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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-(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
1-[4-(CHLOROMETHYL)PHENYL]-1H-PYRAZOLE HYDROCHLORIDE 1-[4-(CHLOROMETHYL)PHENYL]-1H-PYRAZOLE HYDROCHLORIDE 143426-52-2 C10H9ClN2
3-(2-ETHYL-IMIDAZOL-1-YLMETHYL)-4-METHOXY-BENZALDEHYDE HYDROCHLORIDE 3-(2-ETHYL-IMIDAZOL-1-YLMETHYL)-4-METHOXY-BENZALDEHYDE HYDROCHLORIDE 1052542-54-7 C14H17ClN2O2
5-(CHLOROMETHYL)-7-ETHOXY-2-(TRIFLUOROMETHYL)[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE 5-(CHLOROMETHYL)-7-ETHOXY-2-(TRIFLUOROMETHYL)[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE 1000932-47-7 C9H8ClF3N4O
3-Amino-1-benzyl-3-cyanopyrrolidine 3-Amino-1-benzyl-3-cyanopyrrolidine 145090-28-4 C12H15N3
3-Boc-6-oxa-3-aza-bicyclo[3.1.0]hexane 3-Boc-6-oxa-3-aza-bicyclo[3.1.0]hexane 114214-49-2 C9H15NO3
Thiazolo[4,5-d]pyrimidin-2(3H)-one, 5-amino- Thiazolo[4,5-d]pyrimidin-2(3H)-one, 5-amino- 848691-22-5 C5H4N4OS
Pyrrolidine, 3-(4-fluorophenyl)-, hydrochloride (1:1) Pyrrolidine, 3-(4-fluorophenyl)-, hydrochloride (1:1) 1029636-03-0 C10H13ClFN
4-N-DECYLPYRIDINE 4-N-DECYLPYRIDINE 1815-99-2 C15H25N
2,6-DICHLORO-N,N-DIETHYLPYRIMIDIN-4-AMINE 2,6-DICHLORO-N,N-DIETHYLPYRIMIDIN-4-AMINE 78418-15-2 C8H11Cl2N3
2-[4-(TRIFLUOROMETHYL)PHENYL]-1H-IMIDAZOLE 2-[4-(TRIFLUOROMETHYL)PHENYL]-1H-IMIDAZOLE 34898-30-1 C10H7F3N2
4-(2-CHLOROACETAMIDO)-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL 4-(2-CHLOROACETAMIDO)-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL 36775-23-2 C11H20ClN2O2*
BOC-GLU(OSU)-OTBU BOC-GLU(OSU)-OTBU 81659-82-7 C18H28N2O8
1-Methyl-1H-indazole-6-carbaldehyde 1-Methyl-1H-indazole-6-carbaldehyde 1092351-51-3 C9H8N2O
4-(4-bromophenyl)-1H-pyrazol-5-amine 4-(4-bromophenyl)-1H-pyrazol-5-amine 57999-08-3 C9H8BrN3
7-chloro-5-(methoxymethyl)[1,2,4]triazolo[1,5-a]pyrimidine 7-chloro-5-(methoxymethyl)[1,2,4]triazolo[1,5-a]pyrimidine 926245-01-4 C7H7ClN4O
2-(4-BROMO-PHENYL)-OXAZOLE 2-(4-BROMO-PHENYL)-OXAZOLE 176961-50-5 C9H6BrNO
1H-Pyrazolo[4,3-d]pyrimidine-5,7(4H,6H)-dione 1H-Pyrazolo[4,3-d]pyrimidine-5,7(4H,6H)-dione 40769-81-1 C5H4N4O2
2-Propylimidazole 2-Propylimidazole 50995-95-4 C6H10N2
2-Fluoropyridine-5-carbonyl chloride ,98% 2-Fluoropyridine-5-carbonyl chloride ,98% C6H3ClFNO
7-Aminopyrazolo[1,5-a]pyrimidine-6-carbonitrile 7-Aminopyrazolo[1,5-a]pyrimidine-6-carbonitrile 89975-57-5 C7H5N5
Ganoderenic acid B Ganoderenic acid B 100665-41-6 C30H42O7
POLY(METHYLSILSESQUIOXANE) POLY(METHYLSILSESQUIOXANE) 68554-70-1 unspecified
3-Nitro-2-naphthol 3-Nitro-2-naphthol 32361-60-7 C10H7NO3
