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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-[(DIMETHYLAMINO)METHYL]IMIDAZOLE 1-[(DIMETHYLAMINO)METHYL]IMIDAZOLE 23230-39-9 C6H11N3
3-(3-Bromophenyl)-1-methyl-1H-pyrazole 3-(3-Bromophenyl)-1-methyl-1H-pyrazole 425379-68-6 C10H9BrN2
Dimiracetam Dimiracetam 126100-97-8 C6H8N2O2
NSC46839 NSC46839 14700-62-0 C10H10N2
4,5-Dihydro-2-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-imidazole mononitrate 4,5-Dihydro-2-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-imidazole mononitrate 118201-38-0 C13H17N3O3
4-Pyridinepropanenitrile,beta-hydroxy-,(betaS)-(9CI) 4-Pyridinepropanenitrile,beta-hydroxy-,(betaS)-(9CI) 676563-19-2 C8H8N2O
1H-Pyrazole-4-carbonitrile,1-methyl-(9CI) 1H-Pyrazole-4-carbonitrile,1-methyl-(9CI) 66121-71-9 C5H5N3
ETHYL 2,7-DIMETHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLATE ETHYL 2,7-DIMETHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLATE 81448-48-8 C12H14N2O2
4-Chloro-1-methylpyrazole 4-Chloro-1-methylpyrazole 35852-81-4 C4H5ClN2
2-Adamantanone oxime 2-Adamantanone oxime 4500-12-3 C10H15NO
(R)-(-)-3-FLUOROPYRROLIDINE HYDROCHLORIDE (R)-(-)-3-FLUOROPYRROLIDINE HYDROCHLORIDE 136725-55-8 C4H9ClFN
4-Bromoindole 4-Bromoindole 52488-36-5 C8H6BrN
FLAG peptide FLAG peptide 98849-88-8 C41H60N10O20
Gentioflavine Gentioflavine 18058-50-9 C10H11NO3
C-IMIDAZO[1,2-A]PYRIDIN-3-YL-METHYLAMINE C-IMIDAZO[1,2-A]PYRIDIN-3-YL-METHYLAMINE 160771-89-1 C8H9N3
5-IODO-1-METHYL-1H-PYRAZOLE 5-IODO-1-METHYL-1H-PYRAZOLE 34091-51-5 C4H5IN2
1,4,5-TRIPHENYL-1H-IMIDAZOLE-2-THIOL 1,4,5-TRIPHENYL-1H-IMIDAZOLE-2-THIOL 2349-59-9 C21H16N2S
6-Hydroxy-2-(methylsulfanyl)-4-pyrimidinecarboxylic acid 6-Hydroxy-2-(methylsulfanyl)-4-pyrimidinecarboxylic acid 6314-14-3 C6H6N2O3S
2-Phenylbenzoxazole 2-Phenylbenzoxazole 833-50-1 C13H9NO
(3R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-3-carboxylic acid (3R,4S)-1-(Tert-butoxycarbonyl)-4-phenylpyrrolidine-3-carboxylic acid 956101-09-0 C16H21NO4
6-Bromo-8-chloro-3,3-dimethyl-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione 6-Bromo-8-chloro-3,3-dimethyl-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione 1849592-09-1 C9H8BrClN2O2
6-Isopropyl-2-methylimidazo[2,1-b][1,3,4]thiadiazole-5-carboxylic acid 6-Isopropyl-2-methylimidazo[2,1-b][1,3,4]thiadiazole-5-carboxylic acid 1693935-56-6 C9H11N3O2S
Pyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione Pyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione 258282-54-1 C7H5N3O3
