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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
Imidazo[1,2-a]pyridine, 3-bromo-2-(4-
fluorophenyl)- Imidazo[1,2-a]pyridine, 3-bromo-2-(4- fluorophenyl)- 158958-74-8 C13H8BrFN2
1,2-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazole 1,2-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-imidazole 2223050-13-1 C11H19BN2O2
phenyl (R)-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)carbamate phenyl (R)-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)carbamate 2135871-21-3 C23H19F2N5O2
2'-(Methylthio)-7',8'-dihydro-6'H-spiro[cyclohexane-1,9'-pyrazino[1',2':1,5]pyrrolo[2,3-d]pyrimidin]-6'-one 2'-(Methylthio)-7',8'-dihydro-6'H-spiro[cyclohexane-1,9'-pyrazino[1',2':1,5]pyrrolo[2,3-d]pyrimidin]-6'-one 2170747-00-7 C15H18N4OS
6,7-Dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol 6,7-Dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol 1557178-09-2 C6H8N2O2
1H-Imidazole, 1,1'-(oxydi-4,1-phenylene)bis- 1H-Imidazole, 1,1'-(oxydi-4,1-phenylene)bis- 13120-43-9 C18H14N4O
1H-Imidazole, 1,1'-(2,5-dimethyl-1,4-phenylene)bis- 1H-Imidazole, 1,1'-(2,5-dimethyl-1,4-phenylene)bis- 1347702-73-1 C14H14N4
4,6- diisopropylpyrimidin-5-amine 4,6- diisopropylpyrimidin-5-amine 2168417-89-6 C10H17N3
4,4'-Bi-1H-pyrazole 4,4'-Bi-1H-pyrazole 25240-33-9 C6H6N4
2,4,6-trichlorobenzimidazole 2,4,6-trichlorobenzimidazole 142356-47-6 C7H3Cl3N2
4-[(S)-4-Boc-2-methyl-1-piperazinyl]-6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(2-isopropyl-4-methyl-3-pyridyl)pyrido[2,3-d]pyrimidin-2(1H)-one 4-[(S)-4-Boc-2-methyl-1-piperazinyl]-6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(2-isopropyl-4-methyl-3-pyridyl)pyrido[2,3-d]pyrimidin-2(1H)-one 2252403-85-1 C32H36F2N6O4
2,2'-Bioxazole, 4,4'-bis(1,1-dimethylethyl)-4,4',5,5'-tetrahydro-, (4S,4'S)- 2,2'-Bioxazole, 4,4'-bis(1,1-dimethylethyl)-4,4',5,5'-tetrahydro-, (4S,4'S)- 135565-31-0 C14H24N2O2
7-methyl-2H,3H,4H-pyrido[1,2-a]pyrimidin-3-ol hydrochloride 7-methyl-2H,3H,4H-pyrido[1,2-a]pyrimidin-3-ol hydrochloride 6056-42-4 C9H12N2O.HCl
(2S,3S)-3-Hydroxypyrrolidine-2-carboxamide hydrochloride (2S,3S)-3-Hydroxypyrrolidine-2-carboxamide hydrochloride 426844-45-3 C5H11ClN2O2
(5,6,7,8-Tetrahydroimidazo[1,2-a]pyridin-7-yl)methanamine dihydrochloride (5,6,7,8-Tetrahydroimidazo[1,2-a]pyridin-7-yl)methanamine dihydrochloride 1803583-23-4 C8H14ClN3
7-Methoxy-5-(methylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine 7-Methoxy-5-(methylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine 1350563-51-7 C6H7N5OS
