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Heterocyclic Compounds

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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:
4-TrifluoroMethyl-pyridine-3-carbaldehyde
CAS:
1083197-78-7
MF:
C7H4F3NO
Structure:
Chemical Name:
Imidazo[1,2-a]pyridine-7-carbonitrile
CAS:
952566-04-0
MF:
C8H5N3
Structure:
Chemical Name:
4-Chloro-2-Methyl-6-phenyl-5H-pyrrolo[3,2-d]pyriMidine
CAS:
52617-71-7
MF:
C13H10ClN3
Structure:
Chemical Name:
4,6-dichloropyriMidine-2-carbonitrile
CAS:
1451391-83-5
MF:
C5HCl2N3
Structure:
Chemical Name:
81438-40-6
CAS:
81438-40-6
MF:
C9H12N2O2
Structure:
Chemical Name:
Uridine, 4',5'-didehydro-5'-deoxy-
CAS:
14365-63-0
MF:
C9H10N2O5
Structure:
Chemical Name:
5-BroMo-2,3-dihydroiMidazo[1,2-a]pyrazine
CAS:
1449117-44-5
MF:
C6H6BrN3
Structure:
Chemical Name:
7-Chloro-iMidazo[1,2-a]pyridine-2-carbaldehyde
CAS:
1020034-59-6
MF:
C8H5ClN2O
Structure:
Chemical Name:
Ethyl 3-(2-(((4-carbaMiMidoylphenyl)aMino)Methyl)-1-Methyl-N-(pyridin-2-yl)-1H-benzo[d]iMidazole-5-carboxaMido)propanoate acetate
CAS:
1188263-64-0
MF:
C29H33N7O4
Structure:
Chemical Name:
Methyl azepane-4-carboxylate hydrochloride
CAS:
1383132-15-7
MF:
C8H16ClNO2
Structure:
Chemical Name:
(3R,5S)-5-Methylpyrrolidin-3-ol
CAS:
1108234-23-6
MF:
C5H11NO
Structure:
Chemical Name:
2-Butyl-2,3-dihydrothieno[3,4-b]-1,4-dioxine
CAS:
552857-06-4
MF:
C10H14O2S
Structure:
Chemical Name:
(S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile
CAS:
1448440-39-8
MF:
C7H9F2N3O
Structure:
Chemical Name:
5,6,7,8-Tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid ethyl ester
CAS:
951627-01-3
MF:
C9H13N3O2
Structure:
Chemical Name:
Isopropyl 1H-imidazole-1-carboxylate
CAS:
82998-18-3
MF:
C7H10N2O2
Structure:
Chemical Name:
Di-Fluoro ethylene carbonate
CAS:
311810-76-1
MF:
C3H2F2O3
Structure:
Chemical Name:
AKOS B019512
CAS:
5775-82-6
MF:
C5H7BrN2
Structure:
Chemical Name:
(S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE
CAS:
118949-61-4
MF:
C17H23N3O2
Structure:
Chemical Name:
6-CHLORO-4-NITRO-1H-INDAZOLE
CAS:
885519-50-6
MF:
C7H4ClN3O2
Structure:
Chemical Name:
3-tert-Butoxycarbonylphenylboronic acid
CAS:
220210-56-0
MF:
C11H15BO4
Structure:
Chemical Name:
Phosphonium, [(3'R)-1'-[(1,1-dimethylethoxy)carbonyl]-2-oxo[1,3'-bipyrrolidin]-3-yl]triphenyl-, bromide
CAS:
376653-42-8
MF:
C31H36BrN2O3P
Structure:
Chemical Name:
4,4'-Difluorodiphenylketone-3,3'-disulfonic acid
CAS:
625392-06-5
MF:
C13H8F2O7S2
Structure:
Chemical Name:
7'-brmomspiro[fluorene-9,5'-indeno[1,2-b]pyridine]
CAS:
1666128-76-2
MF:
C24H14BrN
Structure:
Chemical Name:
5-bromo-4-chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine
CAS:
1477532-48-1
MF:
C7H3BrClN3O2
Structure:
Chemical Name:
8-Ethyl-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-8H-pyrido[2,3-d]pyrimidin-7-one
