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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
(1S,3S)-phenylethylpyrrolidinylMethanol (1S,3S)-phenylethylpyrrolidinylMethanol 173724-95-3 C13H19NO
6-benzyl-2,4-dichloro-8,8-difluoro-5,6,7,8-tetrahydropyrido[4,3-d]pyriMidine HYDROCHLORIDE 6-benzyl-2,4-dichloro-8,8-difluoro-5,6,7,8-tetrahydropyrido[4,3-d]pyriMidine HYDROCHLORIDE 1864059-82-4 C14H12Cl3F2N3
(5S)-5-Methyl-2-Pyrrolidinone (5S)-5-Methyl-2-Pyrrolidinone 1558-60-7 C5H9NO
(3S,5S)-5-Methylpyrrolidin-3-ol (3S,5S)-5-Methylpyrrolidin-3-ol 1108234-24-7 C5H11NO
IMidazo[1,2-d][1,4]benzoxazepine, 9-broMo-5,6-dihydro-2-[3-Methyl-1-(1-Methylethyl)-1H-1,2,4-triazol-5-yl]- IMidazo[1,2-d][1,4]benzoxazepine, 9-broMo-5,6-dihydro-2-[3-Methyl-1-(1-Methylethyl)-1H-1,2,4-triazol-5-yl]- 1282514-63-9 C17H18BrN5O
(S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile 2,2,2-trifluoroacetate (S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile 2,2,2-trifluoroacetate 1448440-40-1 C9H10F5N3O3
2-Pyrrolidinecarboxamide, N-(4-phenyl-1,2,3-thiadiazol-5-yl)-, monohydrochloride, (2S)- (9CI) 2-Pyrrolidinecarboxamide, N-(4-phenyl-1,2,3-thiadiazol-5-yl)-, monohydrochloride, (2S)- (9CI) 873581-19-2 C13H15ClN4OS
7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2,4-diol 7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2,4-diol 1478126-83-8 C7H8N2O3
3-Oxazolidinecarboxylic acid, 4-methyl-2,5-dioxo-, 1,1-dimethylethyl ester, (4R)- 3-Oxazolidinecarboxylic acid, 4-methyl-2,5-dioxo-, 1,1-dimethylethyl ester, (4R)- 161422-40-8 C9H13NO5
(1H-Imidazol-2-yl)-hydrazine hydrochloride (1H-Imidazol-2-yl)-hydrazine hydrochloride 1187929-07-2 C3H7ClN4
P4S10-Pyridine complex P4S10-Pyridine complex 16610-51-8 C10H10N2P2S5
1,1'-Thiocarbonyldiimidazole 1,1'-Thiocarbonyldiimidazole 6160-65-2 C7H6N4S
(2R,3R)-2-PHENYL-PYRROLIDINE-3-CARBOXYLIC ACID (2R,3R)-2-PHENYL-PYRROLIDINE-3-CARBOXYLIC ACID 1241684-18-3 C11H13NO2
(R)-3-Methylpiperazin-2-one (R)-3-Methylpiperazin-2-one 922178-61-8 C5H10N2O
3-CYCLOHEXYL-PYRROLIDINE 3-CYCLOHEXYL-PYRROLIDINE 78813-85-1 C10H19N
Vinyl pyridine Vinyl pyridine C7H7N
2-Morpholinoethanol 2-Morpholinoethanol 622-40-2 C6H13NO2
8-Ethyl-2-methanethio-8H-pyrido[2,3-d]pyrimidin-7-one 8-Ethyl-2-methanethio-8H-pyrido[2,3-d]pyrimidin-7-one 211244-82-5 C10H11N3OS
methyl 5-methoxy-3H-benzo[d]imidazole-4-carboxylate methyl 5-methoxy-3H-benzo[d]imidazole-4-carboxylate 1193789-02-4 C10H10N2O3
