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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-Pyridinecarboxamide,2-amino-5-bromo-N-cyclopropyl-(9CI) 3-Pyridinecarboxamide,2-amino-5-bromo-N-cyclopropyl-(9CI) 781642-04-4 C9H10BrN3O
2,6-Pyridinediamine,1-oxide(9CI) 2,6-Pyridinediamine,1-oxide(9CI) 146538-81-0 C5H7N3O
3-Chloro-1,2,4-triazole 3-Chloro-1,2,4-triazole 6818-99-1 C2H2ClN3
N-Methyl-Cyclazodone N-Methyl-Cyclazodone
(R)-(-)-1-Benzyl-3-aminopyrrolidine (R)-(-)-1-Benzyl-3-aminopyrrolidine 114715-39-8 C11H16N2
Poly urethane Poly urethane 51852-81-4 C16H22N2O5
3,5-diphenyloxazole 3,5-diphenyloxazole 2039-49-8 C15H11NO
1-(4-Bromophenyl)-1H-pyrazole 1-(4-Bromophenyl)-1H-pyrazole 13788-92-6 C9H7BrN2
N,N-diethyl-3-methyl-4-[(5-nitro-1,3-thiazol-2-yl)diazenyl]aniline N,N-diethyl-3-methyl-4-[(5-nitro-1,3-thiazol-2-yl)diazenyl]aniline 70693-64-0 C14H17N5O2S
(S)-N-Phenyl-2-pyrrolidinecarboxamide (S)-N-Phenyl-2-pyrrolidinecarboxamide 64030-43-9 C11H14N2O
2,4-DICHLORO-6-FLUOROQUINAZOLINE 2,4-DICHLORO-6-FLUOROQUINAZOLINE 134517-57-0 C8H3Cl2FN2
2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile
2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile 775351-54-7 C14H18BNO2
6-Bromo-2-iodoquinazoline 6-Bromo-2-iodoquinazoline 882670-93-1 C8H4BrIN2
4-Trifluoromethyl-pyridine-2-carbaldehyde 4-Trifluoromethyl-pyridine-2-carbaldehyde 132470-83-8 C7H4F3NO
4-(Trifluoromethyl)pyridine-2-thiol 4-(Trifluoromethyl)pyridine-2-thiol 121307-79-7 C6H4F3NS
2H-PYRIMIDO[1,2-B]PYRIDAZIN, 2-CHLORO-7,8-DIMETHYL- 2H-PYRIMIDO[1,2-B]PYRIDAZIN, 2-CHLORO-7,8-DIMETHYL- 17412-26-9 C8H8ClN3
6-Aminoindazole 6-Aminoindazole 6967-12-0 C7H7N3
Azacyclotridecan-2-one Azacyclotridecan-2-one 947-04-6 C12H23NO
(S)-4,5-DIHYDRO-2-(2-((S)-4,5-DIHYDRO-4-ISOPROPYLOXAZOL-2-YL)PROPAN-2-YL)-4-ISOPROPYLOXAZOLE (S)-4,5-DIHYDRO-2-(2-((S)-4,5-DIHYDRO-4-ISOPROPYLOXAZOL-2-YL)PROPAN-2-YL)-4-ISOPROPYLOXAZOLE 131833-92-6 C15H26N2O2
3-Hydroxy-2-bromo-6-trifluoromethylpyridine 3-Hydroxy-2-bromo-6-trifluoromethylpyridine 1211526-50-9 C6H3BrF3NO
2-chloro-3-(trifluoromethyl)pyridine 1-oxide 2-chloro-3-(trifluoromethyl)pyridine 1-oxide 164464-57-7 C6H3ClF3NO
5-bromo-4-(2-fluoropropan-2-yl)pyrimidine 5-bromo-4-(2-fluoropropan-2-yl)pyrimidine 1823944-93-9 C7H8BrFN2
3-bromo-1-methyl-1H-Pyrrolo[2,3-c]pyridine 3-bromo-1-methyl-1H-Pyrrolo[2,3-c]pyridine 956003-06-8 C8H7BrN2
