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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-Tritylpyrazole 1-Tritylpyrazole 95163-43-2 C22H18N2
4-HYDRAZINOPYRIDINE dihydrochloride 4-HYDRAZINOPYRIDINE dihydrochloride C5H9Cl2N3
2-(tert-butoxycarbonylamino)pyridine-5-boronic acid, pinacol ester 2-(tert-butoxycarbonylamino)pyridine-5-boronic acid, pinacol ester 910462-31-6 C16H25BN2O4
6-CHLORO-1,3-DIHYDRO-2H-IMIDAZO[4,5-B]PYRIDINE-2-THIONE 6-CHLORO-1,3-DIHYDRO-2H-IMIDAZO[4,5-B]PYRIDINE-2-THIONE 19918-37-7 C6H4ClN3S
3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE 3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE 29096-60-4 C10H10N2O
2,4,7-TRICHLOROQUINAZOLINE 2,4,7-TRICHLOROQUINAZOLINE 6625-94-1 C8H3Cl3N2
2-METHYL-2-PYRROLIDIN-1-YLPROPAN-1-OL 2-METHYL-2-PYRROLIDIN-1-YLPROPAN-1-OL 101258-96-2 C8H17NO
1-(2-bromoethyl)pyrrolidine-2,5-dione 1-(2-bromoethyl)pyrrolidine-2,5-dione 55943-72-1 C6H8BrNO2
3-chloro-2-methoxybenzoic acid 3-chloro-2-methoxybenzoic acid 3260-93-3 C8H7ClO3
IMIDAZO[1,2-A]PYRIDIN-2-AMINE, 7-BROMO- IMIDAZO[1,2-A]PYRIDIN-2-AMINE, 7-BROMO- 865604-33-7 C7H6BrN3
ethyl 6-iodoH-imidazo[1,2-a]pyridine-2-carboxylate ethyl 6-iodoH-imidazo[1,2-a]pyridine-2-carboxylate 214958-32-4 C10H9IN2O2
2-(4-FLUORO-PHENYL)-IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE 2-(4-FLUORO-PHENYL)-IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE 425658-37-3 C14H9FN2O
2,3-Dibromo-4-(trifluoromethyl)pyridine 2,3-Dibromo-4-(trifluoromethyl)pyridine 1099598-01-2 C6H2Br2F3N
(R)-1-BENZYL-PYRROLIDINE-3-CARBOXYLIC ACID (R)-1-BENZYL-PYRROLIDINE-3-CARBOXYLIC ACID 1082055-65-9 C12H15NO2
ethyl 5-nitro-2,6-dioxo-3H-pyrimidine-4-carboxylate ethyl 5-nitro-2,6-dioxo-3H-pyrimidine-4-carboxylate 52047-16-2 C7H7N3O6
2-Methylindoline 2-Methylindoline 6872-06-6 C9H11N
OXO-PYRROLIDIN-1-YL-ACETIC ACID OXO-PYRROLIDIN-1-YL-ACETIC ACID 49791-37-9 C6H9NO3
4-(1H-imidazol-1-yl)pyridine 4-(1H-imidazol-1-yl)pyridine 25700-16-7 C8H7N3
2-Pyrrolidinone,3-(hydroxymethyl)-1-methyl-(9CI) 2-Pyrrolidinone,3-(hydroxymethyl)-1-methyl-(9CI) 577780-05-3 C6H11NO2
1H-Imidazole-1-aceticacid,alpha,2-dimethyl-(9CI) 1H-Imidazole-1-aceticacid,alpha,2-dimethyl-(9CI) 782414-84-0 C7H10N2O2
5-Bromo-1H-1,2,4-triazol-3-amine 5-Bromo-1H-1,2,4-triazol-3-amine 389122-08-1 C2H3BrN4
1H-Benzimidazole-2-methanol,5-chloro-1-methyl-(9CI) 1H-Benzimidazole-2-methanol,5-chloro-1-methyl-(9CI) 380177-22-0 C9H9ClN2O
2-Pyridinecarboxamide,N-2-pyrimidinyl-(9CI) 2-Pyridinecarboxamide,N-2-pyrimidinyl-(9CI) 848308-21-4 C10H8N4O
2-Bromo-N-ethyl-5-methoxybenzenamine 2-Bromo-N-ethyl-5-methoxybenzenamine 1491754-06-3 C9H12BrNO
1-(3-CHLOROPHENYL)IMIDAZOLE 1-(3-CHLOROPHENYL)IMIDAZOLE 51581-52-3 C9H7ClN2
L-Tyr-NCA L-Tyr-NCA 3415-08-5 C10H9NO4
2-Bromo-1-methyl-1H-imidazole-4-carboxylic  acid 2-Bromo-1-methyl-1H-imidazole-4-carboxylic acid 852181-03-4 C5H5BrN2O2