3-Bromo-2-chloro-4-(trifluoromethyl)pyridine 3-Bromo-2-chloro-4-(trifluoromethyl)pyridine 1211588-39-4 C6H2BrClF3N
3-Fluoro-2-Bromo-4-(trifluoromethyl)pyridine 3-Fluoro-2-Bromo-4-(trifluoromethyl)pyridine 1227577-05-0 C6H2BrF4N
Cetilistat Impurity 1 Cetilistat Impurity 1 282526-87-8 C21H31NO3
Cytidine, 4'-C-(chloromethyl)-2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-2'-fluoro- Cytidine, 4'-C-(chloromethyl)-2'-deoxy-3'-O-[(1,1-dimethylethyl)dimethylsilyl]-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-2'-fluoro- 1445379-90-7 C32H45ClFN3O4Si2
Benzamide, N-[2-[(3S)-3-[[cis-4-hydroxy-4-[5-(2-pyrimidinyl)-2-pyridinyl]cyclohexyl]amino]-1-pyrrolidinyl]-2-oxoethyl]-3-(trifluoromethyl)- Benzamide, N-[2-[(3S)-3-[[cis-4-hydroxy-4-[5-(2-pyrimidinyl)-2-pyridinyl]cyclohexyl]amino]-1-pyrrolidinyl]-2-oxoethyl]-3-(trifluoromethyl)- 1372407-07-2 C29H31F3N6O3
ETHYL 6-FLUORO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLATE ETHYL 6-FLUORO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLATE 367500-93-4 C10H9FN2O2
5-BROMO-1H-BENZOTRIAZOLE 5-BROMO-1H-BENZOTRIAZOLE 32046-62-1 C6H4BrN3
5-BROMO-7-INDAZOLECARBOXYLIC ACID METHYL ESTER 5-BROMO-7-INDAZOLECARBOXYLIC ACID METHYL ESTER 898747-24-5 C9H7BrN2O2
8-Methyl-[1,2,4]triazolo[4,3-a]pyridine 8-Methyl-[1,2,4]triazolo[4,3-a]pyridine 4997-81-3 C7H7N3
MD-PHP MD-PHP 776994-64-0 C17H23NO3
4,4'-(1,4-phenylene)bis(4H-1,2,4-triazole) 4,4'-(1,4-phenylene)bis(4H-1,2,4-triazole) 681004-60-4 C10H8N6
4-chloro-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine 4-chloro-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine 1203566-02-2 C13H18ClIN2OSi
Chloro[1,3-bis(t-butyl)-2H-imidazol-2-ylidene]gold(I) Chloro[1,3-bis(t-butyl)-2H-imidazol-2-ylidene]gold(I) 839722-07-5 C11H20AuClN2
6-oxo-1,6-dihydropyridine-3-sulfonyl chloride 6-oxo-1,6-dihydropyridine-3-sulfonyl chloride 1357566-60-9 C5H4ClNO3S
2-((5-bromopyrimidin-2-yl)oxy)ethan-1-ol 2-((5-bromopyrimidin-2-yl)oxy)ethan-1-ol 1246922-88-2 C6H7BrN2O2
5,7-DIBROMO-1H-PYRAZOLO[4,3-B]PYRIDINE 5,7-DIBROMO-1H-PYRAZOLO[4,3-B]PYRIDINE 1956379-02-4 C6H3Br2N3
2-(Cyanomethyl)benzimidazole 2-(Cyanomethyl)benzimidazole 4414-88-4 C9H7N3
5-fluoro-1H-pyrimidine-2,4-dione 5-fluoro-1H-pyrimidine-2,4-dione 1189423-58-2 C4H3FN2O2
Oxymetazoline Oxymetazoline 1491-59-4 C16H24N2O
3-BROMO-6-METHYLIMIDAZO[1,2-A]PYRIDINE 3-BROMO-6-METHYLIMIDAZO[1,2-A]PYRIDINE 866135-71-9 C8H7BrN2
