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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
1-benzyltriazole 1-benzyltriazole 4368-68-7 C9H9N3
9-phenyl-1,7-diazabicyclo[4.3.0]nona-2,4,6,8-tetraene 9-phenyl-1,7-diazabicyclo[4.3.0]nona-2,4,6,8-tetraene 92961-15-4 C13H10N2
6-amino-1-((2S,4R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxypyrrolidin-1-yl)hexan-1-one 6-amino-1-((2S,4R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxypyrrolidin-1-yl)hexan-1-one
Pyridine, 2-(3-oxetanyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Pyridine, 2-(3-oxetanyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2223043-57-8 C14H20BNO3
furan-3,4-diyldimethanol furan-3,4-diyldimethanol 14496-24-3 C6H8O3
5H-indeno[1,2-b]pyridine 5H-indeno[1,2-b]pyridine 244-99-5 C12H9N
N,N-dimethylthio-2-thioxoimidazolidine-1-carboxamide N,N-dimethylthio-2-thioxoimidazolidine-1-carboxamide 935-75-1 C6H11N3OS3
1H-1,2,3-Triazole, 4,5-dimethyl- 1H-1,2,3-Triazole, 4,5-dimethyl- 42964-73-8 C4H7N3
Pyridine, 2-bromo-4-fluoro-3-iodo- Pyridine, 2-bromo-4-fluoro-3-iodo- 1805500-88-2 C5H2BrFIN
5-Hexynoic acid, 6-[2-(methylsulfonyl)-5-pyrimidinyl]- 5-Hexynoic acid, 6-[2-(methylsulfonyl)-5-pyrimidinyl]- 2356229-58-6 C11H12N2O4S
2-(pyrrolidinyl)pyrimidin-4-amine 2-(pyrrolidinyl)pyrimidin-4-amine 33851-99-9 C8H12N4
2,5-Bis(octyldithio)-1,3,4-thiadiazole 2,5-Bis(octyldithio)-1,3,4-thiadiazole 13539-13-4 C18H34N2S5
3-nitrocarbazole 3-nitrocarbazole 3077-85-8 C12H8N2O2
4,5-dihydro-2-vinyl-1H-imidazole 4,5-dihydro-2-vinyl-1H-imidazole 10577-96-5 C5H8N2
Pyridine, 4-bromo-2,6-diiodo- Pyridine, 4-bromo-2,6-diiodo- 1206249-77-5 C5H2BrI2N
Pyridine, 5-(1-azetidinyl)-2-bromo- Pyridine, 5-(1-azetidinyl)-2-bromo- 2363787-83-9 C8H9BrN2
4-(2,5-dibutoxy-4-nitrophenyl)morpholine 4-(2,5-dibutoxy-4-nitrophenyl)morpholine 86-15-7 C18H28N2O5
Pyrimidine, 2-(4-chloro-2-pyridinyl)- Pyrimidine, 2-(4-chloro-2-pyridinyl)- 2157370-48-2 C9H6ClN3
2-PYRIDIN-2-YL-PIPERAZINE 2-PYRIDIN-2-YL-PIPERAZINE 111759-97-8 C9H13N3
Tolytriazole sodium salt Tolytriazole sodium salt 64665-57-2 C7H6N3Na
1-(4-Nitrobenzyl)-1H-imidazole 1-(4-Nitrobenzyl)-1H-imidazole 18994-90-6 C10H9N3O2
2,6-Pyridinedicarboxamide, N2,N6-bis[(diethylamino)thioxomethyl]- 2,6-Pyridinedicarboxamide, N2,N6-bis[(diethylamino)thioxomethyl]- 320408-75-1 C17H25N5O2S2
Pyridine, 2-(4-piperidinyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Pyridine, 2-(4-piperidinyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1402166-08-8 C16H25BN2O2
2-(Methylcarboxy)pyridine-5-boronic Acid Pinacol Ester-D3 2-(Methylcarboxy)pyridine-5-boronic Acid Pinacol Ester-D3 2368223-39-4 C13H18BNO4
1-Azetidinecarboxylic acid, 3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]-, 1,1-dimethylethyl ester 1-Azetidinecarboxylic acid, 3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]-, 1,1-dimethylethyl ester 2223045-84-7 C19H29BN2O4
