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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
1,2-PROPANEDIOL, 3-(2-NITRO-1H-IMIDAZOL-1-YL)- 1,2-PROPANEDIOL, 3-(2-NITRO-1H-IMIDAZOL-1-YL)- 13551-92-3 C6H9N3O4
6-Chloro-2-Methylpyrido[3,4-d]pyriMidin-4(1H)-one 6-Chloro-2-Methylpyrido[3,4-d]pyriMidin-4(1H)-one 1637671-24-9 C8H6ClN3O
(S)-8-chloro-2-(trifluoromethyl)-3,4-dihydro-1H-pyrimido[1,2-a]pyrimidin-6(2H)-one (S)-8-chloro-2-(trifluoromethyl)-3,4-dihydro-1H-pyrimido[1,2-a]pyrimidin-6(2H)-one 1260585-11-2 C8H7ClF3N3O
(2S,4R)-4-Chloro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (2S,4R)-4-Chloro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 317356-97-1 C11H18ClNO4
2-Fluoro-2'-Bromobiphenyl 2-Fluoro-2'-Bromobiphenyl 1554-05-8 C12H8BrF
2-AMINO-7-CHLORO-5-OXO-5H-(1)BENZOPYRANO-(2,3-B)-PYRIDINE-3-CARBONITRILE 2-AMINO-7-CHLORO-5-OXO-5H-(1)BENZOPYRANO-(2,3-B)-PYRIDINE-3-CARBONITRILE 1033202-10-6 C7H4ClFN2
1,3-bis(4-carboxyphenyl)imidazoliumchloride 1,3-bis(4-carboxyphenyl)imidazoliumchloride 1414629-40-5 C17H13ClN2O4
4-OXO-3,4-DIHYDROTHIENO[3,2-D]PYRIMIDINE-7-CARBOXYLIC ACID 4-OXO-3,4-DIHYDROTHIENO[3,2-D]PYRIMIDINE-7-CARBOXYLIC ACID 1527518-33-7 C7H4N2O3S
2-amino-5-nitro-4,6-dimethylpyridine 2-amino-5-nitro-4,6-dimethylpyridine 22934-22-1 C7H9N3O2
7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine 7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine 99951-68-5 C6H6ClN5
1-phenyl-1H-imidazo[4,5-c]pyridine 1-phenyl-1H-imidazo[4,5-c]pyridine 61532-35-2 C12H9N3
N-Hydroxy-N'-[5-(2-methyl-2-propanyl)-1H-pyrazol-3-yl]-4-nitroben zenecarboximidamide N-Hydroxy-N'-[5-(2-methyl-2-propanyl)-1H-pyrazol-3-yl]-4-nitroben zenecarboximidamide 152828-23-4 C14H17N5O3
4-Morpholinobenzaldehyde 4-Morpholinobenzaldehyde 1204-86-0 C11H13NO2
7-Iodo-2',3'-Dideoxy-7-Deaza-Guanosine 7-Iodo-2',3'-Dideoxy-7-Deaza-Guanosine 114748-67-3 C11H13IN4O3
2-Chloro-4-(1H-Pyrazol-5-Yl)Benzonitrile 2-Chloro-4-(1H-Pyrazol-5-Yl)Benzonitrile 1297537-37-1 C10H6ClN3
DE-7 DE-7 681490-93-7 C7H8ClN3O3
(2S,3S,4R)-1-tert-butyl 2-methyl 4-((3-(1,1-difluorobut-3-en-1-yl)-7-methoxyquinoxalin-2 -yl)oxy)-3-ethylpyrrolidine-1,2-dicarboxylat (2S,3S,4R)-1-tert-butyl 2-methyl 4-((3-(1,1-difluorobut-3-en-1-yl)-7-methoxyquinoxalin-2 -yl)oxy)-3-ethylpyrrolidine-1,2-dicarboxylat C26H33F2N3O6
