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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
2,4-DIHYDROXY-6-NITROQUINAZOLINE 2,4-DIHYDROXY-6-NITROQUINAZOLINE 32618-85-2 C8H5N3O4
3-Piperidinone 3-Piperidinone 50717-82-3 C5H9NO
(S)-1-N-Boc-2-methylpiperazine (S)-1-N-Boc-2-methylpiperazine 169447-70-5 C10H20N2O2
3,5-DIMETHYL-1-PHENYLPYRAZOLE 3,5-DIMETHYL-1-PHENYLPYRAZOLE 1131-16-4 C11H12N2
1-[[2,4,6-Tris(isopropyl)phenyl]sulphonyl]-1H-1,2,4-triazole 1-[[2,4,6-Tris(isopropyl)phenyl]sulphonyl]-1H-1,2,4-triazole 54230-60-3 C17H25N3O2S
4-ACETYL-5-METHYL-1-PHENYLPYRAZOLE 4-ACETYL-5-METHYL-1-PHENYLPYRAZOLE 6123-63-3 C12H12N2O
(3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE (3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE 131878-23-4 C16H24N2O2
(R)-3-AMINOMETHYL-1-CBZ-PYRROLIDINE (R)-3-AMINOMETHYL-1-CBZ-PYRROLIDINE 1217749-69-3 C13H18N2O2
5-(3-BROMO-PHENYL)-1H-PYRAZOLE 5-(3-BROMO-PHENYL)-1H-PYRAZOLE 149739-65-1 C9H7BrN2
5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE 5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE 5334-43-0 C10H8N4
2-(4-BROMO-1H-IMIDAZOL-2-YL)-PYRIDINE 2-(4-BROMO-1H-IMIDAZOL-2-YL)-PYRIDINE 71048-48-1 C8H6BrN3
[2,2'-Bipyridin]-5-ol, 6'-bromo- [2,2'-Bipyridin]-5-ol, 6'-bromo- 1185307-68-9 C10H7BrN2O
3-(4-Bromo-3-methyl-2-oxo-2,3-dihydro-1h-benzo[d]imidazol-1-yl)piperidine-2,6-dione 3-(4-Bromo-3-methyl-2-oxo-2,3-dihydro-1h-benzo[d]imidazol-1-yl)piperidine-2,6-dione 2304754-51-4 C13H12BrN3O3
2,2'-(cyclopropane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 2,2'-(cyclopropane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 2222867-16-3 C15H28B2O4
1-(oxan-4-yl)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 1-(oxan-4-yl)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 2223054-66-6 C14H23BN2O3
2,2'-Bioxazole, 4,4',5,5'-tetrahydro-4,4'-bis[(1S)-1-methylpropyl]-, (4S,4'S)- 2,2'-Bioxazole, 4,4',5,5'-tetrahydro-4,4'-bis[(1S)-1-methylpropyl]-, (4S,4'S)- 133463-89-5 C14H24N2O2
4(1H)-Pyrimidinone, 2,5,6-trichloro- 4(1H)-Pyrimidinone, 2,5,6-trichloro- 24688-43-5 C4HCl3N2O
1,4-bis(1-(4-methyl)imidazolyl)benzene 1,4-bis(1-(4-methyl)imidazolyl)benzene 1627843-75-7 C14H14N4
4-(1H-IMIDAZOL-2-YL)-PYRIDINE 4-(1H-IMIDAZOL-2-YL)-PYRIDINE 21202-42-6 C8H7N3
1H-1,2,3-Triazole, 5-(3-methoxyphenyl)- 1H-1,2,3-Triazole, 5-(3-methoxyphenyl)- 1017579-86-0 C9H9N3O
Thiazole, 4-bromo-5-ethyl- Thiazole, 4-bromo-5-ethyl- 1264033-99-9 C5H6BrNS
Boronic acid, B-[4-(2-pyrimidinyl)phenyl]- Boronic acid, B-[4-(2-pyrimidinyl)phenyl]- 1615248-01-5 C10H9BN2O2
Boronic acid, B-[4-(4-pyrimidinyl)phenyl]- Boronic acid, B-[4-(4-pyrimidinyl)phenyl]- 1907696-52-9 C10H9BN2O2
4-Pyrimidinamine, 5-bromo-2-(1-methylethyl)- 4-Pyrimidinamine, 5-bromo-2-(1-methylethyl)- 1381942-46-6 C7H10BrN3
5-AMINO-3-METHYL-PYRIDIN-2-OL 5-AMINO-3-METHYL-PYRIDIN-2-OL 20252-07-7 C6H8N2O
2H-Tetrazole, 5-bromo-2-(1-methylethyl)- 2H-Tetrazole, 5-bromo-2-(1-methylethyl)- 1783421-43-1 C4H7BrN4
7-BROMO-4-CHLOROQUINAZOLINE 7-BROMO-4-CHLOROQUINAZOLINE 573675-55-5 C8H4BrClN2