Imidazo[2,1-b]thiazol-5-ylmethanamine Imidazo[2,1-b]thiazol-5-ylmethanamine 933707-50-7 C6H7N3S
6-(Tert-butylthio)-7-methoxyimidazo[1,2-a]pyridine 6-(Tert-butylthio)-7-methoxyimidazo[1,2-a]pyridine 2141967-02-2 C12H16N2OS
Disodium (1-methyl-4-oxoimidazolidin-2-ylidene)phosphoramidate Disodium (1-methyl-4-oxoimidazolidin-2-ylidene)phosphoramidate 19604-05-8 C4H9N3NaO4P
2-Ethoxy-3-Bromo-5-Nitropyridine 2-Ethoxy-3-Bromo-5-Nitropyridine 74919-31-6 C7H7BrN2O3
Cyclohexanecarboxamide, N-[2-[(ethylsulfonyl)amino]-5-(trifluoromethyl)-3-pyridinyl]-, sodium salt, hydrate (1:1:1) Cyclohexanecarboxamide, N-[2-[(ethylsulfonyl)amino]-5-(trifluoromethyl)-3-pyridinyl]-, sodium salt, hydrate (1:1:1) 351999-87-6 C15H23F3N3NaO4S
Ethanone, 2,2,2-trifluoro-1-(1-methyl-1H-imidazol-2-yl)- (9CI) Ethanone, 2,2,2-trifluoro-1-(1-methyl-1H-imidazol-2-yl)- (9CI) 62366-56-7 C6H5F3N2O
Pyrrolidine, 2-[(3-bromo-2-thienyl)methyl]- Pyrrolidine, 2-[(3-bromo-2-thienyl)methyl]- 1342415-22-8 C9H12BrNS
4-chloro-2-methylquinazoline 4-chloro-2-methylquinazoline 6484-24-8 C9H7ClN2
2-Pyrimidinamine, 5-(trifluoromethyl)- (9CI) 2-Pyrimidinamine, 5-(trifluoromethyl)- (9CI) 69034-08-8 C5H4F3N3
4H-Pyrazolo[3,4-d]pyrimidin-4-one, 1,5-dihydro-6-methyl- (9CI) 4H-Pyrazolo[3,4-d]pyrimidin-4-one, 1,5-dihydro-6-methyl- (9CI) 30129-57-8 C6H6N4O
8-fluoro-2-methylimidazo[1,2-a]pyridine-6-carbonit 8-fluoro-2-methylimidazo[1,2-a]pyridine-6-carbonit
1-N-TRITYL-IMIDAZOLE-2-YLPROPIONIC ACID
1-N-TRITYL-IMIDAZOLE-2-YLPROPIONIC ACID 675602-85-4 C25H22N2O2
2,4-dichloro-5-ethylpyrimidine 2,4-dichloro-5-ethylpyrimidine C6H6Cl2N2
Methanethione, (4-methoxyphenyl)-1-pyrrolidinyl- Methanethione, (4-methoxyphenyl)-1-pyrrolidinyl- 80282-57-1 C12H15NOS
7-Bromoindole 7-Bromoindole 51417-51-7 C8H6BrN
4-Iodoimidazole 4-Iodoimidazole 71759-89-2 C3H3IN2
INDEX NAME NOT YET ASSIGNED INDEX NAME NOT YET ASSIGNED 1975129-29-3 C18H26BrN6+
1-Ethyl-3,5-dimethyl-1H-pyrazole 1-Ethyl-3,5-dimethyl-1H-pyrazole 17629-26-4 C7H12N2
3-Chloroimidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester 3-Chloroimidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester 1000017-95-7 C10H9ClN2O2
2(3H)-Benzothiazolethione,6-methoxy-(9CI) 2(3H)-Benzothiazolethione,6-methoxy-(9CI) 2182-73-2 C8H7NOS2
2H-Naphth[1,2-d]imidazol-2-one,5-amino-1,3-dihydro-(9CI) 2H-Naphth[1,2-d]imidazol-2-one,5-amino-1,3-dihydro-(9CI) 75370-64-8 C11H9N3O
1H-Pyrazole,5-bromo-1-methyl-(9CI) 1H-Pyrazole,5-bromo-1-methyl-(9CI) 361476-01-9 C4H5BrN2