1H-Imidazol-2-amine,1-[(6-chloro-3-pyridinyl)methyl]-4,5-dihydro-N-nitroso- 1H-Imidazol-2-amine,1-[(6-chloro-3-pyridinyl)methyl]-4,5-dihydro-N-nitroso- 131206-85-4 C9H10ClN5O
2,2'-Bioxazole, 4,4',5,5'-tetrahydro-4,4'-bis(3-methylphenyl)-, (4S,4'S)- 2,2'-Bioxazole, 4,4',5,5'-tetrahydro-4,4'-bis(3-methylphenyl)-, (4S,4'S)- 2567868-02-2 C20H20N2O2
4-Bromo-9H-fluoren-9-one 4-Bromo-9H-fluoren-9-one 4269-17-4 C13H7BrO
2-Pyridinecarboxamide,N-3-pyridinyl-(9CI) 2-Pyridinecarboxamide,N-3-pyridinyl-(9CI) 184870-10-8 C11H9N3O
1H-Pyrazole-4-carbonitrile,1,3-dimethyl-(9CI) 1H-Pyrazole-4-carbonitrile,1,3-dimethyl-(9CI) 87412-96-2 C6H7N3
1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI) 1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI) 149520-94-5 C6H9N3O2
1H-Imidazo[4,5-c]pyridine-4-carboxylicacid,4,5,6,7-tetrahydro-(9CI) 1H-Imidazo[4,5-c]pyridine-4-carboxylicacid,4,5,6,7-tetrahydro-(9CI) 777819-31-5 C7H9N3O2
1H-Isoindol-1-one,2,3-dihydro-4-methoxy-(9CI) 1H-Isoindol-1-one,2,3-dihydro-4-methoxy-(9CI) 366453-22-7 C9H9NO2
5-(beta-hydroxyethyl)-4-methylthiazole-2-carboxylic acid 5-(beta-hydroxyethyl)-4-methylthiazole-2-carboxylic acid 75113-60-9 C7H9NO3S
4-CHLORO-7-(TRIFLUOROMETHYL)QUINAZOLINE 4-CHLORO-7-(TRIFLUOROMETHYL)QUINAZOLINE 16499-65-3 C9H4ClF3N2
ETHYL 4,5-DIHYDRO-4-OXO-1H-PYRROLO[3,2-D]PYRIMIDINE-7-CARBOXYLATE ETHYL 4,5-DIHYDRO-4-OXO-1H-PYRROLO[3,2-D]PYRIMIDINE-7-CARBOXYLATE 853058-41-0 C9H9N3O3
4-TERT-BUTYL-1H-IMIDAZOL-2-AMINE 4-TERT-BUTYL-1H-IMIDAZOL-2-AMINE 82560-19-8 C7H13N3
1H,1'H-5,5'-BIBENZO[D]IMIDAZOLE 1H,1'H-5,5'-BIBENZO[D]IMIDAZOLE 3097-03-8 C14H10N4
(R)-1-BOC-3-(3-CARBOXY-PHENOXY)-PYRROLIDINE (R)-1-BOC-3-(3-CARBOXY-PHENOXY)-PYRROLIDINE 222987-19-1 C16H21NO5
5,6-DIHYDROSPIRO[CYCLOPENTA[C]PYRIDINE-7,2'-PYRROLIDINE] 5,6-DIHYDROSPIRO[CYCLOPENTA[C]PYRIDINE-7,2'-PYRROLIDINE] 463303-91-5 C11H14N2
2,4-DICHLORO-7-(TRIFLUOROMETHYL)QUINAZOLINE 2,4-DICHLORO-7-(TRIFLUOROMETHYL)QUINAZOLINE 396-02-1 C9H3Cl2F3N2
3-(6-BROMOPYRIDIN-2-YL)-6-CHLOROIMIDAZO[1,2-A]PYRIDINE 3-(6-BROMOPYRIDIN-2-YL)-6-CHLOROIMIDAZO[1,2-A]PYRIDINE 1044733-65-4 C12H7BrClN3
Imidazo[1,2-a]pyridin-2(3H)-one hydrochloride Imidazo[1,2-a]pyridin-2(3H)-one hydrochloride 52687-85-1 C7H6N2O.HCl
2,4(1H,3H)-Pyrimidinedione,1-propyl- 2,4(1H,3H)-Pyrimidinedione,1-propyl- 24466-52-2 C7H10N2O2
5H-Cyclopenta[c]pyridine-5,7(6H)-dione 5H-Cyclopenta[c]pyridine-5,7(6H)-dione 5807-19-2 C8H5NO2
3-(4-TOLYL)PYRAZOLE 3-(4-TOLYL)PYRAZOLE 59843-75-3 C10H10N2
