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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-IODO-6-METHYL-IMIDAZO[1,2-A]PYRIDINE 3-IODO-6-METHYL-IMIDAZO[1,2-A]PYRIDINE 885276-23-3 C8H7IN2
5-Methoxyindole 5-Methoxyindole 1006-94-6 C9H9NO
2-(4-CHLORO-PHENYL)-IMIDAZO[1,2-A]PYRIDINE 2-(4-CHLORO-PHENYL)-IMIDAZO[1,2-A]PYRIDINE 38922-74-6 C13H9ClN2
3-BROMO-1-(TRIISOPROPYLSILYL)PYRROLE 3-BROMO-1-(TRIISOPROPYLSILYL)PYRROLE 87630-36-2 C13H24BrNSi
1-[(4-Nitrophenyl)methyl]pyrazole 1-[(4-Nitrophenyl)methyl]pyrazole 110525-57-0 C10H9N3O2
3,5-Diamino-1H-pyrazole 3,5-Diamino-1H-pyrazole 16082-33-0 C3H6N4
5-(CHLOROMETHYL)PYRIDINE-2-CARBALDEHYDE 5-(CHLOROMETHYL)PYRIDINE-2-CARBALDEHYDE 754920-10-0 C7H6ClNO
5-Fluorothiophene-2-carbonitrile 5-Fluorothiophene-2-carbonitrile 32415-91-1 C5H2FNS
2,4-DICHLORO-7-IODO-5H-PYRROLO[3,2-D]PYRIMIDINE 2,4-DICHLORO-7-IODO-5H-PYRROLO[3,2-D]PYRIMIDINE 928840-99-7 C6H2Cl2IN3
3-CHLOROMETHYL-PYRROLIDINE 3-CHLOROMETHYL-PYRROLIDINE 876509-14-7 C5H10ClN
2,6-DICHLORO-N-METHYL-4-PYRIMIDINAMINE 2,6-DICHLORO-N-METHYL-4-PYRIMIDINAMINE 32998-03-1 C5H5Cl2N3
[4-(2-AMINO-ETHYL)-PHENYL]-CARBAMIC ACID TERT-BUTYL ESTER [4-(2-AMINO-ETHYL)-PHENYL]-CARBAMIC ACID TERT-BUTYL ESTER 457631-44-6 C13H20N2O2
N-BOC-3-BROMO-4-HYDROXY-PYRROLIDINE N-BOC-3-BROMO-4-HYDROXY-PYRROLIDINE 1017782-17-0 C9H16BrNO3
6-Amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol 6-Amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol 7400-06-8 C10H17N3O3
1H-pyrazole, 4-iodo-1,3-dimethyl- 1H-pyrazole, 4-iodo-1,3-dimethyl- 6647-97-8 C5H7IN2
3-(1H-Benzimidazol-1-yl)propanenitrile 3-(1H-Benzimidazol-1-yl)propanenitrile 4414-84-0 C10H9N3
1-hydroxybenzotriazole monohydrate 1-hydroxybenzotriazole monohydrate C6H7N3O2
2-Bromo-5-fluoropyridine 1-oxide 2-Bromo-5-fluoropyridine 1-oxide 935534-39-7 C5H3BrFNO
3-[(2S)-1,2,3,6-tetrahydropyridin-2-yl]pyridine 3-[(2S)-1,2,3,6-tetrahydropyridin-2-yl]pyridine 581-49-7 C10H12N2
SMMC7721/FU SMMC7721/FU
3-amino-5-methyl-1H-pyrazole-4-carbonitrile 3-amino-5-methyl-1H-pyrazole-4-carbonitrile 5453-07-6 C5H6N4
(3R,4R)-N-Cbz-3,4-difluoropyrrolidine (3R,4R)-N-Cbz-3,4-difluoropyrrolidine 790658-58-1 C12H13F2NO2
1H-1,2,4-Triazole,1-phenyl-(6CI,7CI,8CI,9CI) 1H-1,2,4-Triazole,1-phenyl-(6CI,7CI,8CI,9CI) 13423-60-4 C8H7N3
1H-Benzimidazole-2-carboxylicacid,5-methyl-(9CI) 1H-Benzimidazole-2-carboxylicacid,5-methyl-(9CI) 99459-47-9 C9H8N2O2
1H-Benzimidazole,2-cyclopropyl-(9CI) 1H-Benzimidazole,2-cyclopropyl-(9CI) 16405-79-1 C10H10N2
1H-Benzimidazol-5-ol,2-amino-(9CI) 1H-Benzimidazol-5-ol,2-amino-(9CI) 51276-85-8 C7H7N3O
2-Butanone,4-(1H-benzimidazol-2-yl)-(9CI) 2-Butanone,4-(1H-benzimidazol-2-yl)-(9CI) 19276-01-8 C11H12N2O
