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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
4-Bromo-2-(4-methoxyphenyl)pyridine 4-Bromo-2-(4-methoxyphenyl)pyridine 916824-55-0 C12H10BrNO
4-Bromo-2-(4-trifluoromethylphenyl)thiazole 4-Bromo-2-(4-trifluoromethylphenyl)thiazole 1142196-44-8 C10H5BrF3NS
4-bromo-2-(methoxy-d3)pyrimidine-5,6-d2 4-bromo-2-(methoxy-d3)pyrimidine-5,6-d2 2256707-55-6 C5H5BrN2O
4-bromo-2-(oxetan-3-yl)pyridine 4-bromo-2-(oxetan-3-yl)pyridine 1823367-12-9 C8H8BrNO
4-Bromo-2-(thiazol-4-yl)pyridine 4-Bromo-2-(thiazol-4-yl)pyridine 1563530-81-3 C8H5BrN2S
4-Bromo-2-amino-5-(iso-propyl)pyrimidine 4-Bromo-2-amino-5-(iso-propyl)pyrimidine 1381936-60-2 C7H10BrN3
4-bromo-3-(1H-imidazol-1-yl-d3)pyridine 4-bromo-3-(1H-imidazol-1-yl-d3)pyridine 2256707-25-0 C8H6BrN3
4-Bromo-3-(2-pyridyl)pyridine 4-Bromo-3-(2-pyridyl)pyridine 1356406-44-4 C10H7BrN2
4-Bromo-3-(3,5-difluorophenyl)pyridine 4-Bromo-3-(3,5-difluorophenyl)pyridine 1374665-60-7 C11H6BrF2N
4-Bromo-3-(4-methoxyphenyl)pyridine 4-Bromo-3-(4-methoxyphenyl)pyridine 440112-18-5 C12H10BrNO
4-Bromo-3-(4-tert-butylphenyl)pyridine 4-Bromo-3-(4-tert-butylphenyl)pyridine 1563533-42-5 C15H16BrN
4-Bromo-3-(piperazin-1-yl)pyridine 4-Bromo-3-(piperazin-1-yl)pyridine 1563531-85-0 C9H12BrN3
4-Bromo-3-(tert-butyl)pyridine 4-Bromo-3-(tert-butyl)pyridine 1374664-82-0 C9H12BrN
4-Bromo-3-amino-6-(3-fluorophenyl)pyridine 4-Bromo-3-amino-6-(3-fluorophenyl)pyridine 1381934-09-3 C11H8BrFN2
4-Bromo-3-amino-6-(3-methylpiperidin-1-yl)pyridine 4-Bromo-3-amino-6-(3-methylpiperidin-1-yl)pyridine 1381934-74-2 C11H16BrN3
4-Bromo-3-amino-6-(4-trifluoromethylphenyl)pyridine 4-Bromo-3-amino-6-(4-trifluoromethylphenyl)pyridine 1381944-01-9 C12H8BrF3N2
4-Bromo-3-amino-6-(cyclopropyl)pyridine 4-Bromo-3-amino-6-(cyclopropyl)pyridine 1381933-95-4 C8H9BrN2
4-Bromo-5-(cyclohexyl)pyrimidine 4-Bromo-5-(cyclohexyl)pyrimidine 1563534-82-6 C10H13BrN2
4-Bromo-5-(n-propyl)-2-(diethylamino)thiazole 4-Bromo-5-(n-propyl)-2-(diethylamino)thiazole 1643562-89-3 C10H17BrN2S
4-Bromo-5-methyl-2-(cyclohexyl)pyridine 4-Bromo-5-methyl-2-(cyclohexyl)pyridine 1374665-35-6 C12H16BrN
4-Bromo-5-methyl-2-(iso-propyl)pyridine 4-Bromo-5-methyl-2-(iso-propyl)pyridine 1374664-85-3 C9H12BrN
4-Bromo-6-(3-tetrahydropyranyl)pyrimidine 4-Bromo-6-(3-tetrahydropyranyl)pyrimidine 1353855-51-2 C9H11BrN2O