8-BROMO2-METHYL-[1,2,4]TRIAZOLO[1,5-A]PYRIDINE 8-BROMO2-METHYL-[1,2,4]TRIAZOLO[1,5-A]PYRIDINE 7169-96-2 C7H6BrN3
4-METHYL-1H-IMIDAZOLE-2-CARBOXYLICACID 4-METHYL-1H-IMIDAZOLE-2-CARBOXYLICACID 70631-93-5 C5H6N2O2
3-BENZOYL-7-DIETHYLAMINOCOUMARIN 3-BENZOYL-7-DIETHYLAMINOCOUMARIN 77016-78-5 C20H19NO3
2,6-DIBROMOBENZALDEHYDE 2,6-DIBROMOBENZALDEHYDE 67713-23-9 C7H4Br2O
(4R)-4-FLUORO-L-PROLINE HCL (4R)-4-FLUORO-L-PROLINE HCL 60604-36-6 C5H9ClFNO2
2-(2-bromo-4-fluorophenyl)pyrrolidine 2-(2-bromo-4-fluorophenyl)pyrrolidine 1016499-98-1 C10H11BrFN
2-bromo-4-phenyl-1,3-oxazole 2-bromo-4-phenyl-1,3-oxazole 1060816-19-4 C9H6BrNO
1-(DIETHOXYMETHYL)IMIDAZOLE 1-(DIETHOXYMETHYL)IMIDAZOLE 61278-81-7 C8H14N2O2
(R)-2-AMINOMETHYL-1-N-CBZ-PYRROLIDINE (R)-2-AMINOMETHYL-1-N-CBZ-PYRROLIDINE 1187931-23-2 C13H18N2O2
7-chloro-5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidine 7-chloro-5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidine 926230-79-7 C6H2ClF3N4
7-methylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid 7-methylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid 1016505-59-1 C8H7N3O2
8-bromo-4-chloroquinazoline 8-bromo-4-chloroquinazoline 125096-72-2 C8H4BrClN2
4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine 4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine 16372-08-0 C6H6ClN3
4,4'-dithiobis(5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile) 4,4'-dithiobis(5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile) 130755-46-3 C22H8Cl4F6N8S2
1-Benzyl-4-iodo-1H-pyrazole 1-Benzyl-4-iodo-1H-pyrazole 50877-42-4 C10H9IN2
2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine 23449-08-3 C21H14BrN3
5-AMINO-3-METHYL-1-P-TOLYLPYRAZOLE 5-AMINO-3-METHYL-1-P-TOLYLPYRAZOLE 62535-60-8 C11H13N3
3-methyl-1H-indazol-6-amine 3-methyl-1H-indazol-6-amine 79173-62-9 C8H9N3
1,2,4-TRIAZOLE 1,2,4-TRIAZOLE 736917-78-5 C2H3N3
1,2-Dioxane 1,2-Dioxane 5703-46-8 C4H8O2
4-bromo-1,5-dimethyl-1H-pyrazole 4-bromo-1,5-dimethyl-1H-pyrazole 5775-86-0 C5H7BrN2
2-Amino-7-bromobenzothiazole 2-Amino-7-bromobenzothiazole 20358-05-8 C7H5BrN2S
Ethyl 3-bromoimidazo[1,2-a]pyridine-2-carboxylate Ethyl 3-bromoimidazo[1,2-a]pyridine-2-carboxylate 143982-54-1 C10H9BrN2O2
6-PYRROLIDINO-7-DEAZAPURINE 6-PYRROLIDINO-7-DEAZAPURINE 90870-68-1 C10H12N4
1-Methyl-1H-imidazo[4,5-c]pyridine 1-Methyl-1H-imidazo[4,5-c]pyridine 5028-32-0 C7H7N3
4-Acryloylmorpholine 4-Acryloylmorpholine 5117-12-4 C7H11NO2
1-Phenyl-1H-pyrazol-3(2H)-one 1-Phenyl-1H-pyrazol-3(2H)-one 1008-79-3 C9H8N2O
2,6-DIBROMOQUINAZOLINE 2,6-DIBROMOQUINAZOLINE 161425-75-8 C8H4Br2N2
