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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
2H-Benzimidazol-2-one,1,3-dihydro-4-methoxy-(9CI) 2H-Benzimidazol-2-one,1,3-dihydro-4-methoxy-(9CI) 69053-51-6 C8H8N2O2
5-bromo-1-methyl-1,2,4-triazole 5-bromo-1-methyl-1,2,4-triazole 16681-72-4 C3H4BrN3
3,5-Dibromo-2-hydroxy-4-methylpyridine 3,5-Dibromo-2-hydroxy-4-methylpyridine 89581-53-3 C6H5Br2NO
Imidazo[1,2-a]pyridine, HCl Imidazo[1,2-a]pyridine, HCl 34167-64-1 C7H7ClN2
5-NITROTHIOPHENE-2-CARBOXYLICMETHYLESTER 5-NITROTHIOPHENE-2-CARBOXYLICMETHYLESTER 5832-01-9 C6H5NO4S
2-Chloro-4-methylquinazoline 2-Chloro-4-methylquinazoline 6141-14-6 C9H7ClN2
H-Lys-Pro-AMC H-Lys-Pro-AMC 133066-53-2 C21H28N4O4
5,7-DICHLORO-2-METHYL-[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE 5,7-DICHLORO-2-METHYL-[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE 1373519-64-2 C6H4Cl2N4
5-BROMOIMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 5-BROMOIMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 1026201-52-4 C8H5BrN2O2
6-BROMO[1,2,4]TRIAZOLO[4,3-A]PYRIMIDINE 6-BROMO[1,2,4]TRIAZOLO[4,3-A]PYRIMIDINE 1019023-12-1 C5H3BrN4
7-CHLORO[1,2,4]TRIAZOLO[1,5-C]PYRIMIDINE 7-CHLORO[1,2,4]TRIAZOLO[1,5-C]PYRIMIDINE 1159811-23-0 C5H3ClN4
1-P-TOLYLPYRAZOLE 1-P-TOLYLPYRAZOLE 20518-17-6 C10H10N2
1-[2-(3-BROMOPHENOXY)ETHYL]-PYRROLIDINE 1-[2-(3-BROMOPHENOXY)ETHYL]-PYRROLIDINE 23136-18-7 C12H16BrNO
5-chloro-7-methyl-1H-pyrrolo[3,2-b]pyridine 5-chloro-7-methyl-1H-pyrrolo[3,2-b]pyridine 357263-43-5 C8H7ClN2
PYRIDO[3,4-D]PYRIMIDINE-2,4(1H,3H)-DIONE PYRIDO[3,4-D]PYRIMIDINE-2,4(1H,3H)-DIONE 21038-67-5 C7H5N3O2
1-[4-(BROMOMETHYL)PHENYL]-1H-PYRAZOLE 1-[4-(BROMOMETHYL)PHENYL]-1H-PYRAZOLE 368869-85-6 C10H9BrN2
2-(ETHYLTHIO)-2-IMIDAZOLINE 2-(ETHYLTHIO)-2-IMIDAZOLINE 7320-60-7 C5H10N2S
5-bromooxazole 5-bromooxazole 1060812-80-7 C3H2BrNO
1-(2-fluorobenzyl)-5-oxopyrrolidine-3-carboxylic acid(SALTDATA: FREE) 1-(2-fluorobenzyl)-5-oxopyrrolidine-3-carboxylic acid(SALTDATA: FREE) 845546-24-9 C12H12FNO3
1-(3-aminopropyl)-2,5-pyrrolidinedione(SALTDATA: HCl) 1-(3-aminopropyl)-2,5-pyrrolidinedione(SALTDATA: HCl) 54052-99-2 C7H12N2O2
1-benzyl-5-bromo-1H-imidazole 1-benzyl-5-bromo-1H-imidazole 132430-59-2 C10H9BrN2
2,4,5-triMethyl-4,5-dihydro-1H-iMidazole-4,5-diol 2,4,5-triMethyl-4,5-dihydro-1H-iMidazole-4,5-diol 740025-56-3 C6H12N2O2
7-BroMo-3-MethyliMidazo[1,5-a]pyridine 7-BroMo-3-MethyliMidazo[1,5-a]pyridine 1379355-19-7 C8H7BrN2
1H-Pyrazolo[3,4-d]pyrimidine-4-carboxylic acid 1H-Pyrazolo[3,4-d]pyrimidine-4-carboxylic acid 1095822-28-8 C6H4N4O2
Pyridine, 4-[2-(1H-iMidazol-2-yl)phenyl]- Pyridine, 4-[2-(1H-iMidazol-2-yl)phenyl]- 608515-26-0 C14H11N3
1-(2-HydroxyMethyl-pyrrolidin-1-yl)-ethanone 1-(2-HydroxyMethyl-pyrrolidin-1-yl)-ethanone 27822-68-0 C7H13NO2
1-Acetyl-pyrrolidin-3-one 1-Acetyl-pyrrolidin-3-one 34086-58-3 C6H9NO2
1-tert-butyl-5-phenyl-1H-pyrazole 1-tert-butyl-5-phenyl-1H-pyrazole 1204355-48-5 C13H16N2