4-Bromo-6-(4-methoxyphenyl)pyrimidine 4-Bromo-6-(4-methoxyphenyl)pyrimidine 1260842-76-9 C11H9BrN2O
4-Bromo-6-cyclohexylpyrimidine 4-Bromo-6-cyclohexylpyrimidine 1086382-19-5 C10H13BrN2
4-chloro-2-(methoxy-d3)pyrimidine-5,6-d2 4-chloro-2-(methoxy-d3)pyrimidine-5,6-d2 2259315-69-8 C5H5ClN2O
4-Chloro-2-hydroxy-5-ethylpyrimidine 4-Chloro-2-hydroxy-5-ethylpyrimidine 1563533-91-4 C6H7ClN2O
4-CHLORO-3-(1-BOC-PIPERIDIN-4-YL)PYRIDINE 4-CHLORO-3-(1-BOC-PIPERIDIN-4-YL)PYRIDINE 1563534-85-9 C15H21ClN2O2
4-CHLORO-3-(4-THIAZOLYL)PYRIDINE 4-CHLORO-3-(4-THIAZOLYL)PYRIDINE 1563533-54-9 C8H5ClN2S
4-Chloro-5-bromo-2-(2-furyl)pyrimidine 4-Chloro-5-bromo-2-(2-furyl)pyrimidine 1399479-66-3 C8H4BrClN2O
4-Chloro-5-bromo-2-(2-tolyl)pyrimidine 4-Chloro-5-bromo-2-(2-tolyl)pyrimidine 1399479-72-1 C11H8BrClN2
4-Chloro-5-bromo-2-(cyclobutoxy)pyrimidine 4-Chloro-5-bromo-2-(cyclobutoxy)pyrimidine 1399479-85-6 C8H8BrClN2O
4-Chloro-5-bromo-2-(tert-butyl)pyrimidine 4-Chloro-5-bromo-2-(tert-butyl)pyrimidine 1369942-72-2 C8H10BrClN2
4-CHLORO-5-CYCLOPROPYL-3-METHYLPYRIDIN-2-AMINE 4-CHLORO-5-CYCLOPROPYL-3-METHYLPYRIDIN-2-AMINE 1417518-36-5 C9H11ClN2
4-chloro-6-(methoxy-d3)pyrimidine-2,5-d2 4-chloro-6-(methoxy-d3)pyrimidine-2,5-d2 2259315-74-5 C5H5ClN2O
4-chloro-6-(tetrahydro-2H-pyran-2-yl)pyrimidine 4-chloro-6-(tetrahydro-2H-pyran-2-yl)pyrimidine 2222934-97-4 C9H11ClN2O
4-Hydroxy-2-(3-furyl)pyridine 4-Hydroxy-2-(3-furyl)pyridine 1159814-57-9 C9H7NO2
4-Hydroxy-2-methyl-6-(2-methyl-5-thiazolyl)pyrimidine 4-Hydroxy-2-methyl-6-(2-methyl-5-thiazolyl)pyrimidine 1159819-25-6 C9H9N3OS
4-Hydroxy-2-methyl-6-(5-pyrimidyl)pyrimidine 4-Hydroxy-2-methyl-6-(5-pyrimidyl)pyrimidine 1159818-54-8 C9H8N4O
4-Hydroxy-6-(2-methoxyphenyl)-2-cyclopropylpyrimidine 4-Hydroxy-6-(2-methoxyphenyl)-2-cyclopropylpyrimidine 1159819-73-4 C14H14N2O2
4-Hydroxy-6-(3-furyl)pyrimidine 4-Hydroxy-6-(3-furyl)pyrimidine 1159817-89-6 C8H6N2O2
4-PROPOXYPYRIDIN-3-YLAMINE 4-PROPOXYPYRIDIN-3-YLAMINE 173435-36-4 C8H12N2O
5-(3-bromophenyl)pyrimidine-2,4,6-d3 5-(3-bromophenyl)pyrimidine-2,4,6-d3 2256712-02-2 C10H7BrN2
5-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(4-(methyl-d3)-1H-imidazol-1-yl-2,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256706-81-5 C15H20BN3O2
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2,4,6-d3-3-amine 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2,4,6-d3-3-amine 2241874-97-3 C11H17BN2O2