(4-Pyrazol-1-ylphenyl)methanol (4-Pyrazol-1-ylphenyl)methanol 143426-49-7 C10H10N2O
2-(Hydroxymethyl)pyrrolidine 2-(Hydroxymethyl)pyrrolidine 498-63-5 C5H11NO
1-Benzyl-1H-pyrazol-4-amine 1-Benzyl-1H-pyrazol-4-amine 28466-62-8 C10H11N3
2-Phenyl-1H-benzo[d]imidazol-5-amine 2-Phenyl-1H-benzo[d]imidazol-5-amine 1767-25-5 C13H11N3
4-(4-CHLORO-6-METHYL-2-PYRIMIDINYL)MORPHOLINE 4-(4-CHLORO-6-METHYL-2-PYRIMIDINYL)MORPHOLINE 118121-82-7 C9H12ClN3O
ethyl4-chlorothieno[3,2-d]pyrimidine-6-carboxylate ethyl4-chlorothieno[3,2-d]pyrimidine-6-carboxylate 596794-87-5 C9H7ClN2O2S
5-AMINO-1-METHYLIMIDAZOLE 5-AMINO-1-METHYLIMIDAZOLE 66787-75-5 C4H7N3
Ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)-4-hydroxypyrimidine-5-carboxylate Ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)-4-hydroxypyrimidine-5-carboxylate 1065074-31-8 C16H24N4O5
6-Bromo-2-chloroquinazoline 6-Bromo-2-chloroquinazoline 882672-05-1 C8H4BrClN2
ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate 860457-99-4 C11H9F3N2O2
Nornicotine-2-carboxylic Acid Nornicotine-2-carboxylic Acid 3562-11-6 C10H12N2O2
4-BROMO-3,5-DIMETHYL-1-(TETRAHYDRO-2H-PYRAN-4-YL)-1H-PYRAZOLE 4-BROMO-3,5-DIMETHYL-1-(TETRAHYDRO-2H-PYRAN-4-YL)-1H-PYRAZOLE 1339665-24-5 C10H15BrN2O
2,4-DIAMINO-1,3,5-TRIAZINE 2,4-DIAMINO-1,3,5-TRIAZINE 504-08-5 C3H5N5
2-NONYLBENZIMIDAZOLE 2-NONYLBENZIMIDAZOLE 5851-50-3 C16H24N2
1,5-Dimethylpyrazole 1,5-Dimethylpyrazole 694-31-5 C5H8N2
(S)-4-(4-CHLOROPHENYL)PYRROLIDIN-2-ONE (S)-4-(4-CHLOROPHENYL)PYRROLIDIN-2-ONE 123632-31-5 C10H10ClNO
5-BROMO-2,3-DIHYDROSPIRO[IMIDAZOLIDINE-4,1-INDENE]-2,5-DIONE 5-BROMO-2,3-DIHYDROSPIRO[IMIDAZOLIDINE-4,1-INDENE]-2,5-DIONE 553680-99-2 C11H9BrN2O2
4-Bromo-3,5-dimethylpyrazole 4-Bromo-3,5-dimethylpyrazole 3398-16-1 C5H7BrN2
4-Bromo-1H-indazole 4-Bromo-1H-indazole 186407-74-9 C7H5BrN2
2,3-Dihydrofuran 2,3-Dihydrofuran 1191-99-7 C4H6O
4-(1H-IMIDAZOL-4-YLMETHYL)PIPERIDINE DIHYDROBROMIDE 4-(1H-IMIDAZOL-4-YLMETHYL)PIPERIDINE DIHYDROBROMIDE 164391-47-3 C9H17Br2N3
(3R,4R)-(-)-1-BENZYL-3,4-PYRROLIDINDIOL (3R,4R)-(-)-1-BENZYL-3,4-PYRROLIDINDIOL 76784-33-3 C11H15NO2
2,3,6-Trimethylimidazo[2,1-b]thiazole-5-carboxylic acid 2,3,6-Trimethylimidazo[2,1-b]thiazole-5-carboxylic acid 1007875-80-0 C9H10N2O2S
4-Aminothieno[2,3-d]pyrimidine-6-carbaldehyde 4-Aminothieno[2,3-d]pyrimidine-6-carbaldehyde 655254-90-3 C7H5N3OS
6'-Bromo-8'-methyl-1'H-spiro[cyclopentane-1,3'-imidazo[1,5-a]pyridine]-1',5'(2'H)-dione 6'-Bromo-8'-methyl-1'H-spiro[cyclopentane-1,3'-imidazo[1,5-a]pyridine]-1',5'(2'H)-dione 1849592-55-7 C12H13BrN2O2
2,3-BENZOCARBAZOLE 2,3-BENZOCARBAZOLE 243-28-7 C16H11N
{5H,6H,7H,8H-imidazo[1,2-a]pyridin-2-ylmethyl}(methyl)amine {5H,6H,7H,8H-imidazo[1,2-a]pyridin-2-ylmethyl}(methyl)amine 1500012-34-9 C9H15N3