Butanedihydrazide Butanedihydrazide 4146-43-4 C4H10N4O2
5,6-Dibromo-1H-benzotriazole 5,6-Dibromo-1H-benzotriazole 716320-92-2 C6H3Br2N3
6-(Bromomethyl)imidazo[2,1-b]-[1,3]thiazole hydrobromide 6-(Bromomethyl)imidazo[2,1-b]-[1,3]thiazole hydrobromide 330196-49-1 C6H6Br2N2S
tert-butyl cis-3-fluoro-4-hydroxypyrrolidine-1-carboxylate tert-butyl cis-3-fluoro-4-hydroxypyrrolidine-1-carboxylate 2055223-76-0 C9H16FNO3
1-Butyl-1-methylpyrrolidinium Bis(fluorosulfonyl)imide 1-Butyl-1-methylpyrrolidinium Bis(fluorosulfonyl)imide 1057745-51-3 C9H20F2N2O4S2
21H,23H-Porphine,5,10,15,20-tetra-1H-pyrazol-4-yl- 21H,23H-Porphine,5,10,15,20-tetra-1H-pyrazol-4-yl- 1849676-26-1 C32H22N12
3-(4-METHOXYPHENYL)PYRROLIDINE OXALATE 3-(4-METHOXYPHENYL)PYRROLIDINE OXALATE 96877-34-8 C13H17NO5
2,2'-Bipyridyl-5,5'-dialdehyde 2,2'-Bipyridyl-5,5'-dialdehyde 135822-72-9 C12H8N2O2
5-Chloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine 5-Chloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine 1393181-01-5 C6H5ClN4
6-methoxy-5-nitropyrimidin-4-amine 6-methoxy-5-nitropyrimidin-4-amine 73318-75-9 C5H6N4O3
4-Chlorooxazolo[4,5-c]pyridine 4-Chlorooxazolo[4,5-c]pyridine 1159829-15-8 C6H3ClN2O
4-(TERT-BUTYL)-1H-IMIDAZOL-2-AMINE HCL 4-(TERT-BUTYL)-1H-IMIDAZOL-2-AMINE HCL 1384100-95-1 C7H14ClN3
4-CHLORO-6-METHYLQUINAZOLINE 4-CHLORO-6-METHYLQUINAZOLINE 58421-79-7 C9H7ClN2
1-(2,2,2-trifluoroethyl)pyrazole-3-carbaldehyde 1-(2,2,2-trifluoroethyl)pyrazole-3-carbaldehyde 1310379-34-0 C6H5F3N2O
7-BROMO-1H-PYRROLO[3,2-C]PYRIDINE 7-BROMO-1H-PYRROLO[3,2-C]PYRIDINE 902837-42-7 C7H5BrN2
Substituted pyrazine Substituted pyrazine 2095311-51-4 C22H23N5O2
3-Chloro-2-(trifluoromethyl)-pyridine 3-Chloro-2-(trifluoromethyl)-pyridine 749875-32-9 C6H3ClF3N
Spiro[cyclohexane-1,3'(1'H)-furo[3,4-c]pyridine]-1',4-dione Spiro[cyclohexane-1,3'(1'H)-furo[3,4-c]pyridine]-1',4-dione 328233-20-1 C12H11NO3
5-(BROMOMETHYL)-3-METHYLISOXAZOLE 5-(BROMOMETHYL)-3-METHYLISOXAZOLE 36958-61-9 C5H6BrNO
4-(CHLOROMETHYL)-2-(2-FURYL)-1,3-THIAZOLE 4-(CHLOROMETHYL)-2-(2-FURYL)-1,3-THIAZOLE 13386-49-7 C8H6ClNOS
4-BROMO-6-CHLORO-1H-INDAZOLE 4-BROMO-6-CHLORO-1H-INDAZOLE 885519-03-9 C7H4BrClN2
(S)-2-N-BOC-AMINOMETHYLPYRROLIDINE (S)-2-N-BOC-AMINOMETHYLPYRROLIDINE 141774-70-1 C10H20N2O2
2-(4-FLUOROPHENYL)IMIDAZO[1,2-A]PYRIMIDINE-3-CARBALDEHYDE 2-(4-FLUOROPHENYL)IMIDAZO[1,2-A]PYRIMIDINE-3-CARBALDEHYDE 878436-47-6 C13H8FN3O