(R)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE (R)-4-PHENYL-1,3-THIAZOLIDINE-2-THIONE 110199-18-3 C9H9NS2
3-(2,3-DICHLOROPHENOXY)PYRROLIDINE HYDROCHLORIDE 3-(2,3-DICHLOROPHENOXY)PYRROLIDINE HYDROCHLORIDE 817187-08-9 C10H12Cl3NO
1-BENZYL-3-METHYLPYRROLIDIN-3-OL 1-BENZYL-3-METHYLPYRROLIDIN-3-OL 96567-93-0 C12H17NO
4-BROMO-1-PROPYL-1H-PYRAZOLE 4-BROMO-1-PROPYL-1H-PYRAZOLE 141302-33-2 C6H9BrN2
(S)-3-METHOXY-PYRROLIDINE HYDROCHLORIDE (S)-3-METHOXY-PYRROLIDINE HYDROCHLORIDE 685828-16-4 C5H12ClNO
6-Bromo-2-(4-methoxyphenyl)imidazo[1,2-a]pyridine 6-Bromo-2-(4-methoxyphenyl)imidazo[1,2-a]pyridine 452967-40-7 C14H11BrN2O
(2s,4s)-dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate (2s,4s)-dibenzyl 4-hydroxypyrrolidine-1,2-dicarboxylate 132592-07-5 C20H21NO5
8-Bromoquinazoline 8-Bromoquinazoline 1123169-41-4 C8H5BrN2
1H-PYRROLO[2,3-B]PYRIDINE-2-CARBOXYLIC ACID 1H-PYRROLO[2,3-B]PYRIDINE-2-CARBOXYLIC ACID 136818-50-3 C8H6N2O2
tert-butyl 5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate
tert-butyl 5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate 345311-03-7 C11H17N3O2
(2S,4R)-4-aminopyrrolidine-2-carboxylic acid dihydrochloride (2S,4R)-4-aminopyrrolidine-2-carboxylic acid dihydrochloride 16257-89-9 C5H10N2O2.2ClH
1,3-Dihydro-6-iodo-3-methyl-2H-imidazo[4,5-b]pyridin-2-one 1,3-Dihydro-6-iodo-3-methyl-2H-imidazo[4,5-b]pyridin-2-one 309742-29-8 C7H6IN3O
2-CARBETHOXY-5-ETHYLINDOLE 2-CARBETHOXY-5-ETHYLINDOLE 37033-94-6 C13H15NO2
3-(2-methoxyethyl)-1H-pyrazol-5-amine 3-(2-methoxyethyl)-1H-pyrazol-5-amine 1187058-44-1 C6H11N3O
MK-3697 MK-3697 1224846-01-8 C23H21N5O3S
5-Bromo-7-methyl-1H-indole 5-Bromo-7-methyl-1H-indole 15936-81-9 C9H8BrN
7-Bromo-1H-benzo[d][1,2,3]triazole 7-Bromo-1H-benzo[d][1,2,3]triazole 1064721-11-4 C6H4BrN3
5-[(4-chlorophenoxy)methyl]-3-[(4-methoxyphenyl)methyl]-1,2,4-oxadiazole 5-[(4-chlorophenoxy)methyl]-3-[(4-methoxyphenyl)methyl]-1,2,4-oxadiazole 6148-18-1 C9H7ClN2
5-Bromo-2,3-dimethylindole 5-Bromo-2,3-dimethylindole 4583-55-5 C10H10BrN
7-Chloro-N-(3-chloro-4-fluorophenyl)-6-nitroquinazolin-4-amine 7-Chloro-N-(3-chloro-4-fluorophenyl)-6-nitroquinazolin-4-amine 179552-73-9 C14H7Cl2FN4O2
3-(trifluoromethyl)-1H-1,2,4-triazole(SALTDATA: FREE) 3-(trifluoromethyl)-1H-1,2,4-triazole(SALTDATA: FREE) 60406-75-9 C3H2F3N3
[(2S,4R)-4-amino-1-methyl-2-pyrrolidinyl]methanol(SALTDATA: FREE) [(2S,4R)-4-amino-1-methyl-2-pyrrolidinyl]methanol(SALTDATA: FREE) 1256636-31-3 C6H14N2O
(R)-3-Amino-pyrrolidin-2-one hydrochloride (R)-3-Amino-pyrrolidin-2-one hydrochloride 223407-19-0 C4H9ClN2O
