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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
1,3-DIMETHYL-1H-PYRAZOLE-5-CARBONITRILE 1,3-DIMETHYL-1H-PYRAZOLE-5-CARBONITRILE 306936-77-6 C6H7N3
2-{5H,6H,7H,8H,9H-[1,2,4]triazolo[4,3-a]azepin-3-yl}pyrrolidine 2-{5H,6H,7H,8H,9H-[1,2,4]triazolo[4,3-a]azepin-3-yl}pyrrolidine 923690-18-0 C11H18N4
4-chloro-6-(2,2,2-trifluoroethyl)thieno[3,2-d]pyrimidine 4-chloro-6-(2,2,2-trifluoroethyl)thieno[3,2-d]pyrimidine 2102553-51-3 C8H4ClF3N2S
Fluclotizolam Fluclotizolam 54123-15-8 C15H10ClFN4S
4-(4-(cyclopentyloxy)quinolin-2-yl)benzene-1,2-diol 4-(4-(cyclopentyloxy)quinolin-2-yl)benzene-1,2-diol 1353224-53-9 C20H19NO3
4-Pyrimidinamine, 5,6-dichloro-N-methyl- 4-Pyrimidinamine, 5,6-dichloro-N-methyl- 1428252-93-0 C5H5Cl2N3
2-(6-Methoxy-naphthalen-1-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 2-(6-Methoxy-naphthalen-1-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 588717-94-6 C17H21BO3
(2,5-dioxopyrrolidin-1-yl) (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(phenylmethoxycarbonylamino)pentanoate (2,5-dioxopyrrolidin-1-yl) (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(phenylmethoxycarbonylamino)pentanoate 57225-26-0 C22H29N3O8
Ethyl 1-Methyl-2,4-dioxo-1H,2H,3H,4H-pyrido[2,3-d]pyrimidine-7-carboxylate Ethyl 1-Methyl-2,4-dioxo-1H,2H,3H,4H-pyrido[2,3-d]pyrimidine-7-carboxylate 1000932-39-7 C11H11N3O4
5-(Benzyloxy)-1,2-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid 5-(Benzyloxy)-1,2-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxylic acid 389130-68-1 C14H14N2O4
4-(propan-2-yl)pyrimidin-5-amine dihydrochloride 4-(propan-2-yl)pyrimidin-5-amine dihydrochloride 2241139-74-0 C7H12ClN3
1,3-Dioxolane 1,3-Dioxolane 646-06-0 C3H6O2
5-ISOXAZOLEMETHANOL 5-ISOXAZOLEMETHANOL 98019-60-4 C4H5NO2
Boron trifluoride tetrahydrofuran complex Boron trifluoride tetrahydrofuran complex 462-34-0 C4H8BF3O
Oxazole-4-carbonitrile Oxazole-4-carbonitrile 55242-84-7 C4H2N2O
PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE 159326-68-8 C6H6N4
OXOTREMORINE SESQUIFUMARATE OXOTREMORINE SESQUIFUMARATE 17360-35-9 C36H48N4O14
2,4,4-TRIMETHYL-2-OXAZOLINE 2,4,4-TRIMETHYL-2-OXAZOLINE 1772-43-6 C6H11NO
(S)-4,5-DIHYDRO-2-(2-((S)-4,5-DIHYDRO-4-ISOPROPYLOXAZOL-2-YL)PROPAN-2-YL)-4-ISOPROPYLOXAZOLE (S)-4,5-DIHYDRO-2-(2-((S)-4,5-DIHYDRO-4-ISOPROPYLOXAZOL-2-YL)PROPAN-2-YL)-4-ISOPROPYLOXAZOLE 131833-92-6 C15H26N2O2
3-Hydroxy-2-bromo-6-trifluoromethylpyridine 3-Hydroxy-2-bromo-6-trifluoromethylpyridine 1211526-50-9 C6H3BrF3NO
2-chloro-3-(trifluoromethyl)pyridine 1-oxide 2-chloro-3-(trifluoromethyl)pyridine 1-oxide 164464-57-7 C6H3ClF3NO
5-bromo-4-(2-fluoropropan-2-yl)pyrimidine 5-bromo-4-(2-fluoropropan-2-yl)pyrimidine 1823944-93-9 C7H8BrFN2
3-bromo-1-methyl-1H-Pyrrolo[2,3-c]pyridine 3-bromo-1-methyl-1H-Pyrrolo[2,3-c]pyridine 956003-06-8 C8H7BrN2
exo-8-boc-8-azabicyclo[3.2.1]octan-2-amine exo-8-boc-8-azabicyclo[3.2.1]octan-2-amine 1408074-65-6 C12H22N2O2
