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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
5-Bromo-4-ethyl-2-(n-propyl)thiazole 5-Bromo-4-ethyl-2-(n-propyl)thiazole 1643543-28-5 C8H12BrNS
5-bromo-4-fluoro-2-(methyl-d3)pyridine-3,6-d2 5-bromo-4-fluoro-2-(methyl-d3)pyridine-3,6-d2 2294944-83-3 C6H5BrFN
5-Bromo-4-hydroxy-2-(n-propyl)pyrimidine 5-Bromo-4-hydroxy-2-(n-propyl)pyrimidine 1515840-17-1 C7H9BrN2O
5-bromopyrimidine-2,4-d2 5-bromopyrimidine-2,4-d2 2222933-93-7 C4H3BrN2
5-Hydroxy-2-(3-trifluoromethylphenyl)thiazole 5-Hydroxy-2-(3-trifluoromethylphenyl)thiazole 1159814-53-5 C10H6F3NOS
5-methyl-1H-1,2,3-triazol-4-amine 5-methyl-1H-1,2,3-triazol-4-amine 60419-73-0 C3H6N4
6-(3-BROMOPHENYL)PYRIDIN-2-AMINE 6-(3-BROMOPHENYL)PYRIDIN-2-AMINE 1368036-48-9 C11H9BrN2
6-(methoxy-d3)pyridazin-4,5-d2-3-amine 6-(methoxy-d3)pyridazin-4,5-d2-3-amine 2256707-48-7 C5H7N3O
6-(methoxy-d3)pyrimidin-2,5-d2-4-amine 6-(methoxy-d3)pyrimidin-2,5-d2-4-amine 2256707-50-1 C5H7N3O
6-(tetrahydrofuran-3-yl)pyrimidin-4-ol 6-(tetrahydrofuran-3-yl)pyrimidin-4-ol 2222935-32-0 C8H10N2O2
6-bromopyrimidin-2,5-d2-4-amine 6-bromopyrimidin-2,5-d2-4-amine 2241865-59-6 C4H2BrD2N3
Methyl 4-Bromo-2-methylpyridine-3-carboxylate Methyl 4-Bromo-2-methylpyridine-3-carboxylate 1374664-86-4 C8H8BrNO2
N-Boc-2-Bromomorpholine N-Boc-2-Bromomorpholine 1622834-75-6 C9H16BrNO3
tert-butyl 3-(2-aminopyrimidin-4-yl)pyrrolidine-1-carboxylate tert-butyl 3-(2-aminopyrimidin-4-yl)pyrrolidine-1-carboxylate 1823811-53-5 C13H20N4O2
TERT-BUTYL 4-(3-AMINOPYRIDIN-2-YL)PIPERIDINE-1-CARBOXYLATE TERT-BUTYL 4-(3-AMINOPYRIDIN-2-YL)PIPERIDINE-1-CARBOXYLATE 873000-10-3 C15H23N3O2
TERT-BUTYL 4-(4-AMINOPYRIDIN-3-YL)PIPERIDINE-1-CARBOXYLATE TERT-BUTYL 4-(4-AMINOPYRIDIN-3-YL)PIPERIDINE-1-CARBOXYLATE 1245915-83-6 C15H23N3O2
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
tert-butyl 7,7-difluoro-3,9-diazaspiro[5.5]undecane-3-carboxylate tert-butyl 7,7-difluoro-3,9-diazaspiro[5.5]undecane-3-carboxylate 1784848-04-9 C14H24F2N2O2
1-isopropyl-3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 1-isopropyl-3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 2068065-34-7 C13H23BN2O2
5-aminothiazolo[4,5-d]pyrimidine-2(3H)-thione 5-aminothiazolo[4,5-d]pyrimidine-2(3H)-thione 892498-86-1 C5H4N4S2
5-Bromo-2-isopropoxy-4-methylpyrimidine 5-Bromo-2-isopropoxy-4-methylpyrimidine 1896867-78-9 C8H11BrN2O
Bis-(4-tert-butylphenyl)-iodonium bis(trifluoromethylsulfonyl)imide Bis-(4-tert-butylphenyl)-iodonium bis(trifluoromethylsulfonyl)imide 460731-32-2
N-[6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-L-alanine N-[6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-L-alanine 1342211-31-7 C18H27N3O6
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
2-Amino-6-(pyrrolidin-2-yl)pyridine 2-Amino-6-(pyrrolidin-2-yl)pyridine 1270472-98-4 C9H13N3
2-(3-Tetrahydrofuranyl)aniline 2-(3-Tetrahydrofuranyl)aniline 1353854-21-3 C10H13NO
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
1-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydropyridine 1-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydropyridine C12H22BNO2
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
Oxazole, 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]- Oxazole, 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]- 1603136-79-3 C15H18BNO3
4-[chloromethyl(morpholin-4-yl)phosphoryl]morpholine 4-[chloromethyl(morpholin-4-yl)phosphoryl]morpholine 7355-28-4 C9H18ClN2O3P
[2,2'-Bipyridine]-5-methanamine, 6'-bromo- [2,2'-Bipyridine]-5-methanamine, 6'-bromo- 334001-83-1 C11H10BrN3
'2-chloro-5-fluoropyridine-3,4,6-d3 '2-chloro-5-fluoropyridine-3,4,6-d3 2363786-75-6 C5H3ClFN
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
3-bromo-1-(propan-2-yl)-1H-1,2,4-triazole 3-bromo-1-(propan-2-yl)-1H-1,2,4-triazole 1823441-99-1 C5H8BrN3
Pyridine, 4-methyl-2-(1-methylethyl)- Pyridine, 4-methyl-2-(1-methylethyl)- 4855-56-5 C9H13N