(S)-3-Fluoro-pyrrolidine hydrochloride (S)-3-Fluoro-pyrrolidine hydrochloride 136725-53-6 C4H9ClFN
2-Aminoimidazole 2-Aminoimidazole 7720-39-0 C3H5N3
5-HYDROXYIMIDACLOPRID 5-HYDROXYIMIDACLOPRID 380912-09-4 C9H10ClN5O3
4-chloro-2-cyclopropylpyrimidine 4-chloro-2-cyclopropylpyrimidine 1044771-74-5 C7H7ClN2
4-CHLOROIMIDAZO/4,5-C/PYRIDINE AND ITS DERIVATIVES 4-CHLOROIMIDAZO/4,5-C/PYRIDINE AND ITS DERIVATIVES
7-BROMO-2,4,9-TRIAZABICYCLO[4.3.0]NONA-3,7,10-TRIEN-5-ONE 7-BROMO-2,4,9-TRIAZABICYCLO[4.3.0]NONA-3,7,10-TRIEN-5-ONE 22276-97-7 C6H4BrN3O
3-BENZYL-3,9-DIAZA-SPIRO[5.5]UNDECANE 3-BENZYL-3,9-DIAZA-SPIRO[5.5]UNDECANE 189333-49-1 C16H24N2
8-Bromo-6-methylimidazo[1,2-a]pyridine-3-carbaldehyde 8-Bromo-6-methylimidazo[1,2-a]pyridine-3-carbaldehyde 1033202-08-2 C9H7BrN2O
5-chloro-2-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine 5-chloro-2-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine 40851-96-5 C7H3ClF3N3
8-BROMO-2-CHLOROQUINAZOLINE 8-BROMO-2-CHLOROQUINAZOLINE 956100-63-3 C8H4BrClN2
ETHYL 6-BROMOIMIDAZO[1,2-A]PYRIMIDINE-2-CARBOXYLIC ACID ETHYL 6-BROMOIMIDAZO[1,2-A]PYRIMIDINE-2-CARBOXYLIC ACID 944896-67-7 C9H8BrN3O2
4-PYRROLIDIN-1-YLMETHYL-PHENYLAMINE 4-PYRROLIDIN-1-YLMETHYL-PHENYLAMINE 142335-64-6 C11H16N2
3,4-Dimethoxy-2-pyridinemethanol 3,4-Dimethoxy-2-pyridinemethanol 72830-08-1 C8H11NO3
6-((Tetrahydro-2H-pyran-2-yl)oxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine 6-((Tetrahydro-2H-pyran-2-yl)oxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine 2135831-65-9 C11H16N2O3
3-Nitro-4-phenylaminopyridine 3-Nitro-4-phenylaminopyridine
9H-Carbazol-9-ol 9H-Carbazol-9-ol 54989-33-2 C12H9NO
4-chloro-6-(trifluoromethyl)quinazoline 4-chloro-6-(trifluoromethyl)quinazoline 16499-64-2 C9H4ClF3N2
1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 5-bromo- 1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 5-bromo- 757978-33-9 C8H5BrN2O
5-Bromobenzo[c][1,2,5]oxadiazole 5-Bromobenzo[c][1,2,5]oxadiazole 51376-06-8 C6H3BrN2O
Carbonylhydrido[6-(di-t-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II), min. 98% Carbonylhydrido[6-(di-t-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II), min. 98% 863971-63-5 C19H35N2PRu.CO
5-IODO-1H-PYRAZOLE 5-IODO-1H-PYRAZOLE 1007351-17-8 C3H3IN2
ETHYL 2-PHENYL-IMIDAZOLE-4-CARBOXYLATE ETHYL 2-PHENYL-IMIDAZOLE-4-CARBOXYLATE 32683-00-4 C12H12N2O2
6-CHLOROBENZIMIDAZOLE-4-CARBOXYLIC ACID 6-CHLOROBENZIMIDAZOLE-4-CARBOXYLIC ACID 180569-27-1 C8H5ClN2O2
5-Trifluoromethoxy-1H-indole 5-Trifluoromethoxy-1H-indole 262593-63-5 C9H6F3NO