6-bromo-5-methyl-1H-imidazo[4,5-b]pyridine 6-bromo-5-methyl-1H-imidazo[4,5-b]pyridine 28279-41-6 C7H6BrN3
(-)-Menthyl (+)-2-pyrrolidone-5-carboxylate (-)-Menthyl (+)-2-pyrrolidone-5-carboxylate 68127-22-0 C15H25NO3
N-(6-amino-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-5-pyrimidinyl)formamide N-(6-amino-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-5-pyrimidinyl)formamide 14785-95-6 C6H8N4O3
2,4,5-trimethylpyridine 2,4,5-trimethylpyridine 1122-39-0 C8H11N
4-methyloxazole 4-methyloxazole 693-93-6 C4H5NO
4-Thiazolecarboxylic acid 4-Thiazolecarboxylic acid 3973-08-8 C4H3NO2S
2-ISOPROPYL-4(5)-NITROIMIDAZOLE 2-ISOPROPYL-4(5)-NITROIMIDAZOLE 13373-32-5 C6H9N3O2
(2R,4S)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-((S)-1-(4-(4-methylthiazol-5-yl)phenyl)ethyl)pyrrolidine-2-carboxamide hydrochloride (2R,4S)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-((S)-1-(4-(4-methylthiazol-5-yl)phenyl)ethyl)pyrrolidine-2-carboxamide hydrochloride
2H-IMIDAZO[4,5-B]PYRAZIN-2-ONE, 1,3-DIHYDRO- 2H-IMIDAZO[4,5-B]PYRAZIN-2-ONE, 1,3-DIHYDRO- 16328-63-5 C5H4N4O
6-METHYL-2-(PIPERIDIN-4-YL)-1H-BENZO[D]IMIDAZOLE 6-METHYL-2-(PIPERIDIN-4-YL)-1H-BENZO[D]IMIDAZOLE 295790-48-6 C13H17N3
1,6-Diazabicyclo[3.2.1]octane-2-carboxylic acid, 7-oxo-6-(sulfooxy)-, 2-[2-[(3S)-3-pyrrolidinylcarbonyl]hydrazide], (1R,2S,5R)- 1,6-Diazabicyclo[3.2.1]octane-2-carboxylic acid, 7-oxo-6-(sulfooxy)-, 2-[2-[(3S)-3-pyrrolidinylcarbonyl]hydrazide], (1R,2S,5R)- 1452460-79-5 C12H19N5O7S
1-METHYL-1H-BENZOIMIDAZOL-5-YLAMINE TRIHYDROCHLORIDE 1-METHYL-1H-BENZOIMIDAZOL-5-YLAMINE TRIHYDROCHLORIDE 10394-38-4 C8H9N3
2,4(1H,3H)-Pyrimidinedione, 1-cyclopentyl- 2,4(1H,3H)-Pyrimidinedione, 1-cyclopentyl- 13345-72-7 C9H12N2O2
3-(TRIFLUOROMETHYL)-5-P-TOLYL-1H-PYRAZOLE 3-(TRIFLUOROMETHYL)-5-P-TOLYL-1H-PYRAZOLE 26974-15-2 C11H9F3N2
5-Methyl-5-veratrylhydantoin 5-Methyl-5-veratrylhydantoin 892-02-4 C13H16N2O4
QUINAZOLINE, 4-CHLORO-6-FLUORO-2-(TRIFLUOROMETHYL)- QUINAZOLINE, 4-CHLORO-6-FLUORO-2-(TRIFLUOROMETHYL)- 959238-11-0 C9H3ClF4N2
1-benzoylpyrrolidin-2-one 1-benzoylpyrrolidin-2-one 2399-66-8 C11H11NO2
4,6-DICHLORO-2-PYRROLIDIN-1-YL-PYRIMIDINE 4,6-DICHLORO-2-PYRROLIDIN-1-YL-PYRIMIDINE 154117-91-6 C8H9Cl2N3
3-(1-methylethyl)-pyrazole 3-(1-methylethyl)-pyrazole 49633-25-2 C6H10N2
1-(3S)-3-Pyrrolidinyl-piperidine 1-(3S)-3-Pyrrolidinyl-piperidine 917560-78-2 C9H18N2
2-bromo-5-phenyl-1,3-oxazole 2-bromo-5-phenyl-1,3-oxazole 129053-70-9 C9H6BrNO
3-Aminopyrrolidin-2-one hydrochloride 3-Aminopyrrolidin-2-one hydrochloride 117879-49-9 C4H8N2O.ClH
2,5-Diphenylfuran 2,5-Diphenylfuran 955-83-9 C16H12O
5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carbonitrile 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carbonitrile 43024-16-4 C9H8N4
5-Chlorobenzo[b]phosphindole 5-Chlorobenzo[b]phosphindole 33300-85-5 C12H8ClP
5-CHLORO (1H)INDAZOLE 5-CHLORO (1H)INDAZOLE 698-26-0 C7H5ClN2