4-broMo-1-Methyl-1H-pyrazolo[3,4-c]pyridine 4-broMo-1-Methyl-1H-pyrazolo[3,4-c]pyridine 1032943-41-1 C7H6BrN3
4H-IMidazo[4,5-c]pyridin-4-one, 7-broMo-1,5-dihydro- 4H-IMidazo[4,5-c]pyridin-4-one, 7-broMo-1,5-dihydro- 163452-70-8 C6H4BrN3O
IMidazo[1,2-a]pyridin-6-aMine, 2-Methyl- IMidazo[1,2-a]pyridin-6-aMine, 2-Methyl- 860258-05-5 C8H9N3
7-chloro-5-(Methylthio)iMidazo[1,2-c]pyriMidine 7-chloro-5-(Methylthio)iMidazo[1,2-c]pyriMidine 872059-27-3 C7H6ClN3S
2-(chloroMethyl)-6-(trifluoroMethyl)pyridine 2-(chloroMethyl)-6-(trifluoroMethyl)pyridine 849094-03-7 C7H5ClF3N
tert-Butyl ((1H-benzo[d]imidazol-2-yl)methyl)carbamate tert-Butyl ((1H-benzo[d]imidazol-2-yl)methyl)carbamate 189560-83-6 C13H17N3O2
6-fluoro-3-(4-(3-Methoxy-4-(4-Methyl-1H-iMidazol-1-yl)phenyl)-1H-1,2,3-triazol-1-yl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one 6-fluoro-3-(4-(3-Methoxy-4-(4-Methyl-1H-iMidazol-1-yl)phenyl)-1H-1,2,3-triazol-1-yl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one 1093978-67-6 C23H21FN6O2
1,2-Pyrrolidinedicarboxylic acid, 5-hydroxy-, 1-(1,1-diMethylethyl) 2-Methyl ester, (2S)- 1,2-Pyrrolidinedicarboxylic acid, 5-hydroxy-, 1-(1,1-diMethylethyl) 2-Methyl ester, (2S)- 188200-05-7 C11H19NO5
4-PyriMidinecarboxylic acid, 6-aMino-5-chloro-, ethyl ester 4-PyriMidinecarboxylic acid, 6-aMino-5-chloro-, ethyl ester 1097250-86-6 C7H8ClN3O2
2-Chloro-1H-imidazole 2-Chloro-1H-imidazole 16265-04-6 C3H3ClN2
1-(Piperidin-4-yl)pyrrolidin-2-one HCl 1-(Piperidin-4-yl)pyrrolidin-2-one HCl 548769-02-4 C9H17ClN2O
3-BroMo-4-nitropyrazole 3-BroMo-4-nitropyrazole 784193-37-9 C3H2BrN3O2
5-Methoxy-pyridine-2-sulfonyl chloride 5-Methoxy-pyridine-2-sulfonyl chloride 1060801-83-3 C6H6ClNO3S
Pyrido[4,3-d]pyriMidine-2,4(1H,3H)-dione Pyrido[4,3-d]pyriMidine-2,4(1H,3H)-dione 16952-65-1 C7H5N3O2
ethyl 5-aMino-2-chloropyriMidine-4-carboxylate ethyl 5-aMino-2-chloropyriMidine-4-carboxylate 59950-50-4 C7H8ClN3O2
1-(CyclopropylMethyl)pyrazole 1-(CyclopropylMethyl)pyrazole 1344382-51-9 C7H10N2
Bromazolam Bromazolam 71368-80-4 C17H13BrN4
4,5-dibroMo-1-Methyl-1H-1,2,3-triazole 4,5-dibroMo-1-Methyl-1H-1,2,3-triazole 25537-64-8 C3H3Br2N3
5-BroMo-4-chloronicotinonitrile 5-BroMo-4-chloronicotinonitrile 1160923-98-7 C6H2BrClN2
Spiro[pyrrolidine-2,7'(6'H)-[2H]pyrrolo[2,1-b][1,3]thiazine]-1,4'-dicarboxylic acid, tetrahydro-6'-oxo-, 1-(1,1-diMethylethyl) 4'-Methyl ester, (2R,4'R,8'aR)- Spiro[pyrrolidine-2,7'(6'H)-[2H]pyrrolo[2,1-b][1,3]thiazine]-1,4'-dicarboxylic acid, tetrahydro-6'-oxo-, 1-(1,1-diMethylethyl) 4'-Methyl ester, (2R,4'R,8'aR)- 221040-37-5 C17H26N2O5S
Senexin A Senexin A 1366002-50-7 C17H14N4
di-tert-butyl (4-chloropyriMidin-2-yl)carbaMate di-tert-butyl (4-chloropyriMidin-2-yl)carbaMate 1464788-84-8 C14H20ClN3O4
7-Bromo-2-methylimidazo[1,2-a]-pyridine-3-carboxylic acid 7-Bromo-2-methylimidazo[1,2-a]-pyridine-3-carboxylic acid 1159831-07-8 C9H7BrN2O2