3-Pyridazinamine, 6-(3-methylphenyl)- 3-Pyridazinamine, 6-(3-methylphenyl)- 113121-50-9 C11H11N3
4-Morpholinecarboxylic acid, 3-(3-bromophenyl)-, 1,1-dimethylethyl ester 4-Morpholinecarboxylic acid, 3-(3-bromophenyl)-, 1,1-dimethylethyl ester 2322859-05-0 C15H20BrNO3
Oxazole, 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Oxazole, 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2710297-26-8 C10H16BNO3
4,4,4',4',5,5,5',5'-octaethyl-2,2'-bi(1,3,2-dioxaborolane) 4,4,4',4',5,5,5',5'-octaethyl-2,2'-bi(1,3,2-dioxaborolane) 2247367-07-1 C20H40B2O4
2-Thiophenamine, 5-(1,1-dimethylethyl)- 2-Thiophenamine, 5-(1,1-dimethylethyl)- 1260667-23-9 C8H13NS
L-Proline, 1-(2-naphthalenylacetyl)- (9CI) L-Proline, 1-(2-naphthalenylacetyl)- (9CI) 130654-11-4 C17H17NO3
Pyrimidine-2,4,5,6-d4 Pyrimidine-2,4,5,6-d4 2037-23-2 C4H4N2
3H-Imidazo[4,5-c]pyridine-3,5,6(4H)-tricarboxylic acid, 6,7-dihydro-, 3,5-bis(1,1-dimethylethyl) ester, (6S)- 3H-Imidazo[4,5-c]pyridine-3,5,6(4H)-tricarboxylic acid, 6,7-dihydro-, 3,5-bis(1,1-dimethylethyl) ester, (6S)- 1415602-89-9 C17H25N3O6
Pyrimidine, 5-bromo-4-(difluoromethyl)- Pyrimidine, 5-bromo-4-(difluoromethyl)- 1780524-96-0 C5H3BrF2N2
MEHYL-7-AZAINDOLE-4-CARBOXYLATE MEHYL-7-AZAINDOLE-4-CARBOXYLATE 351439-07-1 C9H8N2O2
4H-1,2,4-Triazol-3-amine,4-ethyl-5-methyl- 4H-1,2,4-Triazol-3-amine,4-ethyl-5-methyl- 254908-77-5 C5H10N4
5-isopropyluracil 5-isopropyluracil 17432-95-0 C7H10N2O2
L-Lysine, N2-[[[(1S)-4-(1,1-dimethylethoxy)-1-[(1,1-dimethylethoxy)carbonyl]-4-oxobutyl]amino]carbonyl]-N6-[3-(2-naphthalenyl)-L-alanyl]-, 1,1-dimethylethyl ester L-Lysine, N2-[[[(1S)-4-(1,1-dimethylethoxy)-1-[(1,1-dimethylethoxy)carbonyl]-4-oxobutyl]amino]carbonyl]-N6-[3-(2-naphthalenyl)-L-alanyl]-, 1,1-dimethylethyl ester 2367588-01-8 C37H56N4O8
Piperazine, 1-(bromoacetyl)-4-methyl- (9CI) Piperazine, 1-(bromoacetyl)-4-methyl- (9CI) 112257-15-5 C7H13BrN2O
Pyridine, 4-ethyl-3-fluoro- (9CI) Pyridine, 4-ethyl-3-fluoro- (9CI) 137234-73-2 C7H8FN
(2R,4R)-4-fluoro-2-methylpyrrolidine (2R,4R)-4-fluoro-2-methylpyrrolidine
1H-1,2,4-Triazole, 5-bromo-3-(2-fluorophenyl)- 1H-1,2,4-Triazole, 5-bromo-3-(2-fluorophenyl)- 1782574-00-8 C8H5BrFN3
1H-Pyrrole, 1-(tetrahydro-3-furanyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1H-Pyrrole, 1-(tetrahydro-3-furanyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2223006-69-5 C14H22BNO3
Formamide, N-1H-benzimidazol-4-yl- (9CI) Formamide, N-1H-benzimidazol-4-yl- (9CI) 137654-47-8 C8H7N3O
(2S,4S)-4-fluoro-2-methylpyrrolidine hydrochloride (2S,4S)-4-fluoro-2-methylpyrrolidine hydrochloride 2828444-34-2 C5H11ClFN
2-pyridin-2-ylpyrimidine-5-carboxylic acid 2-pyridin-2-ylpyrimidine-5-carboxylic acid 933988-22-8 C10H7N3O2
4-Pyrimidinamine, 2-(4-methylphenyl)- (9CI) 4-Pyrimidinamine, 2-(4-methylphenyl)- (9CI) 114523-62-5 C11H11N3
Pyrimidine, 5-(bromomethyl)-2-(trifluoromethyl)- (9CI) Pyrimidine, 5-(bromomethyl)-2-(trifluoromethyl)- (9CI) 198404-35-2 C6H4BrF3N2