2-(1H-Pyrazol-1-yl)pyrimidine-5-boronic acid pinacol ester 2-(1H-Pyrazol-1-yl)pyrimidine-5-boronic acid pinacol ester 1449009-97-5 C13H17BN4O2
6-(Ethyl(phenyl)amino)-2-methylpyrimidin-4(3H)-one 6-(Ethyl(phenyl)amino)-2-methylpyrimidin-4(3H)-one 133062-55-2 C13H15N3O
2'-(Methylsulfonyl)-7',8'-dihydro-6'H-spiro[cyclohexane-1,9'-pyrazino[1',2':1,5]pyrrolo[2,3-d]pyrimidin]-6'-one 2'-(Methylsulfonyl)-7',8'-dihydro-6'H-spiro[cyclohexane-1,9'-pyrazino[1',2':1,5]pyrrolo[2,3-d]pyrimidin]-6'-one 2170747-01-8 C15H18N4O3S
(2R,4S)-4-fluoro-2-methylpyrrolidine (2R,4S)-4-fluoro-2-methylpyrrolidine 1670259-96-7 C5H10FN
5-aminothiazolo[4,5-d]pyrimidine-2(3H)-thione 5-aminothiazolo[4,5-d]pyrimidine-2(3H)-thione 892498-86-1 C5H4N4S2
Bis-(4-tert-butylphenyl)-iodonium bis(trifluoromethylsulfonyl)imide Bis-(4-tert-butylphenyl)-iodonium bis(trifluoromethylsulfonyl)imide 460731-32-2
3-METHYL-2-BENZOTHIAZOLINONE HYDRAZONE HYDROCHLORIDE 3-METHYL-2-BENZOTHIAZOLINONE HYDRAZONE HYDROCHLORIDE 14448-67-0 C8H10ClN3S
(S)-(+)-N-BOC-3-N-FMOC-AMINOPYRROLIDINE& (S)-(+)-N-BOC-3-N-FMOC-AMINOPYRROLIDINE& 307531-88-0 C24H28N2O4
5-Ethynyl-1-methyl-1H-imidazole 5-Ethynyl-1-methyl-1H-imidazole 71759-92-7 C6H6N2
(R)-1-FMOC-3-Pyrrolidinol (R)-1-FMOC-3-Pyrrolidinol 215178-39-5 C19H19NO3
TubePharm10tm TubePharm10tm 1589503-96-7 C27H22F2N6O5S
1,4-bis(2-methyl-1H-imidazol-1-yl)benzene 1,4-bis(2-methyl-1H-imidazol-1-yl)benzene 1347702-71-9 C14H14N4
Benzyl 2,4-dichloro-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate Benzyl 2,4-dichloro-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate 1990514-48-1 C14H11Cl2N3O2
4-[chloromethyl(morpholin-4-yl)phosphoryl]morpholine 4-[chloromethyl(morpholin-4-yl)phosphoryl]morpholine 7355-28-4 C9H18ClN2O3P
Manufacturer of phenacetin API Manufacturer of phenacetin API
1‘-benzyl-7H-spiro[furo[3,4-b]pyridine-5,4’-piperidin]-7-one 1‘-benzyl-7H-spiro[furo[3,4-b]pyridine-5,4’-piperidin]-7-one 1036408-83-9 C18H18N2O2
N,N-Dimethyl-1H-pyrazole-3-carboxamide N,N-Dimethyl-1H-pyrazole-3-carboxamide 853058-59-0 C6H9N3O
(S)-2-(3-Fluoropyrrolidin-1-yl)ethan-1-ol (S)-2-(3-Fluoropyrrolidin-1-yl)ethan-1-ol 1240710-87-5 C6H12FNO
2-(6-Methoxyimidazo[1,2-a]pyridin-3-yl)acetamide 2-(6-Methoxyimidazo[1,2-a]pyridin-3-yl)acetamide 603309-64-4 C10H11N3O2
3-METHYL-PYRROLIDINE-3-CARBOXYLIC ACID 3-METHYL-PYRROLIDINE-3-CARBOXYLIC ACID 885953-27-5 C6H11NO2
3-IODO-1-METHYL-1H-PYRAZOLE 3-IODO-1-METHYL-1H-PYRAZOLE 92525-10-5 C4H5IN2
N-METHANESULFONYLIMIDAZOLE N-METHANESULFONYLIMIDAZOLE 40736-26-3 C4H6N2O2S
5-Chloro-2-phenyl-3H-imidazole-4-carbaldehyde 5-Chloro-2-phenyl-3H-imidazole-4-carbaldehyde 60367-52-4 C10H7ClN2O
5-NITROOROTIC ACID 5-NITROOROTIC ACID 17687-24-0 C5H3N3O6