5-(4-METHOXYPHENYL)-1H-IMIDAZOL-2-AMINE 5-(4-METHOXYPHENYL)-1H-IMIDAZOL-2-AMINE 60472-20-0 C10H11N3O
2,2'-BIPYRIDINE-3,3'-DICARBONITRILE 2,2'-BIPYRIDINE-3,3'-DICARBONITRILE 136869-49-3 C12H6N4
3-Bromo-1,5-dimethylpyrazole 3-Bromo-1,5-dimethylpyrazole 5744-80-9 C5H7BrN2
5-chloropyrido[4,3-d]pyrimidine 5-chloropyrido[4,3-d]pyrimidine 1029720-78-2 C7H4ClN3
1H-PYRAZOLE-3-CARBONITRILE, 4-AMINO- 1H-PYRAZOLE-3-CARBONITRILE, 4-AMINO- 68703-67-3 C4H4N4
4-chloro-2,7-dimethylthieno[3,2-d]pyrimidine 4-chloro-2,7-dimethylthieno[3,2-d]pyrimidine 936837-34-2 C8H7ClN2S
2-tert-butyl-5H,6H,7H,8H-imidazo[1,2-a]pyridin-6-amine 2-tert-butyl-5H,6H,7H,8H-imidazo[1,2-a]pyridin-6-amine 1306606-89-2 C11H19N3
1,3-bis((1H-imidazol-1-yl)methyl)benzene 1,3-bis((1H-imidazol-1-yl)methyl)benzene 69506-92-9 C14H14N4
4-Cyano-3,5-dimethylphenylboronic acid pinacol ester 4-Cyano-3,5-dimethylphenylboronic acid pinacol ester 1111096-09-3 C15H20BNO2
4-Chloro-2H-pyrazolo[4,3-c]pyridine 4-Chloro-2H-pyrazolo[4,3-c]pyridine 1821250-10-5 C6H4ClN3
2-Bromo-1,3-benzothiazole 2-Bromo-1,3-benzothiazole 2516-40-7 C7H4BrNS
(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine (S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine 84466-85-3 C11H22N2
1-ALLYL-3 5-DIMETHYLPYRAZOLE  96 1-ALLYL-3 5-DIMETHYLPYRAZOLE 96 13369-74-9 C8H12N2
N-(2-HYDROXYBENZOYL)PYRROLIDINE  97 N-(2-HYDROXYBENZOYL)PYRROLIDINE 97 98841-68-0 C11H13NO2
1-Nitroso-1H-imidazole 1-Nitroso-1H-imidazole 1233340-45-8 C3H3N3O
7-Bromothieno[3,2-c]pyridine 7-Bromothieno[3,2-c]pyridine 1535297-40-5 C7H4BrNS
MBM morpholine derivatives MBM morpholine derivatives
1H-Pyrazol-5-ol, 1,4-dimethyl-3-(trifluoromethyl)- 1H-Pyrazol-5-ol, 1,4-dimethyl-3-(trifluoromethyl)- 656825-59-1 C6H7F3N2O
6-Bromo-2-(chloromethyl)thieno[3,2-d]pyrimidin-4(3H)-one 6-Bromo-2-(chloromethyl)thieno[3,2-d]pyrimidin-4(3H)-one 1330782-89-2 C7H4BrClN2OS
6-Bromopyrrolo[1,2-c]pyrimidine-3-carbaldehyde 6-Bromopyrrolo[1,2-c]pyrimidine-3-carbaldehyde 1352893-14-1 C8H5BrN2O
4-CHLORO-6-(METHYLTHIO)PYRIMIDINE-5-CARBONITRILE 4-CHLORO-6-(METHYLTHIO)PYRIMIDINE-5-CARBONITRILE 150807-96-8 C6H4ClN3S
6-Fluoro-2-oxindole 6-Fluoro-2-oxindole 56341-39-0 C8H6FNO
5-OXO-1-PHENYL-PYRROLIDINE-3-CARBOXYLIC ACID 5-OXO-1-PHENYL-PYRROLIDINE-3-CARBOXYLIC ACID 39629-86-2 C11H11NO3
4-CHLOROQUINAZOLIN-6-AMINE 4-CHLOROQUINAZOLIN-6-AMINE 208533-37-3 C8H6ClN3
(S)-1-Cbz-3-Aminopyrrolidine hydrochloride (S)-1-Cbz-3-Aminopyrrolidine hydrochloride 550378-39-7 C12H17ClN2O2