2-PHENYL-PYRROLIDINE-3-CARBOXYLIC ACID 2-PHENYL-PYRROLIDINE-3-CARBOXYLIC ACID 1241684-17-2 C11H13NO2
6-bromo-1,2-benzoxazole 6-bromo-1,2-benzoxazole 1060802-88-1 C7H4BrNO
6-Fluoro-7-azaindole 6-Fluoro-7-azaindole 898746-42-4 C7H5FN2
N-[(2S)-2-Pyrrolidinylmethyl]-trifluoromethanesulfonamide N-[(2S)-2-Pyrrolidinylmethyl]-trifluoromethanesulfonamide 782495-18-5 C6H11F3N2O2S
morpholine morpholine 99108-56-2 C4H9NO
yclopropanecarboxylic acid N-[4-[[4-chloro-6-(5-methyl-2H-pyrazol-3-ylamino)pyrimidin-2-yl]sulfanyl]phenyl]amide yclopropanecarboxylic acid N-[4-[[4-chloro-6-(5-methyl-2H-pyrazol-3-ylamino)pyrimidin-2-yl]sulfanyl]phenyl]amide 639090-55-4 C18H17ClN6OS
3-methyl-5-nitro-1H-pyrazole 3-methyl-5-nitro-1H-pyrazole 1048925-02-5 C4H5N3O2
3,4-Dithia-7H-cyclopenta[a]pentalene 3,4-Dithia-7H-cyclopenta[a]pentalene 389-58-2 C9H6S2
3-(3-BROMO-PHENYL)-ISOXAZOL-5-YLAMINE 3-(3-BROMO-PHENYL)-ISOXAZOL-5-YLAMINE 119162-52-6 C9H7BrN2O
4-(Tributylstannyl)pyrimidine 4-(Tributylstannyl)pyrimidine 332133-92-3 C16H30N2Sn
1,3-Dihydro-7-nitro-2H-imidazo[4,5-c]pyridin-2-one 1,3-Dihydro-7-nitro-2H-imidazo[4,5-c]pyridin-2-one 61719-60-6 C6H4N4O3
1-Bromo-5-phenylnaphthalene 1-Bromo-5-phenylnaphthalene 911836-38-9 C16H11Br
5-Bromo-4-tert-butylpyrimidine 5-Bromo-4-tert-butylpyrimidine 1439-08-3 C8H11BrN2
3-N-Boc-3-N-Methylaminopyrrolidine 3-N-Boc-3-N-Methylaminopyrrolidine 172478-00-1 C10H20N2O2
Naphtho[2,3-B]benzofuran-1-ylboronic acid Naphtho[2,3-B]benzofuran-1-ylboronic acid 2261008-21-1 C16H11BO3
1H-Indene, 5-[4'-[difluoro(3,4,5-trifluorophenoxy)methyl]-2,3',5'-trifluoro[1,1'-biphenyl]-4-yl]-2-ethyl-2,3-dihydro- 1H-Indene, 5-[4'-[difluoro(3,4,5-trifluorophenoxy)methyl]-2,3',5'-trifluoro[1,1'-biphenyl]-4-yl]-2-ethyl-2,3-dihydro- 1357385-66-0 C30H20F8O
2,5-Oxazolidinedione, 4-[[1-(2,4-dinitrophenyl)-1H-imidazol-4-yl]methyl]-, (4S)- 2,5-Oxazolidinedione, 4-[[1-(2,4-dinitrophenyl)-1H-imidazol-4-yl]methyl]-, (4S)- 47444-62-2 C13H9N5O7
2H-1-Benzopyran-2-one, 3-(3H-imidazo[4,5-c]pyridin-2-yl)-6-methyl- 2H-1-Benzopyran-2-one, 3-(3H-imidazo[4,5-c]pyridin-2-yl)-6-methyl- 899548-78-8 C16H11N3O2
2-(3''-Chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 2-(3''-Chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 1955546-89-0 C33H22ClN3
N-(4-(1H-imidazol-1-yl)phenyl)-4-(1H-imidazol-1-yl)-N-phenylaniline N-(4-(1H-imidazol-1-yl)phenyl)-4-(1H-imidazol-1-yl)-N-phenylaniline 1863055-77-9 C24H19N5