5-(BROMOMETHYL)OXAZOLE 5-(BROMOMETHYL)OXAZOLE 127232-42-2 C4H4BrNO
CHEMBRDG-BB 4003804 CHEMBRDG-BB 4003804 99858-80-7 C11H15NO
4-chloro-5-methoxy-2-(4-pyridinyl)pyrimidine 4-chloro-5-methoxy-2-(4-pyridinyl)pyrimidine 133661-38-8 C10H8ClN3O
5,6,7,8-Tetrahydro-imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester 5,6,7,8-Tetrahydro-imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester 91476-82-3 C9H13N3O2
ethyl 4-amino-5-methylthieno[2,3-d]pyrimidine-6-carboxylate ethyl 4-amino-5-methylthieno[2,3-d]pyrimidine-6-carboxylate 60598-74-5 C10H11N3O2S
3,3'-Bi(1H-pyrazole) 3,3'-Bi(1H-pyrazole) 2384-02-3 C6H6N4
CHEMBRDG-BB 6423830 CHEMBRDG-BB 6423830 83490-13-5 C13H10N2O2
1-CBZ-3-HYDROXYMETHYLPYRROLIDINE 1-CBZ-3-HYDROXYMETHYLPYRROLIDINE 315718-05-9 C13H17NO3
S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid 1255936-24-3 C13H14BrN3
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
2,5-Pyrrolidinedione, 1-[(4-chlorobenzoyl)oxy]- 2,5-Pyrrolidinedione, 1-[(4-chlorobenzoyl)oxy]- 68388-09-0 C11H8ClNO4
3-Pyrrolidinol, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-, (3R,5S)- 3-Pyrrolidinol, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-, (3R,5S)- 260417-94-5 C11H25NO2Si
2,3-Dibromo-5,6,7,8-tetrahydroimidazo-[1,2-a]pyridine 2,3-Dibromo-5,6,7,8-tetrahydroimidazo-[1,2-a]pyridine 156817-73-1 C7H8Br2N2
4-Chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine 4-Chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine 870706-47-1 C9H10ClN3
Thiazolo[4,5-d]pyrimidin-2-amine, 7-chloro-5-[[(1S)-1-phenylethyl]thio]- Thiazolo[4,5-d]pyrimidin-2-amine, 7-chloro-5-[[(1S)-1-phenylethyl]thio]- 911820-08-1 C13H11ClN4S2
2,4,6-tris(4-pyrazol-1-yl)-1,3,5-triazine 2,4,6-tris(4-pyrazol-1-yl)-1,3,5-triazine 27257-90-5 C12H9N9
Atogepant (MK-8031) Atogepant (MK-8031) 1374248-81-3 C29H23F6N5O3
4-Phenyl-2(3H)-thiazolone 4-Phenyl-2(3H)-thiazolone 3884-31-9 C9H7NOS
6-Nitroindazole 6-Nitroindazole 7597-18-4 C7H5N3O2
8-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyridine 8-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyridine 1206981-68-1 C8H4BrF3N2
5-CYCLOPROPYL-2H-PYRAZOL-3-YLAMINE 5-CYCLOPROPYL-2H-PYRAZOL-3-YLAMINE 175137-46-9 C6H9N3
5-FLUORO-1H-BENZIMIDAZOLE-2-AMINE 5-FLUORO-1H-BENZIMIDAZOLE-2-AMINE 30486-73-8 C7H6FN3
1,3-BIS(4-CHLOROPHENYL)IMIDAZOLIUM CHLORIDE 1,3-BIS(4-CHLOROPHENYL)IMIDAZOLIUM CHLORIDE 141556-46-9 C15H11Cl3N2
4-bromo-2,1,3-benzothiadiazole 4-bromo-2,1,3-benzothiadiazole 22034-13-5 C6H3BrN2S
2-Chloro-6-fluorobenzothiazole 2-Chloro-6-fluorobenzothiazole 399-74-6 C7H3ClFNS
PPT PPT 263717-53-9 C24H22N2O3
6-FLUOROPYRIDINE-2-SULFONYL CHLORIDE 6-FLUOROPYRIDINE-2-SULFONYL CHLORIDE 128583-07-3 C5H3ClFNO2S
BENZO[4,5]IMIDAZO[1,2-A][1,3,5]TRIAZIN-2-YLAMINE BENZO[4,5]IMIDAZO[1,2-A][1,3,5]TRIAZIN-2-YLAMINE 61678-05-5 C9H7N5