1-(2-aminoethyl)-5-[(4-chlorophenyl)methyl]-1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one 1-(2-aminoethyl)-5-[(4-chlorophenyl)methyl]-1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one 1105196-80-2 C14H14ClN5O
3-(5-PIPERIDIN-4-YL-1,2,4-OXADIAZOL-3-YL)PYRIDINE 3-(5-PIPERIDIN-4-YL-1,2,4-OXADIAZOL-3-YL)PYRIDINE 114474-26-9 C9H7N3O2
2,2,6-Trimethyl-4H-1,3-dioxin-4-one 2,2,6-Trimethyl-4H-1,3-dioxin-4-one 5394-63-8 C7H10O3
4-Bromo-1-chloro-2-nitrobenzene 4-Bromo-1-chloro-2-nitrobenzene 16588-24-2 C6H3BrClNO2
1,5-DIMETHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE 1,5-DIMETHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE 79080-31-2 C6H7F3N2
4-(BROMOMETHYL)ISOXAZOLE 4-(BROMOMETHYL)ISOXAZOLE 6455-40-9 C4H4BrNO
4-chloro-7-(2-methoxyethoxy)quinazoline 4-chloro-7-(2-methoxyethoxy)quinazoline 199327-54-3 C11H11ClN2O2
Ethyl 4-iodo-1H-imidazole-2-carboxylate Ethyl 4-iodo-1H-imidazole-2-carboxylate 1824103-80-1 C6H7IN2O2
4-(2-THIAZOLYL)PHENOL 4-(2-THIAZOLYL)PHENOL 81015-49-8 C9H7NOS
7-chloro-3H,4H-thieno[3,4-d]pyrimidin-4-one 7-chloro-3H,4H-thieno[3,4-d]pyrimidin-4-one 53826-83-8 C6H3ClN2OS
5-AMINO-1,3-DIMETHYL-1H-PYRAZOLE-4-CARBONITRILE 5-AMINO-1,3-DIMETHYL-1H-PYRAZOLE-4-CARBONITRILE 54820-92-7 C6H8N4
(R)-3-Fluoropyrrolidine-1-sulfonyl chloride (R)-3-Fluoropyrrolidine-1-sulfonyl chloride 1411774-27-0 C4H7ClFNO2S
(S)-Ethyl 6-(5-bromofuran-2-yl)-7,9-dimethyl-8,10-dioxo-11-phenyl-7,8,9,10-tetrahydro-6H-benzo[b]pyrimido[4',5':3,4]pyrrolo[1,2-d][1,4]oxazine-2-carboxylate (S)-Ethyl 6-(5-bromofuran-2-yl)-7,9-dimethyl-8,10-dioxo-11-phenyl-7,8,9,10-tetrahydro-6H-benzo[b]pyrimido[4',5':3,4]pyrrolo[1,2-d][1,4]oxazine-2-carboxylate 1415390-49-6 C28H22BrN3O6
(3S,4R)-3-amino-4-hydroxypyrrolidin-2-one hydrochloride (3S,4R)-3-amino-4-hydroxypyrrolidin-2-one hydrochloride 2446872-13-3 C4H9ClN2O2
(5S)-2 2 3-TRIMETHYL-5-PHENYLMETHYL-4-I& (5S)-2 2 3-TRIMETHYL-5-PHENYLMETHYL-4-I& 278173-23-2 C13H18N2O.ClH
3-TERT-BUTYLISOXAZOL-5-AMINE 3-TERT-BUTYLISOXAZOL-5-AMINE 59669-59-9 C7H12N2O
(S)-BAY 73-6691 (S)-BAY 73-6691 794568-91-5 C15H12ClF3N4O
2,6-bis[1,1-bis(pyridin-2-yl)ethyl]pyridine 2,6-bis[1,1-bis(pyridin-2-yl)ethyl]pyridine 105631-67-2 C29H25N5
3-chloroimidazo[1,2-a]pyridine-6-sulfonyl chloride 3-chloroimidazo[1,2-a]pyridine-6-sulfonyl chloride 2306270-26-6 C7H4Cl2N2O2S