5-CHLORO-7-METHOXYTHIENO[3,2-B]PYRIDINE 5-CHLORO-7-METHOXYTHIENO[3,2-B]PYRIDINE 90690-91-8 C8H6ClNOS
1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE-4-BORONIC ACID PINACOL ESTER 1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE-4-BORONIC ACID PINACOL ESTER 454482-11-2 C12H22BNO2
1-(3-BROMOPROPYL)PYRROLIDINE-2,5-DIONE 1-(3-BROMOPROPYL)PYRROLIDINE-2,5-DIONE 88661-56-7 C7H10BrNO2
Ethyl 5-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate Ethyl 5-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate 1260885-46-8 C11H9F3N2O2
4-isocyanato-1-methyl-1H-pyrazole 4-isocyanato-1-methyl-1H-pyrazole 1174064-57-3 C5H5N3O
2-Methoxy-4-(tributylstannyl)pyridine 2-Methoxy-4-(tributylstannyl)pyridine 1204580-72-2 C18H33NOSn
6-Chloropyrimido[5,4-d]pyrimidin-4(3H)-one 6-Chloropyrimido[5,4-d]pyrimidin-4(3H)-one 189747-31-7 C6H3ClN4O
JWH 412 JWH 412 1364933-59-4 C24H22FNO
ethyl 5-amino-1-(pyrimidin-2-yl)-1H-pyrazole-4-carboxylate ethyl 5-amino-1-(pyrimidin-2-yl)-1H-pyrazole-4-carboxylate 91129-95-2 C10H11N5O2
9-Decenoic acid, methyl ester 9-Decenoic acid, methyl ester 25601-41-6 C11H20O2
(S)-3-Methylmorpholine hydrochloride (S)-3-Methylmorpholine hydrochloride 1022094-03-6 C5H12ClNO
4-methoxycarbonyl-6,6'-dimethyl-2,2'-bipyridine 4-methoxycarbonyl-6,6'-dimethyl-2,2'-bipyridine 562086-30-0 C14H14N2O2
7-CHLORO-5-METHYL-1H-PYRAZOLO[4,3-B]PYRIDINE 7-CHLORO-5-METHYL-1H-PYRAZOLO[4,3-B]PYRIDINE 94220-38-9 C7H6ClN3
7-(chloromethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one(SALTDATA: FREE) 7-(chloromethyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one(SALTDATA: FREE) 87572-02-9 C6H4ClN3OS
3-Iodo-2-methoxy-6-(pyrrolidin-1-yl)pyridine 3-Iodo-2-methoxy-6-(pyrrolidin-1-yl)pyridine 1228666-06-5 C10H13IN2O
ethyl 5-oxo-5H-thiazolo[3,2-a]pyriMidine-6-carboxylate ethyl 5-oxo-5H-thiazolo[3,2-a]pyriMidine-6-carboxylate 32278-52-7 C9H8N2O3S
1H-Pyrrolo[2,3-b]pyridine, 5-(4-chlorophenyl)- 1H-Pyrrolo[2,3-b]pyridine, 5-(4-chlorophenyl)- 918516-27-5 C13H9ClN2
N-(2-Methoxyethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine N-(2-Methoxyethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine 1202805-24-0 C13H22BN3O3
1,3-diMethyliMidazoliuM bis((trifluoroMethyl)sulfonyl)iMide 1,3-diMethyliMidazoliuM bis((trifluoroMethyl)sulfonyl)iMide 174899-81-1 C7H9F6N3O4S2
1-propenyl-3-MethyliMidazoliuM nitrate 1-propenyl-3-MethyliMidazoliuM nitrate 649745-76-6 C7H11N3O3
N-Dodecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate N-Dodecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate 14933-08-5 C17H37NO3S