bis[2-(2-Pyridinyl)phenolato]berylliuM bis[2-(2-Pyridinyl)phenolato]berylliuM 220694-90-6 C22H16BeN2O2
4-chloro-6-fluoro-1H-benzo[d]iMidazole 4-chloro-6-fluoro-1H-benzo[d]iMidazole 1314092-05-1 C7H4ClFN2
1-tert-butyl 3-ethyl pyrrolidine-1,3-dicarboxylate 1-tert-butyl 3-ethyl pyrrolidine-1,3-dicarboxylate 1158751-03-1 C12H21NO4
2-Propenoic acid, 3-(3H-iMidazo[4,5-b]pyridin-6-yl)-, (2E)- 2-Propenoic acid, 3-(3H-iMidazo[4,5-b]pyridin-6-yl)-, (2E)- 335030-65-4 C9H7N3O2
(3S,3'S)-4,4'-(7-chloropyrido[2,3-d]pyriMidine-2,4-diyl)bis(3-MethylMorpholine) (3S,3'S)-4,4'-(7-chloropyrido[2,3-d]pyriMidine-2,4-diyl)bis(3-MethylMorpholine) 1009303-44-9 C17H22ClN5O2
5-Fluoro-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 5-Fluoro-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 1192023-08-7 C14H17BFNO2
1,3-diMethyliMidazoliuM hexafluorophosphate 1,3-diMethyliMidazoliuM hexafluorophosphate 243664-15-5 C5H9F6N2P
1-((S)-2-HydroxyMethyl-pyrrolidin-1-yl)-ethanone 1-((S)-2-HydroxyMethyl-pyrrolidin-1-yl)-ethanone 66158-68-7 C7H13NO2
4-Amino-2,6-dichloropyrimidine-5-carboxaldehyde 4-Amino-2,6-dichloropyrimidine-5-carboxaldehyde 5971-68-6 C5H3Cl2N3O
1-phenyl-1H-pyrazol-5-ol 1-phenyl-1H-pyrazol-5-ol 876-93-7 C9H8N2O
5-broMo-3-(4-Methoxyphenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde 5-broMo-3-(4-Methoxyphenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde 1188037-01-5 C17H13BrN2O2
8-BroMo-2-chloro-6-fluoro-quinazoline 8-BroMo-2-chloro-6-fluoro-quinazoline 953039-63-9 C8H3BrClFN2
Methyl 3-broMo-6-chloropyrazine-2-carboxylate Methyl 3-broMo-6-chloropyrazine-2-carboxylate 13457-28-8 C6H4BrClN2O2
2,4-Dichloro-7,8-dihydro-5H-S,S-di-oxoisothiopyrano[4,3-d]pyriMidine 2,4-Dichloro-7,8-dihydro-5H-S,S-di-oxoisothiopyrano[4,3-d]pyriMidine 1187830-50-7 C7H6Cl2N2O2S
2-Methylsulfonyl-4,6-dichloro-5-ethylpyriMidine 2-Methylsulfonyl-4,6-dichloro-5-ethylpyriMidine 1263314-16-4 C7H8Cl2N2O2S
N-(naphthalen-1-yl)-9,9-diphenyl-9H-fluoren-2-aMine N-(naphthalen-1-yl)-9,9-diphenyl-9H-fluoren-2-aMine 1196694-11-7 C35H25N
1-(11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl- Pyrrolidine 1-(11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl- Pyrrolidine 627528-96-5 C24H20NO2P
3-bis(4-Methylbenzoyloxy)succinate) 3-bis(4-Methylbenzoyloxy)succinate) 477600-71-8 C34H40N2O8
5-b]pyridine 5-b]pyridine 954238-09-6 C8H8BrN3
7-chloroiMidazo[1,2-a]pyriMidin-5(1H)-one 7-chloroiMidazo[1,2-a]pyriMidin-5(1H)-one 57473-33-3 C6H4ClN3O
4-AMino-N-[(1-ethyl-5-oxo-2-pyrrolidinyl)Methyl]-5-(ethylsulfonyl)-2-MethoxybenzaMide 4-AMino-N-[(1-ethyl-5-oxo-2-pyrrolidinyl)Methyl]-5-(ethylsulfonyl)-2-MethoxybenzaMide 1391052-47-3 C17H25N3O5S