Dodecanedioic acid, 1,12-bis(2,5-dioxo-1-pyrrolidinyl) ester Dodecanedioic acid, 1,12-bis(2,5-dioxo-1-pyrrolidinyl) ester 75472-90-1 C20H28N2O8
1,4-Di(pyridin-2-yl)benzene 1,4-Di(pyridin-2-yl)benzene 57477-09-5 C16H12N2
7-chloronaphtho[1,2-b]benzofuran 7-chloronaphtho[1,2-b]benzofuran 2411141-56-3 C16H9ClO
7-Chloro-5-(chloromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine 7-Chloro-5-(chloromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine 63882-72-4 C6H4Cl2N4
5-((Benzyloxy)carbonyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid 5-((Benzyloxy)carbonyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid 100307-49-1 C15H15N3O4
2-(Chloromethyl)thieno[3,2-d]pyrimidine 2-(Chloromethyl)thieno[3,2-d]pyrimidine 77294-17-8 C7H5ClN2S
5-Bromo-[1,2,4]triazolo[1,5-a]pyrimidine 5-Bromo-[1,2,4]triazolo[1,5-a]pyrimidine 154695-81-5 C5H3BrN4
6-Methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde 6-Methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde 1263059-02-4 C8H7N3O
(R)-(5-oxopyrrolidin-2-yl)methyl methanesulfonate (R)-(5-oxopyrrolidin-2-yl)methyl methanesulfonate 128811-47-2 C6H11NO4S
(S)-3-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol (S)-3-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol 1163680-85-0 C6H7N3O4
6,6-Dimethyl-6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione 6,6-Dimethyl-6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione 67566-51-2 C9H12N2O2
1,3-Diphenyl-3-imidazo[4,5-b]pyrazinium Iodide 1,3-Diphenyl-3-imidazo[4,5-b]pyrazinium Iodide 1311465-22-1 C17H13IN4
2,3-DIHYDRO-2-METHYLBENZOFURAN 2,3-DIHYDRO-2-METHYLBENZOFURAN 1746-11-8 C9H10O
4-CHLORO-2-METHOXY-PYRIDINE 4-CHLORO-2-METHOXY-PYRIDINE 72141-44-7 C6H6ClNO
3,5-DIBROMO-2-METHYLTHIOPHENE 3,5-DIBROMO-2-METHYLTHIOPHENE 29421-73-6 C5H4Br2S
7-METHYL-2-PHENYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID 7-METHYL-2-PHENYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID 220465-49-6 C15H12N2O2
2-NITROFURAN 2-NITROFURAN 609-39-2 C4H3NO3
N-Boc-2-piperidone N-Boc-2-piperidone 85908-96-9 C10H17NO3
5-CHLORO-2-BENZOTHIAZOLINONE 5-CHLORO-2-BENZOTHIAZOLINONE 20600-44-6 C7H4ClNOS
4-NITRO-1H-IMIDAZOLE-5-CARBOXYLIC ACID 4-NITRO-1H-IMIDAZOLE-5-CARBOXYLIC ACID 40507-59-3 C4H3N3O4
Tetrahydrofuran-3-yl)methanamine Tetrahydrofuran-3-yl)methanamine 165253-31-6 C5H11NO
(R,R)-2,2'-(DIMETHYLMETHYLENE)BIS(4-PHENYL-2-OXAZOLINE) (R,R)-2,2'-(DIMETHYLMETHYLENE)BIS(4-PHENYL-2-OXAZOLINE) 150529-93-4 C21H22N2O2