exo-8-boc-8-azabicyclo[3.2.1]octan-2-amine exo-8-boc-8-azabicyclo[3.2.1]octan-2-amine 1408074-65-6 C12H22N2O2
1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazole 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazole 1607838-14-1 C16H21BN2O2
ETHYL 8-CHLORO-6-(TRIFLUOROMETHYL)IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLATE ETHYL 8-CHLORO-6-(TRIFLUOROMETHYL)IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLATE 353258-31-8 C11H8ClF3N2O2
7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline 7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline 1083325-87-4 C12H9BrN4
9-[1,1'-Biphenyl]-3-yl-9'-[1,1'-biphenyl]-4-yl-3,3'-bi-9H-carbazole 9-[1,1'-Biphenyl]-3-yl-9'-[1,1'-biphenyl]-4-yl-3,3'-bi-9H-carbazole 1643479-47-3 C48H32N2
N,N-Dimethyl-phosphoramidochloridic acid [(2S,6R)-6-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-4-(triphenylmethyl)-2-morpholinyl]methyl ester N,N-Dimethyl-phosphoramidochloridic acid [(2S,6R)-6-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-4-(triphenylmethyl)-2-morpholinyl]methyl ester 956139-30-3 C31H34ClN4O5P
6-chloro-1,3-dihydro-5-iodo-2H-Imidazo[4,5-b]pyridine-2-thione 6-chloro-1,3-dihydro-5-iodo-2H-Imidazo[4,5-b]pyridine-2-thione 1394373-25-1 C6H3ClIN3S
1-bromo-4-(trifluoromethyl)cyclohexane 1-bromo-4-(trifluoromethyl)cyclohexane 30129-20-5 C7H10BrF3
5-Trifluoromethyl-imidazo[1,2-a]pyridine-2-carbaldehyde 5-Trifluoromethyl-imidazo[1,2-a]pyridine-2-carbaldehyde 881841-26-5 C9H5F3N2O
Morpholine,4,4'-(phenylphosphinylidene)bis- (9CI) Morpholine,4,4'-(phenylphosphinylidene)bis- (9CI) 37624-67-2 C14H21N2O3P
5-(3-Nitrophenyl)-1-[3-(trifluoromethyl)phenyl]-1H-imidazole-2-thiol 5-(3-Nitrophenyl)-1-[3-(trifluoromethyl)phenyl]-1H-imidazole-2-thiol 1105189-24-9 C16H10F3N3O2S
Chloro[1,3-bis(adamantyl)2H-imidazol-2-ylidene]gold(I) Chloro[1,3-bis(adamantyl)2H-imidazol-2-ylidene]gold(I) 852445-88-6 C23H32AuClN2
1-(2-chloropyrimidin-4-yl)-3-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 1-(2-chloropyrimidin-4-yl)-3-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 1835668-75-1 C12H9ClN4O
1,1'-(benzene-1,4-diyldimethylene)-bis(3,5-dimethyl-1H-pyrazole) 1,1'-(benzene-1,4-diyldimethylene)-bis(3,5-dimethyl-1H-pyrazole) 172606-22-3 C18H22N4
Methyl 2-oxindole-4-carboxylate Methyl 2-oxindole-4-carboxylate 90924-46-2 C10H9NO3