CAS:
211245-14-6
MF:
C20H24N6O
Structure:
Chemical Name:
(3S,5R)-5-methylpyrrolidin-3-ol hydrochloride
CAS:
1107658-78-5
MF:
C5H12ClNO
Structure:
Chemical Name:
(R)-4-(2-chloro-6-(methylthiomethyl)pyrimidin-4-yl)-3-methylmorpholine
CAS:
1352227-15-6
MF:
C11H16ClN3OS
Structure:
Chemical Name:
2-(5-(4-amino-2-fluoro-5-nitro-3-(tetrahydrofuran-2-yl)phenyl)pyrimidin-2-yl)propan-2-ol
CAS:
1384984-28-4
MF:
C17H19FN4O4
Structure:
Chemical Name:
5-bromo-2-hydrazinylpyridine hydrochloride
CAS:
1295647-30-1
MF:
C5H7BrClN3
Structure:
Chemical Name:
3,3-DIMETHYLPYRROLIDINE-2-CARBOXYLIC ACID hydrochloride
CAS:
61406-78-8
MF:
C7H14ClNO2
Structure:
Chemical Name:
6-Bromoindole-3-carboxylic acid
CAS:
101774-27-0
MF:
C9H6BrNO2
Structure:
Chemical Name:
4-Bromo-1,3,5-trimethyl-1H-pyrazole
CAS:
15801-69-1
MF:
C6H9BrN2
Structure:
Chemical Name:
2-Boc-3,4-dihydro-1H-pyrrolo-[1,2-a]pyrazine-6-carboxylic acid
CAS:
1363380-86-2
MF:
C13H18N2O4
Structure:
Chemical Name:
(S)-3-(PYRROLIDIN-2-YL)PYRIDINE DIHYDROCHLORIDE
CAS:
287966-92-1
MF:
C9H14Cl2N2
Structure:
Chemical Name:
3-(difluoromethyl)pyrrolidine hydrochloride
CAS:
1376176-56-5
MF:
C5H10ClF2N
Structure:
Chemical Name:
Chloro[1,3-bis(cyclohexyl)2H-imidazol-2-ylidene]gold(I), 98%
CAS:
852445-87-5
MF:
C15H24AuClN2
Structure:
Chemical Name:
4,4'-((3',4',5',6'-tetrakis(4-(pyridin-4-ylethynyl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-diyl)bis(ethyne-2,1-diyl))dipyridine
CAS:
591215-25-7
MF:
C84H48N6
Structure:
Chemical Name:
ffBTZ-C8-2Br
CAS:
1393528-97-6
MF:
C14H17Br2F2N3
Structure:
Chemical Name:
4-Chloro-2-iodo-5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine
CAS:
1420885-94-4
MF:
C14H17ClF3IN2OSi
Structure:
Chemical Name:
3,6-DI-4-PYRIDYL-1,2,4,5-TETRAZINE
CAS:
57654-36-1
MF:
C12H8N6
Structure:
Chemical Name:
ETHYL 5-ACETYLISOXASOLE-3-CARBOXYLATE
CAS:
104776-70-7
MF:
C8H9NO4
Chemical Name:
Poly-p-xylylene
CAS:
25722-33-2
Structure:
Chemical Name:
5-thien-2-yl-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-2-carbohydrazide
CAS:
832739-24-9
MF:
C12H12F3N5OS
Structure:
Chemical Name:
4,6-dibromo-2-methylpyrimidine
CAS:
1598222-27-5
MF:
C5H4Br2N2
Structure:
Chemical Name:
3-fluoro-4-(pyrrolidin-1-ylmethyl)benzaldehyde
CAS:
1443353-89-6
MF:
C12H14FNO
Structure:
Chemical Name:
C-(1-BENZYL-PYRROLIDIN-3-YL)-METHYLAMINE
CAS:
93138-61-5
MF:
C12H18N2
Structure:
Chemical Name:
PPT
CAS:
263717-53-9
MF:
C24H22N2O3
Structure:
Chemical Name:
6-FLUOROPYRIDINE-2-SULFONYL CHLORIDE
CAS:
128583-07-3
MF:
C5H3ClFNO2S
Structure:
Chemical Name:
BENZO[4,5]IMIDAZO[1,2-A][1,3,5]TRIAZIN-2-YLAMINE
CAS:
61678-05-5
MF:
C9H7N5
Structure:
Chemical Name:
METHYL 2-(METHYLTHIO)PYRIMIDINE-4-CARBOXYLATE
CAS:
64224-67-5
MF:
C7H8N2O2S
Structure:
Chemical Name:
1-[(3S)-3-PYRROLIDINYL]-PIPERIDINE DIHYDROCHLORIDE
CAS:
917505-12-5
MF:
C9H19ClN2
Structure:
Chemical Name:
4-AMINO-5-BROMO-6-ETHOXYPICOLINIC ACID
CAS:
1057260-48-6
MF:
C8H9BrN2O3
Structure:
Chemical Name:
5-bromo-1H-pyrrolo[2,3-c] pyridine-2-carboxylic acid
CAS:
800401-71-2
MF:
C8H5BrN2O2
Structure:
Chemical Name:
2,4-Dichloro-7-cyanoquinazoline
CAS:
864292-40-0
MF:
C9H3Cl2N3
Structure:
Chemical Name:
Pyrrolidine, 2-[bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilyl)oxy]methyl]-, (2R)-
CAS:
908303-26-4
MF:
C24H23F12NOSi
Structure:
Chemical Name:
2,4,6-Trichloro-pyrido[3,2-d]pyrimidine
CAS:
1036738-12-1
MF:
C7H2Cl3N3
Structure:
Chemical Name:
3-Amino-1-methylpiperidine dihydrochloride
CAS:
894808-73-2
MF:
C6H15ClN2
Structure:
Chemical Name:
(3S,4R)-1-benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid
CAS:
80909-49-5
MF:
C18H18FNO2
Structure:
Chemical Name:
(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide
CAS:
473727-83-2
MF:
C21H23N3O5
Structure:
Chemical Name:
1-Pyrrolidinecarboxaldehyde, 2-oxo-
CAS:
40321-44-6
MF:
C5H7NO2
Structure:
Chemical Name:
6-chloropyrido[3,2-d]pyrimidin-4(3H)-one
CAS:
171178-33-9
MF:
C7H4ClN3O
Structure:
Chemical Name:
4-broMo-2-(2,6-dichlorophenyl)-7-fluoro-1H-iMidazo[4,5-c]pyridine
CAS:
1334411-83-4
MF:
C12H5BrCl2FN3
Structure:
Chemical Name:
5-BroMo-2-chloro-6-MethylpyriMidin-4-aMine
CAS:
54093-23-1
MF:
C5H5BrClN3
Structure:
Chemical Name:
3-(BroMoMethyl)-1H-pyrrolo[2,3-b]pyridine
CAS:
1174007-40-9
MF:
C8H7BrN2
Structure:
Chemical Name:
2-Chloro-4-(trifluoromethyl)nicotinonitrile
CAS:
896447-72-6
MF:
C7H2ClF3N2
Structure:
Chemical Name:
3-fluoro-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine hydrochloride
CAS:
1346808-65-8
MF:
C7H8ClFN2
Structure:
Chemical Name:
5-Fluoro-3,4-dihydro-2,4-dioxo-1(2H)-PyriMidineacetic Acid
CAS:
56059-30-4
MF:
C6H5FN2O4
Structure:
Chemical Name:
TribroMocyanuric acid
CAS:
17497-85-7
MF:
C3Br3N3O3
Structure:
Chemical Name:
2-PYRROLIDIN-2-YLPYRIDINE
CAS:
22083-78-9
MF:
C9H12N2
Structure:
Chemical Name:
1-(3-HydroxyMethyl-pyrrolidin-1-yl)-ethanone
CAS:
191347-96-3
MF:
C7H13NO2
Structure:
Chemical Name:
Isopropyl-(4-Methyl-pyriMidin-2-yl)-aMine
CAS:
1341073-92-4
MF:
C8H13N3
Structure:
Chemical Name:
Ethyl 4-Methyl-2-(Methylthio)-6-oxo-1,6-dihydropyriMidine-5-carboxylate
CAS:
344361-90-6
MF:
C9H12N2O3S
Structure:
Chemical Name:
5-(2-AMinopropyl)indole
CAS:
3784-30-3
MF:
C11H14N2
Structure:
Chemical Name:
IMidazo[1,2-a]pyridin-8-aMine, 7-broMo-
CAS:
1357945-44-8
MF:
C7H6BrN3
Structure:
Chemical Name:
1,3-Pyrrolidinedicarboxylic acid, 4-oxo-, 1-(1,1-diMethylethyl) 3-Methyl ester
CAS:
194924-95-3
MF:
C11H17NO5
Structure:
Chemical Name:
tert-butyl octahydro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate
CAS:
1211586-14-9
MF:
C12H22N2O2
Structure:
Chemical Name:
(S)-4-Oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylic acid