(3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol (3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol 5605-46-9 C12H17NO4S
2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3S,4S)- 2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3S,4S)- 905854-03-7 C23H19N3O2
ethyl 7-(difluoromethyl)-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylate ethyl 7-(difluoromethyl)-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylate 438219-16-0 C16H13F2N3O2
2-CHLORO-5,6-DIMETHYLBENZIMIDAZOLE 2-CHLORO-5,6-DIMETHYLBENZIMIDAZOLE 39791-96-3 C9H9ClN2
1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazole 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazole 1607838-14-1 C16H21BN2O2
ETHYL 8-CHLORO-6-(TRIFLUOROMETHYL)IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLATE ETHYL 8-CHLORO-6-(TRIFLUOROMETHYL)IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLATE 353258-31-8 C11H8ClF3N2O2
7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline 7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline 1083325-87-4 C12H9BrN4
9-(biphenyl-3-yl)-carbazol-3-yl boronic acid 9-(biphenyl-3-yl)-carbazol-3-yl boronic acid 1416814-68-0 C24H18BNO2
1-methyl-4-aminoimidazole-2-carboxylic acid methyl ester hydrochloride 1-methyl-4-aminoimidazole-2-carboxylic acid methyl ester hydrochloride 480433-71-4 C6H10ClN3O2
5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide 1272353-82-8 C25H20N6O2S
1-Pyrrolidinecarboxylic acid, 2-[(5-bromo-1H-indol-3-yl)carbonyl]-, phenylmethyl ester, (S)- 1-Pyrrolidinecarboxylic acid, 2-[(5-bromo-1H-indol-3-yl)carbonyl]-, phenylmethyl ester, (S)- 199659-03-5 C21H19BrN2O3
3-Bromo-6-(trifluoromethyl)pyridine-2-carbaldehyde 3-Bromo-6-(trifluoromethyl)pyridine-2-carbaldehyde 1227573-28-5 C7H3BrF3NO
5-(Hydroxymethyl)-1-methyl-1H-pyrazole 5-(Hydroxymethyl)-1-methyl-1H-pyrazole 84547-61-5 C5H8N2O
Dimethylmethoxy chromanol Dimethylmethoxy chromanol 83923-51-7 C12H16O3
2,2'-Bi-1H-imidazole, 4,4',5,5'-tetrahydro-4,4'-bis(1-methylethyl)-1,1'-bis(3-methylphenyl)-, (4S,4'S)- 2,2'-Bi-1H-imidazole, 4,4',5,5'-tetrahydro-4,4'-bis(1-methylethyl)-1,1'-bis(3-methylphenyl)-, (4S,4'S)- 2374958-85-5 C26H34N4
Pyrrolidine, 4-fluoro-2-methyl-, hydrochloride (1:1), (2R,4R)- Pyrrolidine, 4-fluoro-2-methyl-, hydrochloride (1:1), (2R,4R)- 2300174-87-0 C5H11ClFN
6-BROMO-2,4-DICHLOROQUINAZOLINE 6-BROMO-2,4-DICHLOROQUINAZOLINE 102393-82-8 C8H3BrCl2N2
Imidazo[1,2-a]pyridine-2-carboxaldehyde, 8-methyl- (9CI) Imidazo[1,2-a]pyridine-2-carboxaldehyde, 8-methyl- (9CI) 143982-39-2 C9H8N2O
Quinazoline, 4-methyl- (6CI,7CI,8CI,9CI) Quinazoline, 4-methyl- (6CI,7CI,8CI,9CI) 700-46-9 C9H8N2
3-Pyrrolidinol, 3-[(3-bromo-5-fluorophenyl)methyl]- 3-Pyrrolidinol, 3-[(3-bromo-5-fluorophenyl)methyl]- 1515119-28-4 C11H13BrFNO
1-Propanone, 1-(2-pyrimidinyl)- (9CI) 1-Propanone, 1-(2-pyrimidinyl)- (9CI) 54643-09-3 C7H8N2O