Pyridine, 5-bromo-2-(2-oxazolyl)- Pyridine, 5-bromo-2-(2-oxazolyl)- 1201643-61-9 C8H5BrN2O
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
1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE 1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE 66121-69-5 C5H5N3
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
Imidazo[1,5-a]pyridine, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Imidazo[1,5-a]pyridine, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2710294-48-5 C13H17BN2O2
3,5-DIMETHYL-4H-1,2,4-TRIAZOLE 3,5-DIMETHYL-4H-1,2,4-TRIAZOLE 7343-34-2 C4H7N3
Propanoic acid, 2,2-dimethyl-, [2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl]methyl ester Propanoic acid, 2,2-dimethyl-, [2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl]methyl ester 2241865-17-6 C15H27BO4
Dimiracetam Dimiracetam 126100-97-8 C6H8N2O2
1H-1,2,3-Triazole, 5-[2-(trifluoromethyl)phenyl]- 1H-1,2,3-Triazole, 5-[2-(trifluoromethyl)phenyl]- 872701-01-4 C9H6F3N3
Pyridine, 3-bromo-5-(3-oxetanyloxy)- Pyridine, 3-bromo-5-(3-oxetanyloxy)- 1592388-39-0 C8H8BrNO2
(5-fluoropyridin-3-yl-2,4,6-d3)boronic acid (5-fluoropyridin-3-yl-2,4,6-d3)boronic acid 2819702-17-3 C5H5BFNO2
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
3-BROMO-2-IMIDAZOL-1-YL-PYRIDINE 3-BROMO-2-IMIDAZOL-1-YL-PYRIDINE 190198-42-6 C8H6BrN3
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-CHLORO-6-ETHYL-PYRIDAZINE 3-CHLORO-6-ETHYL-PYRIDAZINE 98198-61-9 C6H7ClN2
2-BROMO-4-(3,5-DIFLUORO-PHENYL)-THIAZOLE 2-BROMO-4-(3,5-DIFLUORO-PHENYL)-THIAZOLE 886367-95-9 C9H4BrF2NS
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
[2,2'-Bipyridine]-5-carbonitrile, 4'-chloro- [2,2'-Bipyridine]-5-carbonitrile, 4'-chloro- 1185306-12-0 C11H6ClN3
1H-Pyrazole, 1-(tetrahydro-2H-pyran-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1H-Pyrazole, 1-(tetrahydro-2H-pyran-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2223009-52-5 C14H23BN2O3
Thiazole, 5-bromo-4-(2-furanyl)- Thiazole, 5-bromo-4-(2-furanyl)- 1374665-36-7 C7H4BrNOS
6-FLUORO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 6-FLUORO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 367900-94-5 C8H5FN2O2
1,3,5-Triazin-2(1H)-one, 6-methyl- 1,3,5-Triazin-2(1H)-one, 6-methyl- 1643538-43-5 C4H5N3O
1H-Pyrazole, 4-(2-bromophenyl)- 1H-Pyrazole, 4-(2-bromophenyl)- 1260795-26-3 C9H7BrN2
Butonitazene Butonitazene 95810-54-1 C24H32N4O3
1H-1,2,3-Triazole, 5-cyclohexyl- 1H-1,2,3-Triazole, 5-cyclohexyl- 1044856-72-5 C8H13N3
(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
1H-1,2,3-Triazole, 5-bromo-1-cyclopropyl- 1H-1,2,3-Triazole, 5-bromo-1-cyclopropyl- 1889670-37-4 C5H6BrN3
2-Pyrrolidinecarboximidamide 2-Pyrrolidinecarboximidamide 1310457-96-5 C5H11N3
Pyridine, 4-bromo-2-(1H-imidazol-2-yl)- Pyridine, 4-bromo-2-(1H-imidazol-2-yl)- 1211579-82-6 C8H6BrN3
1H-1,2,3-Triazole, 1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1H-1,2,3-Triazole, 1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2222997-19-3 C13H22BN3O3
3-(4-METHOXYPHENYL)PYRROLIDINE 3-(4-METHOXYPHENYL)PYRROLIDINE 91246-26-3 C11H15NO
2-Pyridinamine, 4-cyclopropyl-6-methyl- 2-Pyridinamine, 4-cyclopropyl-6-methyl- 1314968-28-9 C9H12N2
2-Pyridinecarbonitrile, 4-bromo-6-fluoro- 2-Pyridinecarbonitrile, 4-bromo-6-fluoro- 1804381-07-4 C6H2BrFN2
Pyridine, 6-bromo-3-methyl-2-(trifluoromethyl)- Pyridine, 6-bromo-3-methyl-2-(trifluoromethyl)- 1211538-39-4 C7H5BrF3N
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
1-[(DIMETHYLAMINO)METHYL]IMIDAZOLE 1-[(DIMETHYLAMINO)METHYL]IMIDAZOLE 23230-39-9 C6H11N3
Thiazole, 2-(4-ethylphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Thiazole, 2-(4-ethylphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1402227-39-7 C17H22BNO2S
3-(3-Bromophenyl)-1-methyl-1H-pyrazole 3-(3-Bromophenyl)-1-methyl-1H-pyrazole 425379-68-6 C10H9BrN2
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