1-Hydroxy-1,3-dihydro-2,1-benzoxaborole-6-carboxylic acid 1-Hydroxy-1,3-dihydro-2,1-benzoxaborole-6-carboxylic acid 1221343-14-1 C8H7BO4
2,4-dichloro-5,7-dihydrothieno[3,4-d]pyriMidine 2,4-dichloro-5,7-dihydrothieno[3,4-d]pyriMidine 74901-71-6 C6H4Cl2N2S
6-BroMo-iMidazo[1,2-a]pyriMidine-2-carboxylic acid 6-BroMo-iMidazo[1,2-a]pyriMidine-2-carboxylic acid 907945-69-1 C7H4BrN3O2
FMoc-α-Me-D-Pro-OH FMoc-α-Me-D-Pro-OH 1286768-33-9 C21H21NO4
2-CHLORO-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID 2-CHLORO-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID 522604-25-7 C8H5ClN2O2
BOC-3-FLUORO-4-OXOPYRROLIDINE BOC-3-FLUORO-4-OXOPYRROLIDINE 845894-03-3 C9H14FNO3
3-ETHYL-4-IODO-1H-PYRAZOLE 3-ETHYL-4-IODO-1H-PYRAZOLE 442876-19-9 C5H7IN2
1-[2-(azetidin-1-yl)ethyl]-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 1-[2-(azetidin-1-yl)ethyl]-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 1422126-12-2 C14H24BN3O2
7-Chloro-6-iodoimidazo[1,2-a]pyrimidin-5(1H)-one 7-Chloro-6-iodoimidazo[1,2-a]pyrimidin-5(1H)-one 1799434-64-2 C6H3ClIN3O
1-isopropylpyrimidine-2,4,6(1H,3H,5H)-trione 1-isopropylpyrimidine-2,4,6(1H,3H,5H)-trione 69998-14-7 C7H10N2O3
6-(3-methoxyphenyl)imidazo[2,1-b]thiazole 6-(3-methoxyphenyl)imidazo[2,1-b]thiazole 92754-06-8 C12H10N2OS
7-benzenesulfonyl-4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 7-benzenesulfonyl-4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 208459-84-1 C12H7ClIN3O2S
2-(4-(2H-tetrazol-5-yl)phenoxy)-5-chloro-3-fluoropyridine 2-(4-(2H-tetrazol-5-yl)phenoxy)-5-chloro-3-fluoropyridine 1799681-96-1 C12H7ClFN5O
1-Methylpyrrolidin-3-amine hydrochloride 1-Methylpyrrolidin-3-amine hydrochloride 1538307-77-5 C5H13ClN2
7-(4-Methoxybenzyl)-5-Methyl-3-(Phenylamino)-2H-Pyrazolo[3,4-D]Pyrimidine-4,6(5H,7H)-Dione 7-(4-Methoxybenzyl)-5-Methyl-3-(Phenylamino)-2H-Pyrazolo[3,4-D]Pyrimidine-4,6(5H,7H)-Dione 1160521-51-6 C20H19N5O3
3,3'-Methylenebis(1-tert-butyl-3-imidazolium Bromide) 3,3'-Methylenebis(1-tert-butyl-3-imidazolium Bromide) 247902-48-3 C15H26Br2N4
6-Methylimidazo[1,2-a]pyrimidine-3-carboxylic acid 6-Methylimidazo[1,2-a]pyrimidine-3-carboxylic acid 1020035-04-4 C8H7N3O2
1-(2-Methoxyethyl)-1-methylpyrrolidinium Bis(fluorosulfonyl)imide 1-(2-Methoxyethyl)-1-methylpyrrolidinium Bis(fluorosulfonyl)imide 1235234-47-5 C8H18F2N2O5S2
1-Methylimidazole 1-Methylimidazole 616-47-7 C4H6N2
2-Cyclopropyl-4-iodo-1-isopropyl-1H-imidazole 2-Cyclopropyl-4-iodo-1-isopropyl-1H-imidazole 824431-88-1 C9H13IN2
tert-butyl 3-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]pyrrolidine-1-carboxylate tert-butyl 3-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]pyrrolidine-1-carboxylate 1359974-18-7 C18H30BN3O4
4-CHLORO-6,7-DIETHOXY-QUINAZOLINE 4-CHLORO-6,7-DIETHOXY-QUINAZOLINE 162363-46-4 C12H13ClN2O2
trans-4-fluoro-3-hydroxypyrrolidine hydrochloride trans-4-fluoro-3-hydroxypyrrolidine hydrochloride 2006333-41-9 C4H9ClFNO