5-Methyl-3-isoxazolecarbonitrile 5-Methyl-3-isoxazolecarbonitrile 57351-99-2 C5H4N2O
4,7-Dibromo-5,6-difluoro-2-(2-octyldodecyl)-2H-benzo[d][1,2,3]triazole 4,7-Dibromo-5,6-difluoro-2-(2-octyldodecyl)-2H-benzo[d][1,2,3]triazole
pyridine-2-carbaldehyde-2-pyridylhydrazone pyridine-2-carbaldehyde-2-pyridylhydrazone 2215-33-0 C11H10N4
2-[1-(but-2-enyl)pent-3-enyl]pyridine 2-[1-(but-2-enyl)pent-3-enyl]pyridine 2057-42-3 C14H19N
2,4,6-tris(4-azidophenyl)pyridine 2,4,6-tris(4-azidophenyl)pyridine 1240044-76-1
Dipentaerythritol hexaacrylate Dipentaerythritol hexaacrylate 29570-58-9 C28H34O13
2-ethyl-4-nitro-1H-imidazole 2-ethyl-4-nitro-1H-imidazole 13230-03-0 C5H7N3O2
3-Methyl-4-iodopyrazole 3-Methyl-4-iodopyrazole 15802-75-2 C4H5IN2
CID 135395934 CID 135395934 2151835-07-1 C8H4F3IN2
Carbamic acid, N-[5-(1,1-dimethylethyl)-1H-imidazol-2-yl]-, 1,1-dimethylethyl ester Carbamic acid, N-[5-(1,1-dimethylethyl)-1H-imidazol-2-yl]-, 1,1-dimethylethyl ester 885962-38-9 C12H21N3O2
6-Bromoindole-3-carboxaldehyde 6-Bromoindole-3-carboxaldehyde 17826-04-9 C9H6BrNO
2-(1H-BENZOIMIDAZOL-2-YL)-ETHYLAMINE HCL 2-(1H-BENZOIMIDAZOL-2-YL)-ETHYLAMINE HCL 88704-72-7 C9H12ClN3
2-AMINO-5-BROMO-[1,3,4]THIADIAZOLE 2-AMINO-5-BROMO-[1,3,4]THIADIAZOLE 37566-39-5 C2H2BrN3S
2-Propen-1-one, 1-[(2S,5R)-2-methyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-1-piperidinyl]-, 4-methylbenzenesulfonate (1:1) 2-Propen-1-one, 1-[(2S,5R)-2-methyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-1-piperidinyl]-, 4-methylbenzenesulfonate (1:1) 2192215-81-7 C22H27N5O4S
AZETIDINE-3-CARBOXYLIC ACID HYDROCHLORIDE
AZETIDINE-3-CARBOXYLIC ACID HYDROCHLORIDE 102624-96-4 C4H8ClNO2
(10R,13S,16S)-10,13-dimethyl-16-(pyrrolidin-1-yl)-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione (10R,13S,16S)-10,13-dimethyl-16-(pyrrolidin-1-yl)-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17(2H)-dione
Zinc salt of 2-mercaptobenzimidazole benzimidazole Zinc salt of 2-mercaptobenzimidazole benzimidazole
(1'R, 3R)-1-(1'-PHENYLETHYL)-5-OXO-3-PYRROLIDINE CARBOXYLIC ACID (1'R, 3R)-1-(1'-PHENYLETHYL)-5-OXO-3-PYRROLIDINE CARBOXYLIC ACID 99735-43-0 C13H15NO3
1H-Benzimidazole-2-carboxaldehyde,4-fluoro-(9CI) 1H-Benzimidazole-2-carboxaldehyde,4-fluoro-(9CI) 615568-96-2 C8H5FN2O
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