5-(methoxy-d3)pyridin-3-amine 5-(methoxy-d3)pyridin-3-amine 1394130-05-2 C6H8N2O
5-(methyl-d3)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-3,5-d2)pyridine-3,4,6-d3 5-(methyl-d3)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl-3,5-d2)pyridine-3,4,6-d3 2256706-32-6 C15H20BN3O2
5-(tetrahydrofuran-3-yl)pyridin-2-ol 5-(tetrahydrofuran-3-yl)pyridin-2-ol 2222934-47-4 C9H11NO2
5-(Thiazol-5-yl)-1,3-dibromobenzene 5-(Thiazol-5-yl)-1,3-dibromobenzene 1563529-38-3 C9H5Br2NS
5-Amino-2-(2-trifluoromethylphenyl)thiazole 5-Amino-2-(2-trifluoromethylphenyl)thiazole 1159821-86-9 C10H7F3N2S
5-Amino-2-(4-tolyl)thiazole 5-Amino-2-(4-tolyl)thiazole 1159814-87-5 C10H10N2S
5-bromo-2-(1H-imidazol-1-yl-d3)pyridine-3,4,6-d3 5-bromo-2-(1H-imidazol-1-yl-d3)pyridine-3,4,6-d3 2256707-32-9 C8H6BrN3
5-BROMO-2-(2-METHYLPHENYL)PYRIDIN-4-AMINE 5-BROMO-2-(2-METHYLPHENYL)PYRIDIN-4-AMINE 1381942-58-0 C12H11BrN2
5-Bromo-2-(2-trifluoromethylphenyl)thiazole 5-Bromo-2-(2-trifluoromethylphenyl)thiazole 1159821-84-7 C10H5BrF3NS
5-Bromo-2-(3-tolyl)thiazole 5-Bromo-2-(3-tolyl)thiazole 1086382-56-0 C10H8BrNS
5-Bromo-2-(4-fluoro-2-methylphenyl)thiazole 5-Bromo-2-(4-fluoro-2-methylphenyl)thiazole 1159814-74-0 C10H7BrFNS
5-BROMO-2-(PYRIMIDIN-5-YL)PYRIDIN-4-AMINE 5-BROMO-2-(PYRIMIDIN-5-YL)PYRIDIN-4-AMINE 1381942-36-4 C9H7BrN4
5-Bromo-2,4-[di(n-propyl)]thiazole 5-Bromo-2,4-[di(n-propyl)]thiazole 1643577-09-6 C9H14BrNS
5-bromo-2-ethyl-3-(trifluoromethyl)pyridine 5-bromo-2-ethyl-3-(trifluoromethyl)pyridine 1346532-51-1 C8H7BrF3N
5-Bromo-4-(iso-propyl)-2-ethylthiazole 5-Bromo-4-(iso-propyl)-2-ethylthiazole 1643577-12-1 C8H12BrNS
5-Bromo-4-(n-propyl)-2-(morpholino)thiazole 5-Bromo-4-(n-propyl)-2-(morpholino)thiazole 1643562-97-3 C10H15BrN2OS
5-bromo-4-fluoro-2-(methoxy-d3)pyridine-3,6-d2 5-bromo-4-fluoro-2-(methoxy-d3)pyridine-3,6-d2 2294945-51-8 C6H5BrFNO
5-Bromo-4-methyl-2-(pyrrolidino)thiazole 5-Bromo-4-methyl-2-(pyrrolidino)thiazole 1518423-82-9 C8H11BrN2S
5-fluoro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-2-yl)pyridine 5-fluoro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazol-2-yl)pyridine 2256755-52-7 C14H17BFN3O2
5-HYDROXY-2,4'-BIPYRIDINE 5-HYDROXY-2,4'-BIPYRIDINE 1159816-97-3 C10H8N2O
6-(2-AMINOPHENYL)PYRIDIN-2-AMINE 6-(2-AMINOPHENYL)PYRIDIN-2-AMINE 902745-37-3 C11H11N3