9,9'-Bis([1,1'-biphenyl]-3-yl)-3,3'-bi-9H-carbazole 9,9'-Bis([1,1'-biphenyl]-3-yl)-3,3'-bi-9H-carbazole 1352040-89-1 C48H32N2
7-Bromo-2,4-dichloropyrido[3,2-d]pyrimidine 7-Bromo-2,4-dichloropyrido[3,2-d]pyrimidine 1215074-41-1 C7H2BrCl2N3
Chloro[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]gold(I) Chloro[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]gold(I) 852445-82-0 C21H26AuClN2
4-Bromo-1,2-dimethyl-1H-benzo[d]imidazole 4-Bromo-1,2-dimethyl-1H-benzo[d]imidazole 1379361-12-2 C9H9BrN2
6-BROMO-2-CHLOROOXAZOLO[5,4-B]PYRIDINE 6-BROMO-2-CHLOROOXAZOLO[5,4-B]PYRIDINE 1782797-89-0 C6H2BrClN2O
1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-2-one 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-2-one 1003309-09-8 C16H22BNO3
2-(1H-Pyrazol-1-yl)-5-(trifluoromethyl)pyrimidine 2-(1H-Pyrazol-1-yl)-5-(trifluoromethyl)pyrimidine 1398504-38-5 C8H5F3N4
FHMKYTDEGLFVSL-UHFFFAOYSA-N FHMKYTDEGLFVSL-UHFFFAOYSA-N 76182-29-1 C6H7ClN2O2
(S)-Pyrrolidine-2-carbonitrile hydrochloride (S)-Pyrrolidine-2-carbonitrile hydrochloride 65732-69-6 C5H9ClN2
8-bromo-2-chloroimidazo[1,2-a]pyridine 8-bromo-2-chloroimidazo[1,2-a]pyridine 1260902-12-2 C7H4BrClN2
4-HYDROXYMETHYL-5-METHYLIMIDAZOLE 4-HYDROXYMETHYL-5-METHYLIMIDAZOLE 29636-87-1 C5H8N2O
CHEMBRDG-BB 4010221 CHEMBRDG-BB 4010221 6857-34-7 C9H8N2S
N-CYANOACETYLPYRROLIDINE N-CYANOACETYLPYRROLIDINE 14227-95-3 C7H10N2O
1-Methylindole 1-Methylindole 603-76-9 C9H9N
4-(MORPHOLINOMETHYL)BENZYLAMINE 4-(MORPHOLINOMETHYL)BENZYLAMINE 91271-84-0 C12H18N2O
5-Chloro-1-(4-piperidyl)-2-benzimidazolinone 5-Chloro-1-(4-piperidyl)-2-benzimidazolinone 53786-28-0 C12H14ClN3O
(6-Methyl-thieno[2,3-d]pyrimidin-4-yl)-hydrazine (6-Methyl-thieno[2,3-d]pyrimidin-4-yl)-hydrazine 439692-69-0 C7H8N4S
3-Indoleacetonitrile 3-Indoleacetonitrile 771-51-7 C10H8N2
4-(FMOC-AMINO)-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLIC ACID 4-(FMOC-AMINO)-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLIC ACID 252206-28-3 C20H17N3O4
2-Methylene-1,3-dioxepane 2-Methylene-1,3-dioxepane 69814-56-8 C6H10O2
5,5',5'',5'''-([2,2'-bi(1,3-dithiolylidene)]-4,4',5,5'-tetrayl)tetraisophthalic acid 5,5',5'',5'''-([2,2'-bi(1,3-dithiolylidene)]-4,4',5,5'-tetrayl)tetraisophthalic acid 2172997-02-1 C38H20O16S4
6-Methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol 6-Methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol 2222660-14-0 C7H9N3O4
5-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole 5-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole 34605-70-4 C10H13N3
7H-pyrrolo[2,3-d]pyrimidine-2-carboxylic acid 7H-pyrrolo[2,3-d]pyrimidine-2-carboxylic acid 1314723-98-2 C7H5N3O2
10H-spiro[acridine-9,9'-xanthene] 10H-spiro[acridine-9,9'-xanthene] 1443130-79-7 C25H17NO
(S)-1-(2-(trifluoromethyl)pyrimidin-5-yl)ethan-1-amine (S)-1-(2-(trifluoromethyl)pyrimidin-5-yl)ethan-1-amine 1948237-00-0 C7H8F3N3
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