7-Bromoquinazoline 7-Bromoquinazoline 89892-22-8 C8H5BrN2
Acridine Acridine 260-94-6 C13H9N
2-Octylbenzimidazole 2-Octylbenzimidazole 13060-24-7 C15H22N2
Morpholine, 4-(4-bromo-3-methoxyphenyl)- Morpholine, 4-(4-bromo-3-methoxyphenyl)- 221360-89-0 C11H14BrNO2
Pyridine, 2-bromo-5-(1H-imidazol-2-yl)- Pyridine, 2-bromo-5-(1H-imidazol-2-yl)- 1211583-15-1 C8H6BrN3
1,3,2-Dioxaborolane, 2-(3-bromo-2-furanyl)-4,4,5,5-tetramethyl- 1,3,2-Dioxaborolane, 2-(3-bromo-2-furanyl)-4,4,5,5-tetramethyl- 1802557-95-4 C10H14BBrO3
2-Thiazolamine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-2-thiazolyl- 2-Thiazolamine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-2-thiazolyl- 1402174-68-8 C12H16BN3O2S2
ARV110 ARV110 2222112-77-6 C41H43ClFN9O6
Fasoracetam Fasoracetam 110958-19-5 C10H16N2O2
(S)-2-(4-Fluorophenyl)pyrrolidine (S)-2-(4-Fluorophenyl)pyrrolidine 298690-90-1 C10H12FN
Pyridine, 3-(2-methoxyethoxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Pyridine, 3-(2-methoxyethoxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1628707-47-0 C14H22BNO4
6-phenyluracil 6-phenyluracil 13345-09-0 C10H8N2O2
1-(3-Chlorophenyl)imidazolidin-2-one 1-(3-Chlorophenyl)imidazolidin-2-one 14088-98-3 C9H9ClN2O
N-[2-(4-Oxo-4H-3,1-benzoxazin-2-yl)phenyl]-2-naphthalenesulfonamide N-[2-(4-Oxo-4H-3,1-benzoxazin-2-yl)phenyl]-2-naphthalenesulfonamide 10128-55-9 C24H16N2O4S
1H-Pyrazole, 3,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1H-Pyrazole, 3,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2368225-26-5 C11H19BN2O2
2-(3-pentenyl)pyridine 2-(3-pentenyl)pyridine 2057-43-4 C10H13N
(S)-2-Tert-butoxycarbonylamino-3-quinolin-6-yl-propionic acid (S)-2-Tert-butoxycarbonylamino-3-quinolin-6-yl-propionic acid 162677-20-5 C17H20N2O4
1-ethyl-4-(2-morpholinoethyl)-3,3-diphenylpyrrolidin-2-one monohydrochloride 1-ethyl-4-(2-morpholinoethyl)-3,3-diphenylpyrrolidin-2-one monohydrochloride 113-07-5 C24H31ClN2O2
5-BROMO-2-ISOPROPYLOXAZOLE 5-BROMO-2-ISOPROPYLOXAZOLE 1391739-84-6 C6H8BrNO
6-Bromo-2-(5''-cyano-2''-pyridyl)pyrazine 6-Bromo-2-(5''-cyano-2''-pyridyl)pyrazine 1185318-78-8 C10H5BrN4
1H-Pyrrolizine-7a(5H)-methanol, 2,6-difluorotetrahydro- 1H-Pyrrolizine-7a(5H)-methanol, 2,6-difluorotetrahydro- 2621938-62-1 C8H13F2NO
(S)-2-methyl-6-(pyrrolidin-2-yl)pyridine (S)-2-methyl-6-(pyrrolidin-2-yl)pyridine 1213442-21-7 C10H14N2
Hexamethylol melamine Hexamethylol melamine 531-18-0 C9H18N6O6
2-Pyridinamine, 4-(1,1-dimethylethyl)-6-methyl- 2-Pyridinamine, 4-(1,1-dimethylethyl)-6-methyl- 908271-20-5 C10H16N2
3,4,5-Trimethyl-1H-pyrazole 3,4,5-Trimethyl-1H-pyrazole 5519-42-6 C6H10N2
N-METHYLFULLEROPYRROLIDINE N-METHYLFULLEROPYRROLIDINE 151872-44-5 C63H7N
(2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95% (2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95% 415678-40-9 C16H18N2O2
4-Ethyl-1,3,5-triazin-2-amine 4-Ethyl-1,3,5-triazin-2-amine 30360-34-0 C5H8N4
4-Fluoro-2-(2-aminophenyl)pyridine 4-Fluoro-2-(2-aminophenyl)pyridine 1563530-76-6 C11H9FN2