6-(3-AMINOPHENYL)PYRIDIN-3-AMINE 6-(3-AMINOPHENYL)PYRIDIN-3-AMINE 1233714-46-9 C11H11N3
6-(methoxy-d3)pyridin-3-amine 6-(methoxy-d3)pyridin-3-amine 1202760-61-9 C6H8N2O
6-(tert-butoxy)-N-ethyl-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 6-(tert-butoxy)-N-ethyl-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 2256755-22-1 C18H31BN2O3
6-(tetrahydro-2H-pyran-2-yl)pyrimidin-4-amine 6-(tetrahydro-2H-pyran-2-yl)pyrimidin-4-amine 2222935-00-2 C9H13N3O
6-(tetrahydrofuran-3-yl)pyridin-3-ol 6-(tetrahydrofuran-3-yl)pyridin-3-ol 2222935-49-9 C9H11NO2
6-bromopyridin-2,4,5-d3-3-ol 6-bromopyridin-2,4,5-d3-3-ol 2241864-94-6 C5H4BrNO
Methyl 4,5-dibromothiazole-2-carboxylate Methyl 4,5-dibromothiazole-2-carboxylate 1314355-85-5 C5H3Br2NO2S
N-Boc-2,3-Dihydro-6-bromo-[1,4]oxazine N-Boc-2,3-Dihydro-6-bromo-[1,4]oxazine 1622843-89-3 C9H14BrNO3
tert-butyl 3-(4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazol-2-yl)pyrrolidine-1-carboxylate tert-butyl 3-(4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazol-2-yl)pyrrolidine-1-carboxylate 2256758-24-2 C19H31BN2O4S
TERT-BUTYL 4-(2-AMINOPYRIDIN-4-YL)-1,2,3,6-TETRAHYDROPYRIDINE-1-CARBOXYLATE TERT-BUTYL 4-(2-AMINOPYRIDIN-4-YL)-1,2,3,6-TETRAHYDROPYRIDINE-1-CARBOXYLATE 1563532-60-4 C15H21N3O2
tert-butyl 4-(4-aminopyridin-2-yl)piperidine-1-carboxylate tert-butyl 4-(4-aminopyridin-2-yl)piperidine-1-carboxylate 1206249-06-0 C15H23N3O2
tert-butyl 4-(5-bromopyrimidin-2-yl)piperidine-1-carboxylate tert-butyl 4-(5-bromopyrimidin-2-yl)piperidine-1-carboxylate 1211538-92-9 C14H20BrN3O2
tert-butyl 4-(6-aminopyrimidin-4-yl)piperidine-1-carboxylate tert-butyl 4-(6-aminopyrimidin-4-yl)piperidine-1-carboxylate 1440427-67-7 C14H22N4O2
2'-(Methylthio)-7',8'-dihydro-6'H-spiro[cyclohexane-1,9'-pyrazino[1',2':1,5]pyrrolo[2,3-d]pyrimidin]-6'-one 2'-(Methylthio)-7',8'-dihydro-6'H-spiro[cyclohexane-1,9'-pyrazino[1',2':1,5]pyrrolo[2,3-d]pyrimidin]-6'-one 2170747-00-7 C15H18N4OS
6,7-Dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol 6,7-Dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol 1557178-09-2 C6H8N2O2
5-Bromo-2-pyrazol-1-yl-benzonitrile 5-Bromo-2-pyrazol-1-yl-benzonitrile 742100-11-4 C10H6BrN3
1-(PHENYLSULFINYL)PIPERIDINE  97 1-(PHENYLSULFINYL)PIPERIDINE 97 4972-31-0 C11H15NOS
2-(3-Tetrahydrofuranyl)bromobenzene 2-(3-Tetrahydrofuranyl)bromobenzene 1353856-24-2 C10H11BrO