(S)-6-(1,3-dihydroxy-1-(1-trityl-1H-iMidazol-4-yl)propyl)-N-Methyl-2-naphthaMide (S)-6-(1,3-dihydroxy-1-(1-trityl-1H-iMidazol-4-yl)propyl)-N-Methyl-2-naphthaMide 566200-79-1 C37H33N3O3
1H-BenziMidazole-5-carboxylic acid, 2-aMino-1-[trans-4-[[(1,1-diMethylethyl)diMethylsilyl]oxy]cyclohexyl]-, ethyl ester 1H-BenziMidazole-5-carboxylic acid, 2-aMino-1-[trans-4-[[(1,1-diMethylethyl)diMethylsilyl]oxy]cyclohexyl]-, ethyl ester 1012104-43-6 C22H35N3O3Si
2,4-dichloro-6-Methyl-5H-pyrrolo[3,2-d]pyriMidine 2,4-dichloro-6-Methyl-5H-pyrrolo[3,2-d]pyriMidine 1196157-27-3 C7H5Cl2N3
4-TrifluoroMethyl-pyridine-3-carbaldehyde 4-TrifluoroMethyl-pyridine-3-carbaldehyde 1083197-78-7 C7H4F3NO
Imidazo[1,2-a]pyridine-7-carbonitrile Imidazo[1,2-a]pyridine-7-carbonitrile 952566-04-0 C8H5N3
4-Chloro-2-Methyl-6-phenyl-5H-pyrrolo[3,2-d]pyriMidine 4-Chloro-2-Methyl-6-phenyl-5H-pyrrolo[3,2-d]pyriMidine 52617-71-7 C13H10ClN3
4,6-dichloropyriMidine-2-carbonitrile 4,6-dichloropyriMidine-2-carbonitrile 1451391-83-5 C5HCl2N3
81438-40-6 81438-40-6 81438-40-6 C9H12N2O2
Uridine, 4',5'-didehydro-5'-deoxy- Uridine, 4',5'-didehydro-5'-deoxy- 14365-63-0 C9H10N2O5
5-BroMo-2,3-dihydroiMidazo[1,2-a]pyrazine 5-BroMo-2,3-dihydroiMidazo[1,2-a]pyrazine 1449117-44-5 C6H6BrN3
7-Chloro-iMidazo[1,2-a]pyridine-2-carbaldehyde 7-Chloro-iMidazo[1,2-a]pyridine-2-carbaldehyde 1020034-59-6 C8H5ClN2O
Ethyl 3-(2-(((4-carbaMiMidoylphenyl)aMino)Methyl)-1-Methyl-N-(pyridin-2-yl)-1H-benzo[d]iMidazole-5-carboxaMido)propanoate acetate Ethyl 3-(2-(((4-carbaMiMidoylphenyl)aMino)Methyl)-1-Methyl-N-(pyridin-2-yl)-1H-benzo[d]iMidazole-5-carboxaMido)propanoate acetate 1188263-64-0 C29H33N7O4
Methyl azepane-4-carboxylate hydrochloride Methyl azepane-4-carboxylate hydrochloride 1383132-15-7 C8H16ClNO2
(3R,5S)-5-Methylpyrrolidin-3-ol (3R,5S)-5-Methylpyrrolidin-3-ol 1108234-23-6 C5H11NO
2-Butyl-2,3-dihydrothieno[3,4-b]-1,4-dioxine 2-Butyl-2,3-dihydrothieno[3,4-b]-1,4-dioxine 552857-06-4 C10H14O2S
(S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile (S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile 1448440-39-8 C7H9F2N3O
5,6,7,8-Tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid ethyl ester 5,6,7,8-Tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid ethyl ester 951627-01-3 C9H13N3O2
Isopropyl 1H-imidazole-1-carboxylate Isopropyl 1H-imidazole-1-carboxylate 82998-18-3 C7H10N2O2
Di-Fluoro ethylene carbonate Di-Fluoro ethylene carbonate 311810-76-1 C3H2F2O3
AKOS B019512 AKOS B019512 5775-82-6 C5H7BrN2
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