4-Fluoro-2-(3-bromophenyl)pyridine 4-Fluoro-2-(3-bromophenyl)pyridine 1563529-99-6 C11H7BrFN
4-Fluoro-2-(3-methoxyphenyl)pyridine 4-Fluoro-2-(3-methoxyphenyl)pyridine 1497434-84-0 C12H10FNO
4-Fluoro-2-(4-methyl-1H-pyrazol-1-yl)pyridine-5-boronic acid pinacol ester 4-Fluoro-2-(4-methyl-1H-pyrazol-1-yl)pyridine-5-boronic acid pinacol ester 2223033-93-8 C15H19BFN3O2
4-Fluoro-2-(4-tolyl)pyridine 4-Fluoro-2-(4-tolyl)pyridine 1563529-60-1 C12H10FN
4-Fluoro-2-(n-propyl)pyridine 4-Fluoro-2-(n-propyl)pyridine 1563531-51-0 C8H10FN
4-Fluoro-2-(tert-butoxy)pyridine-5-boronic acid pinacol ester 4-Fluoro-2-(tert-butoxy)pyridine-5-boronic acid pinacol ester 2223045-25-6 C15H23BFNO3
4-Hydroxy-2-(cyclobutyl)pyrimidine 4-Hydroxy-2-(cyclobutyl)pyrimidine 1159816-67-7 C8H10N2O
4-Hydroxy-2-(iso-propyl)-6-(1H-4-methylimidazol-1-yl)-pyrimidine 4-Hydroxy-2-(iso-propyl)-6-(1H-4-methylimidazol-1-yl)-pyrimidine 1412956-89-8 C11H14N4O
4-Hydroxy-2-(iso-propyl)-6-(4-tetrahydropyranyl)pyrimidine 4-Hydroxy-2-(iso-propyl)-6-(4-tetrahydropyranyl)pyrimidine 1412958-05-4 C12H18N2O2
4-Hydroxy-2-(iso-propyl)-6-(tert-butoxy)pyrimidine 4-Hydroxy-2-(iso-propyl)-6-(tert-butoxy)pyrimidine 1412958-06-5 C11H18N2O2
4-Hydroxy-2-cyclopropyl-6-(3-thienyl)pyrimidine 4-Hydroxy-2-cyclopropyl-6-(3-thienyl)pyrimidine 1412953-07-1 C11H10N2OS
4-Hydroxy-2-cyclopropyl-6-(imidazol-1-yl)pyrimidine 4-Hydroxy-2-cyclopropyl-6-(imidazol-1-yl)pyrimidine 1412956-09-2 C10H10N4O
4-hydroxy-2-methyl-6-(2-methylpiperidin-1-yl)pyrimidine 4-hydroxy-2-methyl-6-(2-methylpiperidin-1-yl)pyrimidine 1412955-39-5 C11H17N3O
4-Hydroxy-2-methyl-6-(iso-propoxy)pyrimidine 4-Hydroxy-2-methyl-6-(iso-propoxy)pyrimidine 38249-36-4 C8H12N2O2
5-(1H-Pyridin-2-one)pyridine-3-boronic acid pinacol ester 5-(1H-Pyridin-2-one)pyridine-3-boronic acid pinacol ester 1402172-63-7 C16H19BN2O3
5-(2-Methoxyphenyl)pyridine-2-boronic acid pinacol ester 5-(2-Methoxyphenyl)pyridine-2-boronic acid pinacol ester 1402226-80-5 C18H22BNO3
5-(3, 5-Difluorophenyl)pyridine-3-boronic acid pinacol ester 5-(3, 5-Difluorophenyl)pyridine-3-boronic acid pinacol ester 1402227-57-9 C17H18BF2NO2
5-(3-Chlorophenyl)pyridine-3-boronic acid pinacol ester 5-(3-Chlorophenyl)pyridine-3-boronic acid pinacol ester 1402227-41-1 C17H19BClNO2
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(3-(trifluoromethyl)phenyl)thiazole 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(3-(trifluoromethyl)phenyl)thiazole 1402237-80-2 C16H17BF3NO2S
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2-d 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2-d 2241867-62-7 C10H14BDN2O2
5-(4-Tolyl)pyridine-2-boronic acid pinacol ester 5-(4-Tolyl)pyridine-2-boronic acid pinacol ester 1402166-78-2 C18H22BNO2
5-(4-Trfluoromethylphenyl)pyridine-2-boronic acid pinacol ester 5-(4-Trfluoromethylphenyl)pyridine-2-boronic acid pinacol ester 1402233-65-1 C18H19BF3NO2
5-(5-pyrimidyl)pyridine-3-boronic acid pinacol ester 5-(5-pyrimidyl)pyridine-3-boronic acid pinacol ester 2223051-18-9 C15H18BN3O2