2-Pyridinecarboxylic acid, 4-bromo-6-cyclopropyl-, methyl ester 2-Pyridinecarboxylic acid, 4-bromo-6-cyclopropyl-, methyl ester 2645419-13-0 C10H10BrNO2
2(1H)-Quinoxalinone, 7-(bromomethyl)-8-fluoro-3-methyl- 2(1H)-Quinoxalinone, 7-(bromomethyl)-8-fluoro-3-methyl- 2756333-93-2 C10H8BrFN2O
2,5-Dimethyl-1H-imidazole-4-carboxaldehyde 2,5-Dimethyl-1H-imidazole-4-carboxaldehyde 68282-52-0 C6H8N2O
2,1,3-Benzothiadiazole 2,1,3-Benzothiadiazole 273-13-2 C6H4N2S
2-triisopropylsilyl oxazole 2-triisopropylsilyl oxazole 433332-27-5 C12H23NOSi
Domazoline Domazoline 6043-01-2 C14H20N2O2
(2-METHYLIMIDAZO[1,2-A]PYRIDIN-3-YL)METHANOL (2-METHYLIMIDAZO[1,2-A]PYRIDIN-3-YL)METHANOL 30489-44-2 C9H10N2O
ETHYL IMIDAZO[2,1-B][1,3]BENZOTHIAZOLE-2-CARBOXYLATE ETHYL IMIDAZO[2,1-B][1,3]BENZOTHIAZOLE-2-CARBOXYLATE 64951-05-9 C12H10N2O2S
Sodium benzotriazole Sodium benzotriazole 15217-42-2 C6H5N3.Na
8-NITROIMIDAZO[1,2-A]PYRIDINE 8-NITROIMIDAZO[1,2-A]PYRIDINE 52310-46-0 C7H5N3O2
2,5-Dimethoxytetrahydrofuran 2,5-Dimethoxytetrahydrofuran 696-59-3 C6H12O3
6-METHYL-3H-BENZOTHIAZOL-2-ONE 6-METHYL-3H-BENZOTHIAZOL-2-ONE 53827-53-5 C8H7NOS
5-CHLORO-1,3-DIMETHYLPYRAZOLE 5-CHLORO-1,3-DIMETHYLPYRAZOLE 54454-10-3 C5H7ClN2
2,3,3-Trimethylindolenine 2,3,3-Trimethylindolenine 1640-39-7 C11H13N
1,3-Diphenylisobenzofuran 1,3-Diphenylisobenzofuran 5471-63-6 C20H14O
[2H4]-1,2,3,4-Tetrahydro-2,4-dioxoquinazoline [2H4]-1,2,3,4-Tetrahydro-2,4-dioxoquinazoline 1258840-23-1 C8H6N2O2
5,5'-(5-aminopyrimidine-4,6-diyl)diisophthalic acid 5,5'-(5-aminopyrimidine-4,6-diyl)diisophthalic acid 1980832-02-7 C20H13N3O8
1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl-2,2,3,3-d4)-2-(octylamino)-3-(pyrrolidin-1-yl)propan-1-ol 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl-2,2,3,3-d4)-2-(octylamino)-3-(pyrrolidin-1-yl)propan-1-ol
4,4'-bis(4-methyl-1H-imidazol-1-yl)-1,1'-biphenyl 4,4'-bis(4-methyl-1H-imidazol-1-yl)-1,1'-biphenyl 1789726-52-8 C20H18N4
1H-Imidazole-2-carboxylic acid, 1-(1-methylethyl)-, ethyl ester 1H-Imidazole-2-carboxylic acid, 1-(1-methylethyl)-, ethyl ester 2017188-77-9 C9H14N2O2
Quinoxaline, 5,8-dibromo-6,7-difluoro-2-[(2-hexyldecyl)oxy]- Quinoxaline, 5,8-dibromo-6,7-difluoro-2-[(2-hexyldecyl)oxy]- 2269476-12-0 C24H34Br2F2N2O
1,3,5-Triazine, 2,4-dichloro-6-(9-phenanthrenyl)- 1,3,5-Triazine, 2,4-dichloro-6-(9-phenanthrenyl)- 2413373-12-1 C17H9Cl2N3
Ethanol, 2-[[(3aR,4S,6R,6aS)-6-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino]-5-(propylsulfonyl)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]- Ethanol, 2-[[(3aR,4S,6R,6aS)-6-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino]-5-(propylsulfonyl)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]- 1863036-51-4 C26H32F2N6O6S
2-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan -2-yl)-2H-1,2,3-triazole 2-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan -2-yl)-2H-1,2,3-triazole 2710289-98-6 C14H18BN3O2