(O-ETHYLDITHIOCARBONATO)-S-(3-SULFOPROPYL)-ESTER, POTASSIUM SALT (O-ETHYLDITHIOCARBONATO)-S-(3-SULFOPROPYL)-ESTER, POTASSIUM SALT 93841-14-6 C6H13KO4S3
2-ETHYL-P-XYLENE 2-ETHYL-P-XYLENE 1758-88-9 C10H14
4-BROMO-1H-PYRAZOLE-3-CARBONITRILE 4-BROMO-1H-PYRAZOLE-3-CARBONITRILE 288246-16-2 C4H2BrN3
4-(1H-Imidazol-1-yl)aniline 4-(1H-Imidazol-1-yl)aniline 2221-00-3 C9H9N3
ETHYL IMIDAZO[1,2-A]PYRAZINE-2-CARBOXYLATE ETHYL IMIDAZO[1,2-A]PYRAZINE-2-CARBOXYLATE 77112-52-8 C9H9N3O2
1,3-DIDECYL-2-METHYLIMIDAZOLIUM CHLORIDE 1,3-DIDECYL-2-METHYLIMIDAZOLIUM CHLORIDE 70862-65-6 C24H47ClN2
(S)-2-(2,5-DIFLUOROPHENYL)PYRROLIDINE HYDROCHLORIDE (S)-2-(2,5-DIFLUOROPHENYL)PYRROLIDINE HYDROCHLORIDE 1443624-23-4 C10H12ClF2N
5-CHLOROMETHYL-1-PROPYL-1H-IMIDAZOLE 5-CHLOROMETHYL-1-PROPYL-1H-IMIDAZOLE 497223-15-1 C7H11ClN2
4-BROMO-5-AZAINDOLE 4-BROMO-5-AZAINDOLE 1000342-68-6 C7H5BrN2
2H-Benzotriazole, 4,7-dibromo-2-hexyl-5,6-dinitro- 2H-Benzotriazole, 4,7-dibromo-2-hexyl-5,6-dinitro- 1321184-67-1 C12H13Br2N5O4
Diroximel Fumarate Impurity 2 Diroximel Fumarate Impurity 2 2101811-41-8 C10H11NO6
2-Pyridinecarboxamide, N-(4-methoxyphenyl)- 2-Pyridinecarboxamide, N-(4-methoxyphenyl)- 14990-93-3 C13H12N2O2
3-(4-CHLOROPHENYL)PYRROLIDINE 3-(4-CHLOROPHENYL)PYRROLIDINE 120418-62-4 C10H12ClN
Spiro[acridine-9(10H),9'-[9H]thioxanthene] Spiro[acridine-9(10H),9'-[9H]thioxanthene] 1644049-46-6 C25H17NS
1-allyl-2-methyl-1H-imidazole 1-allyl-2-methyl-1H-imidazole 13173-22-3 C7H10N2
2-Pyrrolidinemethanol, 4-fluoro-1-(phenylmethyl)-, (2S,4R)- 2-Pyrrolidinemethanol, 4-fluoro-1-(phenylmethyl)-, (2S,4R)- 1318129-07-5 C12H16FNO
Methanesulfonic acid, 1,1,1-trifluoro-, 5-methyl-2-(1-methylethyl)phenyl ester Methanesulfonic acid, 1,1,1-trifluoro-, 5-methyl-2-(1-methylethyl)phenyl ester 256637-50-0 C11H13F3O3S
1,1'-(piperazine-1,4-diyldimethylene)diimidazolidine-2-thione 1,1'-(piperazine-1,4-diyldimethylene)diimidazolidine-2-thione 14764-02-4 C12H22N6S2
4-[[(2-aminoethyl)thio]methyl]-5-methylimidazole 4-[[(2-aminoethyl)thio]methyl]-5-methylimidazole 38585-67-0 C7H13N3S
5-nitro-2-(4-nitrophenyl)-1H-benzimidazole 5-nitro-2-(4-nitrophenyl)-1H-benzimidazole 1772-39-0 C13H8N4O4
2-(Chloromethyl)-4,5-difluoro-1H-benzimidazole 2-(Chloromethyl)-4,5-difluoro-1H-benzimidazole 1111269-40-9 C8H5ClF2N2
D-1,2,3,4-tetrahydronorharmane-3-carboxylic acid D-1,2,3,4-tetrahydronorharmane-3-carboxylic acid 72002-54-1 C12H12N2O2
5-Hydroxy-1-methylpyrazole 5-Hydroxy-1-methylpyrazole 33641-15-5 C4H6N2O
3-(4-BROMOPHENYL)-1H-PYRAZOLE, 97% 3-(4-BROMOPHENYL)-1H-PYRAZOLE, 97% 73387-46-9 C9H7BrN2
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