5-(6-Chloro-3-pyridyl)pyridine-2-boronic acid pinacol ester 5-(6-Chloro-3-pyridyl)pyridine-2-boronic acid pinacol ester 1402227-50-2 C16H18BClN2O2
5-(cyclopropyl)-4-chloropyridine-3-boronic acid pinacol ester 5-(cyclopropyl)-4-chloropyridine-3-boronic acid pinacol ester 2223052-23-9 C14H19BClNO2
5-Bromo-2-(2-chlorophenyl)pyrimidine 5-Bromo-2-(2-chlorophenyl)pyrimidine 1119089-12-1 C10H6BrClN2
5-Bromo-2-(4-cyanophenyl)pyrimidine 5-Bromo-2-(4-cyanophenyl)pyrimidine 183437-86-7 C11H6BrN3
5-Bromo-2-(methylethylamino)thiazole 5-Bromo-2-(methylethylamino)thiazole 959240-10-9 C6H9BrN2S
5-Bromo-2-amino-4-(2-furyl)pyridine 5-Bromo-2-amino-4-(2-furyl)pyridine 1381936-05-5 C9H7BrN2O
5-Bromo-2-amino-4-(3-hydroxypiperidin-1-yl)pyridine 5-Bromo-2-amino-4-(3-hydroxypiperidin-1-yl)pyridine 1381938-12-0 C10H14BrN3O
5-Bromo-2-ethylpyridine-3-boronic acid pinacol ester 5-Bromo-2-ethylpyridine-3-boronic acid pinacol ester 2223033-17-6 C13H19BBrNO2
5-Bromo-3-(oxan-4-yl)-2-(trifluoromethyl)pyridine 5-Bromo-3-(oxan-4-yl)-2-(trifluoromethyl)pyridine 1622839-97-7 C11H11BrF3NO
5-Bromo-4-(morpholino)pyridine-2-boronic acid pinacol ester 5-Bromo-4-(morpholino)pyridine-2-boronic acid pinacol ester 2223044-85-5 C15H22BBrN2O3
5-Bromo-4-(piperidino)pyridine-2-boronic acid pinacol ester 5-Bromo-4-(piperidino)pyridine-2-boronic acid pinacol ester 2223027-30-1 C16H24BBrN2O2
5-Bromo-6-(4-fluorophenyl)pyridine-3-boronic acid pinacol ester 5-Bromo-6-(4-fluorophenyl)pyridine-3-boronic acid pinacol ester 2223054-53-1 C17H18BBrFNO2
5-Bromo-6-(4-methylimidazol-1-yl)pyridine-3-boronic acid pinacol ester 5-Bromo-6-(4-methylimidazol-1-yl)pyridine-3-boronic acid pinacol ester 1351231-47-4 C15H19BBrN3O2
5-Cyclopropyl-2-(methoxycarbonyl)pyridine-4-boronic acid pinacol ester 5-Cyclopropyl-2-(methoxycarbonyl)pyridine-4-boronic acid pinacol ester 2223035-38-7 C16H22BNO4
5-Ethyl-2-(methoxycarbonyl)pyridine-4-boronic acid pinacol ester 5-Ethyl-2-(methoxycarbonyl)pyridine-4-boronic acid pinacol ester 2223011-37-6 C15H22BNO4
5-Fluoro-2-(4-methyl-1H-pyrazol-1-yl)pyridine-4-boronic acid pinacol ester 5-Fluoro-2-(4-methyl-1H-pyrazol-1-yl)pyridine-4-boronic acid pinacol ester 2223011-45-6 C15H19BFN3O2
5-Fluoro-2-(thiazol-4-yl)pyridine-4-boronic acid pinacol ester 5-Fluoro-2-(thiazol-4-yl)pyridine-4-boronic acid pinacol ester 2223035-19-4 C14H16BFN2O2S
4,7-dibromo-5,6-dinitro-2-octyl-2H-benzo[d][1,2,3]triazole 4,7-dibromo-5,6-dinitro-2-octyl-2H-benzo[d][1,2,3]triazole 1870070-11-3 C14H17Br2N5O4
1H-Pyrazole, 3-bromo-1-(triphenylmethyl)- 1H-Pyrazole, 3-bromo-1-(triphenylmethyl)- 786700-20-7 C22H17BrN2
2-bromo-6-(3-methylpiperidin-1-yl)pyridine-3,4,5-d3 2-bromo-6-(3-methylpiperidin-1-yl)pyridine-3,4,5-d3 2363780-94-1 C11H12BrD3N2
Pyridine, 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]- Pyridine, 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]- 2223029-51-2 C14H18BN3O2
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