyl-6-(5-pyrimidyl)pyrimidine 4-Amino-2-phenyl-6-(5-pyrimidyl)pyrimidine 1159821-75-6 C14H11N5
4-AMINO-3-(4-FLUORO-2-METHYLPHENYL)PYRIDINE 4-AMINO-3-(4-FLUORO-2-METHYLPHENYL)PYRIDINE 1258632-24-4 C12H11FN2
4-AMINO-3-(5-THIAZOLYL)PYRIDINE 4-AMINO-3-(5-THIAZOLYL)PYRIDINE 1563530-68-6 C8H7N3S
4-Amino-3,5-dibromo-2-(2-methylimidazol-1-yl)pyridine 4-Amino-3,5-dibromo-2-(2-methylimidazol-1-yl)pyridine 1563533-76-5 C9H8Br2N4
4-Amino-3,5-dibromo-2-(3-tolyl)pyridine 4-Amino-3,5-dibromo-2-(3-tolyl)pyridine 1563533-63-0 C12H10Br2N2
4-Amino-3,5-dibromo-2-(4-methoxyphenyl)pyridine 4-Amino-3,5-dibromo-2-(4-methoxyphenyl)pyridine 1563531-75-8 C12H10Br2N2O
4-Amino-3,5-dibromo-2-(iso-butyl)pyridine 4-Amino-3,5-dibromo-2-(iso-butyl)pyridine 1563535-16-9 C9H12Br2N2
4-Amino-3,5-dibromo-2-(piperidin-4-yl)pyridine 4-Amino-3,5-dibromo-2-(piperidin-4-yl)pyridine 1563529-90-7 C10H13Br2N3
4-Amino-3,5-dibromo-2-methylethylaminopyridine 4-Amino-3,5-dibromo-2-methylethylaminopyridine 1563534-35-9 C8H11Br2N3
4-Amino-3-bromo-2-(tert-butyl)pyridine 4-Amino-3-bromo-2-(tert-butyl)pyridine 1563534-44-0 C9H13BrN2
4-Amino-3-bromo-6-(2-methyl-4-fluorophenyl)pyridine 4-Amino-3-bromo-6-(2-methyl-4-fluorophenyl)pyridine 1563532-09-1 C12H10BrFN2
4-Amino-3-bromo-6-(sec-butyl)pyridine 4-Amino-3-bromo-6-(sec-butyl)pyridine 1563529-18-9 C9H13BrN2
4-Amino-3-bromo-6-methylethylaminopyridine 4-Amino-3-bromo-6-methylethylaminopyridine 1446413-22-4 C8H12BrN3
4-Amino-6-(2-fluorophenyl)pyrimidine 4-Amino-6-(2-fluorophenyl)pyrimidine 1159820-15-1 C10H8FN3
4-Amino-6-(2-methyl-4-thiazolyl)-2-cyclopropylpyrimidine 4-Amino-6-(2-methyl-4-thiazolyl)-2-cyclopropylpyrimidine 1159820-56-0 C11H12N4S
4-Amino-6-(4-methoxyphenyl)pyrimidine 4-Amino-6-(4-methoxyphenyl)pyrimidine 791524-73-7 C11H11N3O
4-Amino-6-(cyclohexyl)pyrimidine 4-Amino-6-(cyclohexyl)pyrimidine 1159819-98-3 C10H15N3
4-Bromo-1-(3-methoxyphenyl)pyrazole 4-Bromo-1-(3-methoxyphenyl)pyrazole 1353856-04-8 C10H9BrN2O
4-Bromo-1-(oxolan-3-yl)-1H-1,2,3-triazole 4-Bromo-1-(oxolan-3-yl)-1H-1,2,3-triazole 1622834-25-6 C6H8BrN3O
4-bromo-1-(tetrahydrofuran-2-yl)-1H-pyrazole 4-bromo-1-(tetrahydrofuran-2-yl)-1H-pyrazole 1851602-84-0 C7H9BrN2O
4-bromo-2-(1H-imidazol-1-yl-d3)pyridine-3,5,6-d3 4-bromo-2-(1H-imidazol-1-yl-d3)pyridine-3,5,6-d3 2256707-33-0 C8BrD6N3
4-bromo-2-(1H-pyrazol-1-yl-d3)pyrimidine-5,6-d2 4-bromo-2-(1H-pyrazol-1-yl-d3)pyrimidine-5,6-d2 2256707-10-3 C7H5BrN4
4-Bromo-2-(2-trifluoromethylphenyl)thiazole 4-Bromo-2-(2-trifluoromethylphenyl)thiazole 1159817-97-6 C10H5BrF3NS
4-Bromo-2-(3-hydroxypyrrolidin-1-yl)pyridine 4-Bromo-2-(3-hydroxypyrrolidin-1-yl)pyridine 1159819-21-2 C9H11BrN2O
4-Bromo-2-(3-pyridyl)pyridine 4-Bromo-2-(3-pyridyl)pyridine 62913-27-3 C10H7BrN2
4-Bromo-2-(3-thienyl)pyridine 4-Bromo-2-(3-thienyl)pyridine 1142194-19-1 C9H6BrNS
4-Bromo-2-(5-pyrimidyl)thiazole 4-Bromo-2-(5-pyrimidyl)thiazole 1159815-56-1 C7H4BrN3S
4-Bromo-2,3-dihydrofuran 4-Bromo-2,3-dihydrofuran 1430811-55-4 C4H5BrO
4-Bromo-2-methyl-1-(cyclopropyl)-1H-imidazole 4-Bromo-2-methyl-1-(cyclopropyl)-1H-imidazole 1563531-30-5 C7H9BrN2
4-BROMO-3-(2-METHYLIMIDAZOL-1-YL)PYRIDINE 4-BROMO-3-(2-METHYLIMIDAZOL-1-YL)PYRIDINE 1563531-71-4 C9H8BrN3
4-Bromo-3-(2-trifluoromethylphenyl)pyridine 4-Bromo-3-(2-trifluoromethylphenyl)pyridine 1374664-84-2 C12H7BrF3N
4-Bromo-3-(4-ethylphenyl)pyridine 4-Bromo-3-(4-ethylphenyl)pyridine 1563535-00-1 C13H12BrN
4-BROMO-3-(4-METHYLPIPERIDIN-1-YL)PYRIDINE 4-BROMO-3-(4-METHYLPIPERIDIN-1-YL)PYRIDINE 1563534-02-0 C11H15BrN2
4-Bromo-3-(pyrazol-4-yl)pyridine 4-Bromo-3-(pyrazol-4-yl)pyridine 1563533-17-4 C8H6BrN3
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