4-MORPHOLINECARBONITRILE 4-MORPHOLINECARBONITRILE 1530-89-8 C5H8N2O
(R)-4-ISOBUTYL-OXAZOLIDINE-2,5-DIONE (R)-4-ISOBUTYL-OXAZOLIDINE-2,5-DIONE 51018-87-2 C7H11NO3
ETHYL 2-AMINO-1-METHYLIMIDAZOLE-5-CARBOXYLATE HYDROCHLORIDE ETHYL 2-AMINO-1-METHYLIMIDAZOLE-5-CARBOXYLATE HYDROCHLORIDE 39070-12-7 C7H12ClN3O2
4-(4-METHOXY-PHENYL)-1,2,3,6-TETRAHYDRO-PYRIDINE 4-(4-METHOXY-PHENYL)-1,2,3,6-TETRAHYDRO-PYRIDINE 59954-73-3 C12H15NO
1H-Imidazole-1-carboxylic acid, 1-(9,10-dihydro-9,10-dioxo-2-anthracenyl)ethyl ester 1H-Imidazole-1-carboxylic acid, 1-(9,10-dihydro-9,10-dioxo-2-anthracenyl)ethyl ester 1418139-51-1 C20H14N2O4
ETHYL 5-AMINO-1-BENZYLIMIDAZOLE-4-CARBOXYLATE ETHYL 5-AMINO-1-BENZYLIMIDAZOLE-4-CARBOXYLATE 68462-61-3 C13H15N3O2
1,3-Benzenedicarboxylic acid, 5-(1H-imidazol-1-ylmethyl)- 1,3-Benzenedicarboxylic acid, 5-(1H-imidazol-1-ylmethyl)- 1393930-96-5 C12H10N2O4
2,4-di(pyridin-2-yl)-6-(pyridin-4-yl)pyrimidine 2,4-di(pyridin-2-yl)-6-(pyridin-4-yl)pyrimidine 2412116-11-9 C19H13N5
5-Pyrimidinemethanamine, N-(1-ethyl-1H-pyrazol-4-yl)- 5-Pyrimidinemethanamine, N-(1-ethyl-1H-pyrazol-4-yl)- 1339090-16-2 C10H13N5
5H-Pyrrolo[3,2-d]pyrimidine-5-carboxylic acid, 2-chloro-, 1,1-dimethylethyl ester 5H-Pyrrolo[3,2-d]pyrimidine-5-carboxylic acid, 2-chloro-, 1,1-dimethylethyl ester 1936241-06-3 C11H12ClN3O2
2H-Benzimidazol-2-one, 5-amino-1,3-dihydro-1,3-dimethyl-6-(3-propoxyphenoxy)- 2H-Benzimidazol-2-one, 5-amino-1,3-dihydro-1,3-dimethyl-6-(3-propoxyphenoxy)- 1800477-35-3 C18H21N3O3
1-(3,5-bis(trifluoromethyl)phenyl)-1H-imidazole 1-(3,5-bis(trifluoromethyl)phenyl)-1H-imidazole 1088567-34-3 C11H6F6N2
4-CHLORO-1,6-DIMETHYL-1H-IMIDAZO[4,5-C]PYRIDINE 4-CHLORO-1,6-DIMETHYL-1H-IMIDAZO[4,5-C]PYRIDINE 870135-17-4 C8H8ClN3
Temoporfin Temoporfin 122341-38-2 C44H32N4O4
4-(Methylamino)phenol 4-(Methylamino)phenol 150-75-4 C7H9NO
Etozolin Etozolin 73-09-6 C13H20N2O3S
1-allyl-2-methyl-5-nitro-1H-imidazole 1-allyl-2-methyl-5-nitro-1H-imidazole 13230-43-8 C7H9N3O2
2,5-Oxazolidinedione, 4-[[4-(acetyloxy)phenyl]methyl]-, (4S)- 2,5-Oxazolidinedione, 4-[[4-(acetyloxy)phenyl]methyl]-, (4S)- 23224-65-9 C12H11NO5
1,3-dimethylpyrrolidine-2,5-dione 1,3-dimethylpyrrolidine-2,5-dione 15542-96-8 C6H9NO2
1,3-dihydro-1-[1-benzyl-4-piperidinyl]-2H-benzimidazol-2-one 1,3-dihydro-1-[1-benzyl-4-piperidinyl]-2H-benzimidazol-2-one 16148-06-4 C19H21N3O
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