ETHYL 5-AMINO-1-(TERT-BUTYL)-1H-IMIDAZOLE-4-CARBOXYLATE ETHYL 5-AMINO-1-(TERT-BUTYL)-1H-IMIDAZOLE-4-CARBOXYLATE 76182-23-5 C10H17N3O2
2-CHLORO-4-BENZYLAMINO-5-METHYLPYRIMIDINE 2-CHLORO-4-BENZYLAMINO-5-METHYLPYRIMIDINE 91396-13-3 C12H12ClN3
(R)-5-AMINOMETHYL-PYRROLIDIN-2-ONE (R)-5-AMINOMETHYL-PYRROLIDIN-2-ONE 173336-98-6 C5H10N2O
4-bromothieno[3,2-d]pyrimidine 4-bromothieno[3,2-d]pyrimidine 16285-70-4 C6H3BrN2S
(S,S)-(-)-2,2'-ISOPROPYLIDENEBIS(4-TERT-BUTYL-2-OXAZOLINE) (S,S)-(-)-2,2'-ISOPROPYLIDENEBIS(4-TERT-BUTYL-2-OXAZOLINE) 131833-93-7 C17H30N2O2
2,6-Dimethylbenzyl chloride 2,6-Dimethylbenzyl chloride 5402-60-8 C9H11Cl
4-(3-BROMO-PHENYL)-THIAZOL-2-YLAMINE 4-(3-BROMO-PHENYL)-THIAZOL-2-YLAMINE 105512-81-0 C9H7BrN2S
7-(4-tert-Butylphenyl)-2-methyl-1H-indene 7-(4-tert-Butylphenyl)-2-methyl-1H-indene 245653-52-5 C20H22
6-Methylimidazo[2,1-b]thiazole 6-Methylimidazo[2,1-b]thiazole 3835-41-4 C6H6N2S
2,4-Dimethylquinazoline 2,4-Dimethylquinazoline 703-63-9 C10H10N2
4-Methyl-6-ethoxypyrimidine-2-amine 4-Methyl-6-ethoxypyrimidine-2-amine 7749-48-6 C7H11N3O
5-NITRO-1H-BENZOIMIDAZOLE-2-CARBOXYLIC ACID 5-NITRO-1H-BENZOIMIDAZOLE-2-CARBOXYLIC ACID 73903-18-1 C8H5N3O4
1-ALLYLPYRIMIDINE-2,4(1H,3H)-DIONE 1-ALLYLPYRIMIDINE-2,4(1H,3H)-DIONE 25855-26-9 C7H8N2O2
2,4-DICHLORO-7-BROMOQUINAZOLINE 2,4-DICHLORO-7-BROMOQUINAZOLINE 959237-68-4 C8H3BrCl2N2
8-METHYLIMIDAZO[1,2-A]PYRIDINE 8-METHYLIMIDAZO[1,2-A]PYRIDINE 874-10-2 C8H8N2
3-Bromo-5-chloroimidazo[1,2-a]pyridine 3-Bromo-5-chloroimidazo[1,2-a]pyridine 1260656-94-7 C7H4BrClN2
1-(3-METHYLPHENYL)-2-OXO-3-PYRROLIDINEC& 1-(3-METHYLPHENYL)-2-OXO-3-PYRROLIDINEC& 618070-31-8 C12H13NO3
(S)-4-bromo-1-(pyrrolidin-3-yl)-1H-pyrazole hydrochloride (S)-4-bromo-1-(pyrrolidin-3-yl)-1H-pyrazole hydrochloride 2828444-32-0 C7H11BrClN3
2-Pyridinecarboximidic acid, 2-methylhydrazide 2-Pyridinecarboximidic acid, 2-methylhydrazide 28819-35-4 C7H10N4
(R)-4-iodo-1-(pyrrolidin-3-yl)-1H-pyrazole (R)-4-iodo-1-(pyrrolidin-3-yl)-1H-pyrazole
Pyrrolo[1,2-c]pyrimidine-3-carboxylic acid (9CI) Pyrrolo[1,2-c]pyrimidine-3-carboxylic acid (9CI) 251102-27-9 C8H6N2O2
Pyrrolidine, 2-(2-fluorophenyl)-4-methyl- (9CI) Pyrrolidine, 2-(2-fluorophenyl)-4-methyl- (9CI) 603068-40-2 C11H14FN
1H-Imidazole-1-propanoic acid, α-cyclopropyl-α-(methylamino)- 1H-Imidazole-1-propanoic acid, α-cyclopropyl-α-(methylamino)- 1338993-61-5 C10H15N3O2