CAS:
1190392-22-3
MF:
C8H8N2O3
Structure:
Chemical Name:
1-Methyl-5-oxo-L-Proline
CAS:
52574-06-8
MF:
C6H9NO3
Structure:
Chemical Name:
3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione
CAS:
1239986-50-5
MF:
C23H19N3O2
Structure:
Chemical Name:
5-chloro-7-(3,4-diMethoxyphenyl)iMidazo[1,2-c]pyriMidine
CAS:
371171-20-9
MF:
C14H12ClN3O2
Structure:
Chemical Name:
BenzaMide, N-[2-[[(3R,4R)-1-[cis-4-(1,3-benzodioxol-5-yl)-4-hydroxycyclohexyl]-4-ethoxy-3-pyrrolidinyl]aMino]-2-oxoethyl]-3-(trifluoroMethyl)-, rel-
CAS:
1285539-85-6
MF:
C29H34F3N3O6
Structure:
Chemical Name:
2,4-Dichloro-6-isopropyl-5,6-dihydropyrrolo[3,4-d]pyriMidin-7-one
CAS:
1079649-94-7
MF:
C9H9Cl2N3O
Structure:
Chemical Name:
2,4-Dichloro-6-isopropyl-5,6-dihydropyrrolo[3,4-d]pyriMidin-7-one
CAS:
1079649-94-7
MF:
C9H9Cl2N3O
Structure:
Chemical Name:
2,4-Dichloro-6-isopropyl-5,6-dihydropyrrolo[3,4-d]pyriMidin-7-one
CAS:
1079649-94-7
MF:
C9H9Cl2N3O
Structure:
Chemical Name:
(2-BENZOTHIAZOLYLTHIO)ACETIC ACID
CAS:
6295-57-4
MF:
C9H7NO2S2
Structure:
Chemical Name:
3-[[3,5-bis(trifluoroMethyl)phenyl]aMino]-4-[[(1S,2S)-2-(1-pyrrolidinyl)cyclohexyl]aMino]-
CAS:
1211565-10-4
MF:
C22H23F6N3O2
Structure:
Chemical Name:
2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3R,4R)-rel-
CAS:
905853-99-8
MF:
C23H19N3O2
Structure:
Chemical Name:
CyclopentaneMethanol, 4-(4-chloro-7H-pyrrolo[2,3-d]pyriMidin-7-yl)-2-hydroxy-, (1S,2S,4R)-
CAS:
1113025-27-6
MF:
C12H14ClN3O2
Structure:
Chemical Name:
1-Ethyl-1H-iMidazole-5-carboxylic acid
CAS:
71925-11-6
MF:
C6H8N2O2
Structure:
Chemical Name:
4-Hydroxy-6-Methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile
CAS:
67643-17-8
MF:
C7H6N2O2
Structure:
Chemical Name:
N-[3,5-bis(trifluoroMethyl)phenyl]-N'-[(1R,2R)-2-(1-pyrrolidinyl)cyclohexyl]-Thiourea
CAS:
1314743-49-1
MF:
C19H23F6N3S
Structure:
Chemical Name:
L-Proline sodiuM salt
CAS:
15383-56-9
MF:
C5H10NNaO2
Structure:
Chemical Name:
1H-BenziMidazole-1-acetaMide, 2-phenyl-N-(phenylMethyl)-α-4-piperidinyl-
CAS:
1440753-53-6
MF:
C27H28N4O
Structure:
Chemical Name:
4-Methyl-2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-benzonitrile
CAS:
863868-22-8
MF:
C14H18BNO2
Structure:
Chemical Name:
5-(Pyrrolidin-1-yl)pentan-1-aMine dihydrochloride
CAS:
1624260-73-6
MF:
C9H22Cl2N2
Structure:
Chemical Name:
(2S)-2-(3-BROMOPHENYL)PYRROLIDINE
CAS:
1217694-15-9
MF:
C10H12BrN
Structure:
Chemical Name:
2-AMino-3-(pyrrolidin-3-yl)propanoic acid
CAS:
1313016-75-9
MF:
C7H14N2O2
Structure:
Chemical Name:
6-Methoxy-iMidazo[1,2-b]pyridazine-2-carboxylic acid
CAS:
64068-09-3
MF:
C8H7N3O3
Structure:
Chemical Name:
4,4',4''-(1,3,5-Triazine-2,4,6-triyl)trianiline
CAS:
14544-47-9
MF:
C21H18N6
Structure:
Chemical Name:
1-Ethyl-3-methylimidazolium bis(fluorosulfonyl)imide
CAS:
235789-75-0
MF:
C6H11F2N3O4S2