METHYL 2-(METHYLTHIO)PYRIMIDINE-4-CARBOXYLATE METHYL 2-(METHYLTHIO)PYRIMIDINE-4-CARBOXYLATE 64224-67-5 C7H8N2O2S
1-[(3S)-3-PYRROLIDINYL]-PIPERIDINE DIHYDROCHLORIDE 1-[(3S)-3-PYRROLIDINYL]-PIPERIDINE DIHYDROCHLORIDE 917505-12-5 C9H19ClN2
4-AMINO-5-BROMO-6-ETHOXYPICOLINIC ACID 4-AMINO-5-BROMO-6-ETHOXYPICOLINIC ACID 1057260-48-6 C8H9BrN2O3
5-bromo-1H-pyrrolo[2,3-c]
pyridine-2-carboxylic acid 5-bromo-1H-pyrrolo[2,3-c] pyridine-2-carboxylic acid 800401-71-2 C8H5BrN2O2
2,4-Dichloro-7-cyanoquinazoline 2,4-Dichloro-7-cyanoquinazoline 864292-40-0 C9H3Cl2N3
Pyrrolidine,  2-[bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl]-,  (2R)- Pyrrolidine, 2-[bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl]-, (2R)- 908303-26-4 C24H23F12NOSi
2,4,6-Trichloro-pyrido[3,2-d]pyrimidine 2,4,6-Trichloro-pyrido[3,2-d]pyrimidine 1036738-12-1 C7H2Cl3N3
3-Amino-1-methylpiperidine dihydrochloride 3-Amino-1-methylpiperidine dihydrochloride 894808-73-2 C6H15ClN2
(3S,4R)-1-benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid (3S,4R)-1-benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid 80909-49-5 C18H18FNO2
(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide (R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide 473727-83-2 C21H23N3O5
1-Pyrrolidinecarboxaldehyde, 2-oxo- 1-Pyrrolidinecarboxaldehyde, 2-oxo- 40321-44-6 C5H7NO2
6-chloropyrido[3,2-d]pyrimidin-4(3H)-one 6-chloropyrido[3,2-d]pyrimidin-4(3H)-one 171178-33-9 C7H4ClN3O
4-broMo-2-(2,6-dichlorophenyl)-7-fluoro-1H-iMidazo[4,5-c]pyridine 4-broMo-2-(2,6-dichlorophenyl)-7-fluoro-1H-iMidazo[4,5-c]pyridine 1334411-83-4 C12H5BrCl2FN3
5-BroMo-2-chloro-6-MethylpyriMidin-4-aMine 5-BroMo-2-chloro-6-MethylpyriMidin-4-aMine 54093-23-1 C5H5BrClN3
3-(BroMoMethyl)-1H-pyrrolo[2,3-b]pyridine 3-(BroMoMethyl)-1H-pyrrolo[2,3-b]pyridine 1174007-40-9 C8H7BrN2
2-Chloro-4-(trifluoromethyl)nicotinonitrile 2-Chloro-4-(trifluoromethyl)nicotinonitrile 896447-72-6 C7H2ClF3N2
3-fluoro-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine hydrochloride 3-fluoro-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine hydrochloride 1346808-65-8 C7H8ClFN2
5-Fluoro-3,4-dihydro-2,4-dioxo-1(2H)-PyriMidineacetic Acid 5-Fluoro-3,4-dihydro-2,4-dioxo-1(2H)-PyriMidineacetic Acid 56059-30-4 C6H5FN2O4
TribroMocyanuric acid TribroMocyanuric acid 17497-85-7 C3Br3N3O3
2-PYRROLIDIN-2-YLPYRIDINE 2-PYRROLIDIN-2-YLPYRIDINE 22083-78-9 C9H12N2
1-(3-HydroxyMethyl-pyrrolidin-1-yl)-ethanone 1-(3-HydroxyMethyl-pyrrolidin-1-yl)-ethanone 191347-96-3 C7H13NO2
Isopropyl-(4-Methyl-pyriMidin-2-yl)-aMine Isopropyl-(4-Methyl-pyriMidin-2-yl)-aMine 1341073-92-4 C8H13N3
Ethyl 4-Methyl-2-(Methylthio)-6-oxo-1,6-dihydropyriMidine-5-carboxylate Ethyl 4-Methyl-2-(Methylthio)-6-oxo-1,6-dihydropyriMidine-5-carboxylate 344361-90-6 C9H12N2O3S