1-Pyrrolidinecarboxylic acid, 3-(difluoromethyl)-4-hydroxy-, 1,1-dimethylethyl ester, (3R,4S)-rel- 1-Pyrrolidinecarboxylic acid, 3-(difluoromethyl)-4-hydroxy-, 1,1-dimethylethyl ester, (3R,4S)-rel- 2368911-11-7 C10H17F2NO3
2-Pyrrolidinemethanol, 1-methyl-4-(trifluoromethyl)-, (2S,4R)- 2-Pyrrolidinemethanol, 1-methyl-4-(trifluoromethyl)-, (2S,4R)- 2621932-86-1 C7H12F3NO
2,4-diamino-6-chloropyrimidine-1-oxide 2,4-diamino-6-chloropyrimidine-1-oxide
6-bromo-2-fluoro-3-(3-(pyrrolidin-1-yl)propoxy)benzonitrile 6-bromo-2-fluoro-3-(3-(pyrrolidin-1-yl)propoxy)benzonitrile
5-Bromo-quinazoline 5-Bromo-quinazoline 958452-00-1 C8H5BrN2
9-(biphenyl-3-yl)-carbazol-3-yl boronic acid 9-(biphenyl-3-yl)-carbazol-3-yl boronic acid 1416814-68-0 C24H18BNO2
1-methyl-4-aminoimidazole-2-carboxylic acid methyl ester hydrochloride 1-methyl-4-aminoimidazole-2-carboxylic acid methyl ester hydrochloride 480433-71-4 C6H10ClN3O2
5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide 1272353-82-8 C25H20N6O2S
1-Pyrrolidinecarboxylic acid, 2-[(5-bromo-1H-indol-3-yl)carbonyl]-, phenylmethyl ester, (S)- 1-Pyrrolidinecarboxylic acid, 2-[(5-bromo-1H-indol-3-yl)carbonyl]-, phenylmethyl ester, (S)- 199659-03-5 C21H19BrN2O3
3-Bromo-6-(trifluoromethyl)pyridine-2-carbaldehyde 3-Bromo-6-(trifluoromethyl)pyridine-2-carbaldehyde 1227573-28-5 C7H3BrF3NO
1H-Imidazol-4-ylmethylamine dihydrochloride 1H-Imidazol-4-ylmethylamine dihydrochloride 72631-80-2 C4H9Cl2N3
tert-butyl azetidin-3-ylmethyl(methyl)carbamate tert-butyl azetidin-3-ylmethyl(methyl)carbamate 1053655-53-0 C10H20N2O2
1-tert-Butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 1-tert-Butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 1256359-15-5 C13H23BN2O2
N-(Furan-2-ylmethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine N-(Furan-2-ylmethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine 1218790-00-1 C15H20BN3O3
3-bromo-6-methoxyimidazo[1,2-a]pyridine 3-bromo-6-methoxyimidazo[1,2-a]pyridine 1044733-59-6 C8H7BrN2O
6-methyl-1H-benzimidazol-7-amine(SALTDATA: FREE) 6-methyl-1H-benzimidazol-7-amine(SALTDATA: FREE) 935873-39-5 C8H9N3
5-(3-fluorophenyl)pyridine-3-carbonitrile 5-(3-fluorophenyl)pyridine-3-carbonitrile 1214373-90-6 C12H7FN2
5-(forMylaMino)-1H-pyrazole-4-carboxaMide 5-(forMylaMino)-1H-pyrazole-4-carboxaMide 22407-20-1 C5H6N4O2
2-AMino-1,4,5,6-tetrahydropyriMidine Hydrochloride 2-AMino-1,4,5,6-tetrahydropyriMidine Hydrochloride 26893-39-0 C4H10ClN3