1H-Imidazole, 1,1'-(oxydi-4,1-phenylene)bis- 1H-Imidazole, 1,1'-(oxydi-4,1-phenylene)bis- 13120-43-9 C18H14N4O
[[(1,3,5-Triazine-2,4,6-triyl)tris(benzene-4,1-diyl)]triboronic acid] [[(1,3,5-Triazine-2,4,6-triyl)tris(benzene-4,1-diyl)]triboronic acid] 910231-21-9 C21H18B3N3O6
1H-1,2,4-Triazole, 5-(2-fluorophenyl)- 1H-1,2,4-Triazole, 5-(2-fluorophenyl)- 1505273-47-1 C8H6FN3
1H-Imidazole, 1,1'-(2,5-dimethyl-1,4-phenylene)bis- 1H-Imidazole, 1,1'-(2,5-dimethyl-1,4-phenylene)bis- 1347702-73-1 C14H14N4
4,6- diisopropylpyrimidin-5-amine 4,6- diisopropylpyrimidin-5-amine 2168417-89-6 C10H17N3
4,4'-Bi-1H-pyrazole 4,4'-Bi-1H-pyrazole 25240-33-9 C6H6N4
2,4,6-trichlorobenzimidazole 2,4,6-trichlorobenzimidazole 142356-47-6 C7H3Cl3N2
AOI-BP AOI-BP 885331-05-5 C11H15N3O3
4-[(S)-4-Boc-2-methyl-1-piperazinyl]-6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(2-isopropyl-4-methyl-3-pyridyl)pyrido[2,3-d]pyrimidin-2(1H)-one 4-[(S)-4-Boc-2-methyl-1-piperazinyl]-6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(2-isopropyl-4-methyl-3-pyridyl)pyrido[2,3-d]pyrimidin-2(1H)-one 2252403-85-1 C32H36F2N6O4
2,7-dichloro-1,6-naphthyridine 2,7-dichloro-1,6-naphthyridine 1393583-67-9 C8H4Cl2N2
1-Piperidinecarboxylic acid, 3-methyl-4-oxo-, 1,1-dimethylethyl ester, (3R)- 1-Piperidinecarboxylic acid, 3-methyl-4-oxo-, 1,1-dimethylethyl ester, (3R)- 2091951-57-2 C11H19NO3
2,2'-Bioxazole, 4,4'-bis(1,1-dimethylethyl)-4,4',5,5'-tetrahydro-, (4S,4'S)- 2,2'-Bioxazole, 4,4'-bis(1,1-dimethylethyl)-4,4',5,5'-tetrahydro-, (4S,4'S)- 135565-31-0 C14H24N2O2
7-methyl-2H,3H,4H-pyrido[1,2-a]pyrimidin-3-ol hydrochloride 7-methyl-2H,3H,4H-pyrido[1,2-a]pyrimidin-3-ol hydrochloride 6056-42-4 C9H12N2O.HCl
Piperazine, 1-(3-bromo-4-pyridinyl)- Piperazine, 1-(3-bromo-4-pyridinyl)- 1288988-08-8 C9H12BrN3
(2S,3S)-3-Hydroxypyrrolidine-2-carboxamide hydrochloride (2S,3S)-3-Hydroxypyrrolidine-2-carboxamide hydrochloride 426844-45-3 C5H11ClN2O2
(5,6,7,8-Tetrahydroimidazo[1,2-a]pyridin-7-yl)methanamine dihydrochloride (5,6,7,8-Tetrahydroimidazo[1,2-a]pyridin-7-yl)methanamine dihydrochloride 1803583-23-4 C8H14ClN3
7-Methoxy-5-(methylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine 7-Methoxy-5-(methylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine 1350563-51-7 C6H7N5OS
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