3-Pyridinecarboxylic acid, 4-bromo-6-cyano-, methyl ester 3-Pyridinecarboxylic acid, 4-bromo-6-cyano-, methyl ester 1805183-56-5 C8H5BrN2O2
Thiazole, 4-chloro-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Thiazole, 4-chloro-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2223051-13-4 C10H15BClNO2S
2-Pyridinecarbonitrile, 6-(2-amino-4-thiazolyl)- 2-Pyridinecarbonitrile, 6-(2-amino-4-thiazolyl)- 1185317-90-1 C9H6N4S
3-Pyridinecarboxylic acid, 4-amino-6-chloro-5-fluoro- 3-Pyridinecarboxylic acid, 4-amino-6-chloro-5-fluoro- 2454491-15-5 C6H4ClFN2O2
Dibenzofuran, 1-bromo-9-chloro- Dibenzofuran, 1-bromo-9-chloro- 2179279-83-3 C12H6BrClO
2(1H)-Pyridinone, 6-methyl-4-(1-methylethyl)- 2(1H)-Pyridinone, 6-methyl-4-(1-methylethyl)- 874493-45-5 C9H13NO
4H-1,2,4-Triazol-3-amine, 4-cyclopropyl- 4H-1,2,4-Triazol-3-amine, 4-cyclopropyl- 1248414-32-5 C5H8N4
1H-1,2,3-Triazole, 5-(4-fluorophenyl)- 1H-1,2,3-Triazole, 5-(4-fluorophenyl)- 35224-98-7 C8H6FN3
Pyrrolidine, 3-(4-chlorophenyl)-3-methyl- Pyrrolidine, 3-(4-chlorophenyl)-3-methyl- 1250837-90-1 C11H14ClN
Pyrimidine, 2-(4-bromo-1H-1,2,3-triazol-1-yl)- Pyrimidine, 2-(4-bromo-1H-1,2,3-triazol-1-yl)- 2256748-88-4 C6H4BrN5
4-(2-FURYL)-6-METHYLPYRIMIDIN-2-AMINE 4-(2-FURYL)-6-METHYLPYRIMIDIN-2-AMINE 91004-63-6 C9H9N3O
2-BROMO-4,6-DIFLUORO-PYRIDINE 2-BROMO-4,6-DIFLUORO-PYRIDINE 41404-63-1 C5H2BrF2N
4-CHLORO-2-HYDROXYQUINOLINE 4-CHLORO-2-HYDROXYQUINOLINE 20146-59-2 C9H6ClNO
2-Pyrrolidinone,1-(2-bromo-4-pyridinyl)- 2-Pyrrolidinone,1-(2-bromo-4-pyridinyl)- 1142194-75-9 C9H9BrN2O
6-cyclopentylpyridin-3-ol 6-cyclopentylpyridin-3-ol 1159815-44-7 C10H13NO
5-bromo-2-(pyridin-2-yl)oxazole 5-bromo-2-(pyridin-2-yl)oxazole 1391737-93-1 C8H5BrN2O
S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid 1255936-24-3 C13H14BrN3
6-Bromo-pyridazine-3-carbonitrile 6-Bromo-pyridazine-3-carbonitrile 1027513-40-1 C5H2BrN3
2,5-Dibromo-4-fluoropyridine 2,5-Dibromo-4-fluoropyridine 1033203-46-1 C5H2Br2FN
2-(2-BroMophenyl)-9H-phenylcarbazole 2-(2-BroMophenyl)-9H-phenylcarbazole 1616607-88-5 C24H16BrN
pyrazolo[1,5-a]pyrazine pyrazolo[1,5-a]pyrazine 24973-85-1 C6H5N3
2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine1,1-dioxide 2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine1,1-dioxide 769858-09-5 C9H11NO2S
5-bromo-2-methylpyrimidine-4,6-d2 5-bromo-2-methylpyrimidine-4,6-d2 1476076-44-4 C5H3BrD2N2
6-bromo-4-methoxypyrazolo[1,5-a]pyridine-3-carbonitrile 6-bromo-4-methoxypyrazolo[1,5-a]pyridine-3-carbonitrile 1207836-10-9 C9H6BrN3O
8-Azaspiro[Bicyclo[3.2.1]Octane-3,4'-Imidazolidine]-2',5'-Dione 8-Azaspiro[Bicyclo[3.2.1]Octane-3,4'-Imidazolidine]-2',5'-Dione 77398-55-1 C9H14ClN3O2
trimorpholylmethane trimorpholylmethane 22630-09-7 C13H25N3O3
4-(2-Fluorophenyl)furan-2-boronic acid 4-(2-Fluorophenyl)furan-2-boronic acid 2096338-79-1 C10H8BFO3
4-Ethylfuran-2-boronic acid 4-Ethylfuran-2-boronic acid 2096337-32-3 C6H9BO3
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