1H-IMidazole, 4,5-dihydro-2-(4-Methylphenyl)- 1H-IMidazole, 4,5-dihydro-2-(4-Methylphenyl)- 13623-58-0 C10H12N2
(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile (R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile 1146629-84-6 C17H26BN3O2
2,3-Bis(benzyloxy)pyridine 2,3-Bis(benzyloxy)pyridine 1228665-98-2 C19H17NO2
6-Chloro-5-nitroimidazo[2,1-b][1,3]thiazole 6-Chloro-5-nitroimidazo[2,1-b][1,3]thiazole 23576-89-8 C5H2ClN3O2S
4-CHLORO-3H-IMIDAZO[4,5-C]PYRIDINE 4-CHLORO-3H-IMIDAZO[4,5-C]PYRIDINE 81053-66-9 C6H4ClN3
4-BROMO-6-FLUORO (1H)INDAZOLE 4-BROMO-6-FLUORO (1H)INDAZOLE 885520-35-4 C7H4BrFN2
1-tert-butyl-5-chloro-1H-pyrazole-4-carbonitrile 1-tert-butyl-5-chloro-1H-pyrazole-4-carbonitrile 1050619-87-8 C8H10ClN3
Pd(IPr)(acac)Cl Pd(IPr)(acac)Cl 868705-03-7 C32H43ClN2O2Pd
1-(DiMethylsulfaMoyl)pyrazole 1-(DiMethylsulfaMoyl)pyrazole 133228-21-4 C5H9N3O2S
S-2-(CBZ-AMINOMETHYL)PYRROLIDINE-HCl S-2-(CBZ-AMINOMETHYL)PYRROLIDINE-HCl 1033245-45-2 C13H19ClN2O2
6-BroMo-2-chloro-8-fluoroquinazoline 6-BroMo-2-chloro-8-fluoroquinazoline 953039-25-3 C8H3BrClFN2
(3R,5R)-5-Methylpyrrolidin-3-ol hydrochloride (3R,5R)-5-Methylpyrrolidin-3-ol hydrochloride 857651-11-7 C5H12ClNO
2-aMino-3-(2-Methoxybenzoyl)-5-broMopyridine 2-aMino-3-(2-Methoxybenzoyl)-5-broMopyridine 875639-76-2 C13H11BrN2O2
(3R)-1-Methyl-3-PyrrolidinaMine hydrochloride (3R)-1-Methyl-3-PyrrolidinaMine hydrochloride 403712-80-1 C5H13ClN2
IMidazo[1,2-a]pyridine, 6-fluoro-2-phenyl- IMidazo[1,2-a]pyridine, 6-fluoro-2-phenyl- 1126635-20-8 C13H9FN2
(1H,1H,2H,2H-PERFLUORO-N-HEXYL)METHYLDICHLORO-SILANE (1H,1H,2H,2H-PERFLUORO-N-HEXYL)METHYLDICHLORO-SILANE 38436-16-7 C7H7Cl2F9Si
(2R,4S)-1-FMoc-4-BOC-aMino Pyrrolidine-2-carboxylic acid (2R,4S)-1-FMoc-4-BOC-aMino Pyrrolidine-2-carboxylic acid 1820570-42-0 C25H28N2O6
1-Ethyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide 1-Ethyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide 223436-99-5 C9H16F6N2O4S2
2-(3,4-diMethoxybenzyl)-7-((2S,3S)-2-hydroxy-6-phenylhexan-3-yl)-5-MethyliMidazo[1,5-f][1,2,4]triazin-4(3H)-one 2-(3,4-diMethoxybenzyl)-7-((2S,3S)-2-hydroxy-6-phenylhexan-3-yl)-5-MethyliMidazo[1,5-f][1,2,4]triazin-4(3H)-one 439083-91-7 C27H32N4O4
2-broMo-5-iodoiMidazo[2,1-b]thiazole 2-broMo-5-iodoiMidazo[2,1-b]thiazole 1379307-48-8 C5H2BrIN2S
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