5,5'-(pyrimidine-2,5-diyl)diisophthalic acid 5,5'-(pyrimidine-2,5-diyl)diisophthalic acid 1601485-40-8 C20H12N2O8
1-BUTYL-3-METHYLIMIDAZOLIUM (L)-LACTATE 1-BUTYL-3-METHYLIMIDAZOLIUM (L)-LACTATE 878132-20-8 C11H20N2O3
3-METHYL-5-(TRIFLUOROMETHYL)PYRAZOLE 3-METHYL-5-(TRIFLUOROMETHYL)PYRAZOLE 10010-93-2 C5H5F3N2
8-NITRO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER 8-NITRO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER 72721-23-4 C10H9N3O4
(S)-3-AMINO-1-CBZ-PYRROLIDINE (S)-3-AMINO-1-CBZ-PYRROLIDINE 122536-72-5 C12H16N2O2
6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE 6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE 1745-07-9 C11H15NO2
4-IMIDAZO[1,2-A]PYRIDIN-2-YLPHENYL METHYL ETHER 4-IMIDAZO[1,2-A]PYRIDIN-2-YLPHENYL METHYL ETHER 31562-99-9 C14H12N2O
6-METHYL-2-PHENYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE 6-METHYL-2-PHENYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE 727975-78-2 C15H12N2O
4-PYRAZOL-1-YL-BENZONITRILE 4-PYRAZOL-1-YL-BENZONITRILE 25699-83-6 C10H7N3
2,6-Bis((bis(2-methylphenyl)phosphino))methyl)pyridine 2,6-Bis((bis(2-methylphenyl)phosphino))methyl)pyridine 501663-96-3 C35H35NP2
N,N'-(butane-1,4-diyl)bis(1-(benzyloxy)-N-(3-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)propyl)-6-oxo-1,6-dihydropyridine-2-carboxamide) N,N'-(butane-1,4-diyl)bis(1-(benzyloxy)-N-(3-(1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxamido)propyl)-6-oxo-1,6-dihydropyridine-2-carboxamide) C62H62N8O12
3,3'-dimethyl-1H,1H'-4,4'-bipyrazole 3,3'-dimethyl-1H,1H'-4,4'-bipyrazole 1816270-47-9 C8H10N4
4-Pyridinecarboxamide, 2-chloro-3-methoxy- 4-Pyridinecarboxamide, 2-chloro-3-methoxy- 1935682-11-3 C7H7ClN2O2
6-FLUORO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 6-FLUORO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 367900-94-5 C8H5FN2O2
Butonitazene Butonitazene 95810-54-1 C24H32N4O3
(S)-ALPHA,ALPHA-BIS(4-FLUOROPHENYL)-2-PYRROLIDINEMETHANOL (S)-ALPHA,ALPHA-BIS(4-FLUOROPHENYL)-2-PYRROLIDINEMETHANOL 131180-45-5 C17H17F2NO
1,2,4-Triazine-3,5(2H,4H)-dione, 6-(3-amino-1-pyrrolidinyl)- 1,2,4-Triazine-3,5(2H,4H)-dione, 6-(3-amino-1-pyrrolidinyl)- 1249530-93-5 C7H11N5O2
Pyrimidine, 4-hydrazinyl-2-(2-pyridinyl)-6-(trifluoromethyl)- Pyrimidine, 4-hydrazinyl-2-(2-pyridinyl)-6-(trifluoromethyl)- 1306604-16-9 C10H8F3N5
2-Pyrrolidinecarboximidamide 2-Pyrrolidinecarboximidamide 1310457-96-5 C5H11N3
3-(4-METHOXYPHENYL)PYRROLIDINE 3-(4-METHOXYPHENYL)PYRROLIDINE 91246-26-3 C11H15NO
4-(4-BROMO-PHENYL)-1H-IMIDAZOLE 4-(4-BROMO-PHENYL)-1H-IMIDAZOLE 13569-96-5 C9H7BrN2
4-BROMO-3-PHENYL-1H-PYRAZOLE 4-BROMO-3-PHENYL-1H-PYRAZOLE 13808-65-6 C9H7BrN2
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