1-tert-butyl-1H-pyrazole-4-carbonitrile 1-tert-butyl-1H-pyrazole-4-carbonitrile 149139-43-5 C8H11N3
tert-Butyl (3S,4R)-4(3-Fluorophenyl)pyrrolidin-3-ylcarbaMate tert-Butyl (3S,4R)-4(3-Fluorophenyl)pyrrolidin-3-ylcarbaMate 1260596-09-5 C15H21FN2O2
N-[3-(1-IMidazolyl)propyl]-2,4-dichlorobenzaMide N-[3-(1-IMidazolyl)propyl]-2,4-dichlorobenzaMide 349092-52-0 C13H13Cl2N3O
IMidazo[1,2-a]pyridine, 8-broMo-6-fluoro- IMidazo[1,2-a]pyridine, 8-broMo-6-fluoro- 1368664-08-7 C7H4BrFN2
IMidazo[1,2-a]pyridine-2-carboxylic acid, 7-Methoxy- IMidazo[1,2-a]pyridine-2-carboxylic acid, 7-Methoxy- 129912-15-8 C9H8N2O3
1H-IMidazole-2-carboxylic acid, 4-[[(1,1-diMethylethoxy)carbonyl]aMino]-1-Methyl-, ethyl ester 1H-IMidazole-2-carboxylic acid, 4-[[(1,1-diMethylethoxy)carbonyl]aMino]-1-Methyl-, ethyl ester 128293-63-0 C12H19N3O4
4-chloro-2-(trifluoroMethyl)-1H-pyrrolo[2,3-b]pyridine 4-chloro-2-(trifluoroMethyl)-1H-pyrrolo[2,3-b]pyridine 1014613-16-1 C8H4ClF3N2
(R)-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole (R)-3-((1-Methylpyrrolidin-2-yl)Methyl)-1H-indole 143322-55-8 C14H18N2
benzyl 2-(5-broMo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate benzyl 2-(5-broMo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate 331842-86-5 C21H19BrN2O3
4-chloro-1-(4-Methoxybenzyl)-1H-iMidazo[4,5-c]pyridine 4-chloro-1-(4-Methoxybenzyl)-1H-iMidazo[4,5-c]pyridine 881844-11-7 C14H12ClN3O
1-(3-Methoxypropyl)-4-oxo-1,4-dihydropyrido[1,2-a]pyrrolo[2,3-d]pyriMidine-2-carboxylic acid 1-(3-Methoxypropyl)-4-oxo-1,4-dihydropyrido[1,2-a]pyrrolo[2,3-d]pyriMidine-2-carboxylic acid 1086386-77-7 C15H15N3O4
IMidazo[1,5-a]pyrazine, 5,6,7,8-tetrahydro-1,3-diMethyl- IMidazo[1,5-a]pyrazine, 5,6,7,8-tetrahydro-1,3-diMethyl- 1083317-78-5 C8H13N3
1H-IMidazole, 4-broMo-1-Methyl-2-(2-Methylphenyl)- 1H-IMidazole, 4-broMo-1-Methyl-2-(2-Methylphenyl)- 1049126-60-4 C11H11BrN2
1,2-Pyrrolidinedicarboxylic acid, 4-(benzoylaMino)-, 1-(1,1-diMethylethyl) 2-Methyl ester, (2S,4R)- 1,2-Pyrrolidinedicarboxylic acid, 4-(benzoylaMino)-, 1-(1,1-diMethylethyl) 2-Methyl ester, (2S,4R)- 943134-37-0 C18H24N2O5
6-broMo-3-chloroiMidazo[1,2-a]pyriMidine 6-broMo-3-chloroiMidazo[1,2-a]pyriMidine 1019025-49-0 C6H3BrClN3
(R)-3-Methylpyrrolidine-3-carboxylic acid (R)-3-Methylpyrrolidine-3-carboxylic acid 1410783-77-5 C6H11NO2
5-AMINO-4-CYANO-3-CYANOMETHYLPYRAZOLE 5-AMINO-4-CYANO-3-CYANOMETHYLPYRAZOLE 54711-21-6 C6H5N5
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