5-(2-AMinopropyl)indole 5-(2-AMinopropyl)indole 3784-30-3 C11H14N2
IMidazo[1,2-a]pyridin-8-aMine, 7-broMo- IMidazo[1,2-a]pyridin-8-aMine, 7-broMo- 1357945-44-8 C7H6BrN3
1,3-Pyrrolidinedicarboxylic acid, 4-oxo-, 1-(1,1-diMethylethyl) 3-Methyl ester 1,3-Pyrrolidinedicarboxylic acid, 4-oxo-, 1-(1,1-diMethylethyl) 3-Methyl ester 194924-95-3 C11H17NO5
tert-butyl octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate tert-butyl octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate 1211586-14-9 C12H22N2O2
(S)-4-Oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid (S)-4-Oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid 1190392-22-3 C8H8N2O3
1-Methyl-5-oxo-L-Proline 1-Methyl-5-oxo-L-Proline 52574-06-8 C6H9NO3
3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione 1239986-50-5 C23H19N3O2
5-chloro-7-(3,4-diMethoxyphenyl)iMidazo[1,2-c]pyriMidine 5-chloro-7-(3,4-diMethoxyphenyl)iMidazo[1,2-c]pyriMidine 371171-20-9 C14H12ClN3O2
BenzaMide, N-[2-[[(3R,4R)-1-[cis-4-(1,3-benzodioxol-5-yl)-4-hydroxycyclohexyl]-4-ethoxy-3-pyrrolidinyl]aMino]-2-oxoethyl]-3-(trifluoroMethyl)-, rel- BenzaMide, N-[2-[[(3R,4R)-1-[cis-4-(1,3-benzodioxol-5-yl)-4-hydroxycyclohexyl]-4-ethoxy-3-pyrrolidinyl]aMino]-2-oxoethyl]-3-(trifluoroMethyl)-, rel- 1285539-85-6 C29H34F3N3O6
2,4-Dichloro-6-isopropyl-5,6-dihydropyrrolo[3,4-d]pyriMidin-7-one 2,4-Dichloro-6-isopropyl-5,6-dihydropyrrolo[3,4-d]pyriMidin-7-one 1079649-94-7 C9H9Cl2N3O
(2-BENZOTHIAZOLYLTHIO)ACETIC ACID (2-BENZOTHIAZOLYLTHIO)ACETIC ACID 6295-57-4 C9H7NO2S2
3-[[3,5-bis(trifluoroMethyl)phenyl]aMino]-4-[[(1S,2S)-2-(1-pyrrolidinyl)cyclohexyl]aMino]- 3-[[3,5-bis(trifluoroMethyl)phenyl]aMino]-4-[[(1S,2S)-2-(1-pyrrolidinyl)cyclohexyl]aMino]- 1211565-10-4 C22H23F6N3O2
2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3R,4R)-rel- 2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3R,4R)-rel- 905853-99-8 C23H19N3O2
CyclopentaneMethanol, 4-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-7-yl)-2-hydroxy-, (1S,2S,4R)- CyclopentaneMethanol, 4-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-7-yl)-2-hydroxy-, (1S,2S,4R)- 1113025-27-6 C12H14ClN3O2
1-Ethyl-1H-iMidazole-5-carboxylic acid 1-Ethyl-1H-iMidazole-5-carboxylic acid 71925-11-6 C6H8N2O2
6-IODO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 6-IODO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 478040-59-4 C8H5IN2O2
2,6-Bis[(4S)-phenyl-2-oxazolin-2-yl]pyridine 2,6-Bis[(4S)-phenyl-2-oxazolin-2-yl]pyridine 174500-20-0 C23H19N3O2
STYRENE MALEIC ANHYDRIDE COPOLYMER STYRENE MALEIC ANHYDRIDE COPOLYMER 9011-13-6 (C8H8.C4H2O3)x
Benzo[b]naphtho[2,1-d]furan, 8-bromo- Benzo[b]naphtho[2,1-d]furan, 8-bromo- 1627917-20-7 C16H9BrO
4-(2-METHYLIMIDAZOL-1-YLMETHYL)PHENYLAMINE 4-(2-METHYLIMIDAZOL-1-YLMETHYL)PHENYLAMINE 772311-98-5 C11H13N3
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