2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)- (9CI) 2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)- (9CI) 274901-37-0 C7H9ClN2O
1-(3,4-dimethyl-1H-pyrazol-1-yl)ethan-1-one 1-(3,4-dimethyl-1H-pyrazol-1-yl)ethan-1-one 856064-45-4 C7H10N2O
Sodium benzotriazole Sodium benzotriazole
Pyrrolidinone, dimethyl- Pyrrolidinone, dimethyl- 60544-40-3
1,2,4-triazole potassium salt 1,2,4-triazole potassium salt C2H2KN3
1-(diethoxyMethyl)-4,5-diMethyl-1H-iMidazole 1-(diethoxyMethyl)-4,5-diMethyl-1H-iMidazole 74483-00-4 C10H18N2O2
1-(Phenylsulfonyl)-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine 1-(Phenylsulfonyl)-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine 1174038-65-3 C19H21BN2O4S
1,3-diMethyliMidazoliuM dicyanaMide 1,3-diMethyliMidazoliuM dicyanaMide 869301-19-9 C7H9N5
1-tert-Butyl-1H-pyrazole 1-tert-Butyl-1H-pyrazole 15754-60-6 C7H12N2
1-(3-Methoxypropyl)-4-piperidinamine 1-(3-Methoxypropyl)-4-piperidinamine 179474-79-4 C9H20N2O
1-tert-butyl-3-phenyl-1H-pyrazole 1-tert-butyl-3-phenyl-1H-pyrazole 1269293-29-9 C13H16N2
1H-Pyrazolo[4,3-b]pyridine-6-carboxylicacid 1H-Pyrazolo[4,3-b]pyridine-6-carboxylicacid 1256807-59-6 C7H5N3O2
2-broMo-5-Methyl-oxazole 2-broMo-5-Methyl-oxazole 129053-67-4 C4H4BrNO
IMidazo[1,2-a]pyridin-8-aMine, 5-broMo- IMidazo[1,2-a]pyridin-8-aMine, 5-broMo- 1357947-00-2 C7H6BrN3
IMidazo[1,2-a]pyridine-2-carboxylic acid, 7-chloro- IMidazo[1,2-a]pyridine-2-carboxylic acid, 7-chloro- 1020038-42-9 C8H5ClN2O2
4-chloro-2-fluoro-5-iodopyridine 4-chloro-2-fluoro-5-iodopyridine 1184914-20-2 C5H2ClFIN
(S)-N-(Pyrrolidin-3-yl)acetaMide hydrochloride (S)-N-(Pyrrolidin-3-yl)acetaMide hydrochloride 1246277-44-0 C6H13ClN2O
3-fluoro-4-(4-Methyl-1H-iMidazol-1-yl)benzoic acid 3-fluoro-4-(4-Methyl-1H-iMidazol-1-yl)benzoic acid 1243205-04-0 C11H9FN2O2
3-(1-chloroH-pyrrolo[1,2-a]pyrazin-6-yl)cyclobutanone 3-(1-chloroH-pyrrolo[1,2-a]pyrazin-6-yl)cyclobutanone 936901-72-3 C10H8ClN3O
N-Cyclopropyl-3-oxetanamine N-Cyclopropyl-3-oxetanamine 1340518-89-9 C6H11NO
[2,2'-Bipyridine]-4,4'-dicarboxylic acid [2,2'-Bipyridine]-4,4'-dicarboxylic acid 117330-40-2 C16H16N2O4
8-BroMo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine 8-BroMo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine 643067-83-8 C7H6BrNO2
2-Ethyl-2-oxazoline 2-Ethyl-2-oxazoline 10431-98-8 C5H9NO
1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]iMidazol-2(3H)-one 1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]iMidazol-2(3H)-one 1187968-73-5 C14H19BN2O3
8-BroMo-3-iodo-iMidazo[1,2-a]pyridine 8-BroMo-3-iodo-iMidazo[1,2-a]pyridine 1232038-69-5 C7H4BrIN2
N-(4-Nitrophenyl)-4-(3-pyridyl)-2-pyriMidineaMine N-(4-Nitrophenyl)-4-(3-pyridyl)-2-pyriMidineaMine 181065-58-7 C15H11N5O2
3-(2-chloropyriMidin-4-yl)-1-Methylindole 3-(2-chloropyriMidin-4-yl)-1-Methylindole 1032452-86-0 C13H10ClN3
MMB-2201 MMB-2201 1616253-26-9 C20H27FN2O3
1,2,4-Triazolylsodium 1,2,4-Triazolylsodium 41253-21-8 C2H4N3Na
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