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
3,5-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
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
2-Amino-3,5-dinitrothiophene 2-Amino-3,5-dinitrothiophene 2045-70-7 C4H3N3O4S
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
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
2,5-dimethylpyrrolidine-1-propanol 2,5-dimethylpyrrolidine-1-propanol 1904-16-1 C9H19NO
2-(2-phenylethyl)pyridine 2-(2-phenylethyl)pyridine 2116-62-3 C13H13N
1-(4-methylpyrimidin-2-yl)ethan-1-one 1-(4-methylpyrimidin-2-yl)ethan-1-one 71850-85-6 C7H8N2O
(R)-3-(pyrrolidin-2-yl)pyridine (R)-3-(pyrrolidin-2-yl)pyridine 7076-23-5 C9H12N2
2-azido-1H-benzimidazole 2-azido-1H-benzimidazole 1516-74-1 C7H5N5
1,?4-?Benzenedicarboxylic acid, 2,?5-?di-?1H-?imidazol-?1-?yl-?, 1,?4-?diethyl ester 1,?4-?Benzenedicarboxylic acid, 2,?5-?di-?1H-?imidazol-?1-?yl-?, 1,?4-?diethyl ester 1942879-47-1 C18H18N4O4
3-Methyl-6-phenylimidazo[2,1-b][1,3]thiazol-5-amine 3-Methyl-6-phenylimidazo[2,1-b][1,3]thiazol-5-amine 94802-79-6 C12H11N3S
Pyrazolo[1,5-a]pyridine-3-carbonitrile, 7-bromo- Pyrazolo[1,5-a]pyridine-3-carbonitrile, 7-bromo- 1824091-22-6 C8H4BrN3
Pyridine, 2-[(4S)-4-(1,1-dimethylethyl)-4,5-dihydro-1-phenyl-1H-imidazol-2-yl]- Pyridine, 2-[(4S)-4-(1,1-dimethylethyl)-4,5-dihydro-1-phenyl-1H-imidazol-2-yl]- 2688032-35-9 C18H21N3
INDEX NAME NOT YET ASSIGNED INDEX NAME NOT YET ASSIGNED 2375720-19-5 C28H22N4O2
Carbamic acid, 3-furanyl-, 1,1-dimethylethyl ester (9CI) Carbamic acid, 3-furanyl-, 1,1-dimethylethyl ester (9CI) 56267-48-2 C9H13NO3
3-(1H-Imidazol-4-yl)pyridine 3-(1H-Imidazol-4-yl)pyridine 51746-85-1 C8H7N3
Pyrido[2,3-d]pyrimidin-4(3H)-one, 6-bromo-2,7-dimethyl- Pyrido[2,3-d]pyrimidin-4(3H)-one, 6-bromo-2,7-dimethyl- 2090991-89-0 C9H8BrN3O
9H-Carbazole, 2-[3-(1H-benzimidazol-1-yl)phenoxy]-9-[4-(1,1-dimethylethyl)-2-pyridinyl]- 9H-Carbazole, 2-[3-(1H-benzimidazol-1-yl)phenoxy]-9-[4-(1,1-dimethylethyl)-2-pyridinyl]- 2264042-89-7 C34H28N4O
2,4(3H,5H)-Pyrimidinedione, 6-amino- (9CI) 2,4(3H,5H)-Pyrimidinedione, 6-amino- (9CI) 14436-34-1 C4H5N3O2
4-(1H-Benzoimidazol-2-yl)-benzoic acid 4-(1H-Benzoimidazol-2-yl)-benzoic acid 66631-29-6 C14H10N2O2
4-AMINODIBENZOFURAN 4-AMINODIBENZOFURAN 50548-43-1 C12H9NO
2-(3-METHOXYPHENYL)PYRROLIDINE 2-(3-METHOXYPHENYL)PYRROLIDINE 103861-77-4 C11H15NO
Tolazoline Tolazoline C10H12N2
4,5,6,7-Tetrahydro-5-(triphenylmethyl)thieno[3,2-c]pyridine 4,5,6,7-Tetrahydro-5-(triphenylmethyl)thieno[3,2-c]pyridine 109904-25-8 C26H23NS
Imidazo[1,5-a]quinoline, 1-phenyl- Imidazo[1,5-a]quinoline, 1-phenyl- 148149-24-0 C17H12N2
7-HYDROXYBENZOFURAN 7-HYDROXYBENZOFURAN 4790-81-2 C8H6O2
2,3-Dihydro-2,2-dimethyl-7-benzofuranol 2,3-Dihydro-2,2-dimethyl-7-benzofuranol 1563-38-8 C10H12O2
Benzoguanamine Benzoguanamine 91-76-9 C9H9N5
Piperonyl aldehyde Piperonyl aldehyde 120-57-0 C8H6O3
Pseudothiohydantoin Pseudothiohydantoin 556-90-1 C3H4N2OS
Clopidol Clopidol 2971-90-6 C7H7Cl2NO
MORPHOLINE, POLYMER-BOUND MORPHOLINE, POLYMER-BOUND 138048-80-3 C4H9NO
FLUORENE-D10 FLUORENE-D10 81103-79-9 C13D10
3-Quinuclidinyl benzilate 3-Quinuclidinyl benzilate 6581-06-2 C21H23NO3
ISOSAFROLE ISOSAFROLE 120-58-1 C10H10O2
Pridine pury Pridine pury
Safrole Safrole 94-59-7 C10H10O2
thiazine thiazine 11084-06-3 C4H5NS
2-AMINO-4,5-DIHYDRO-1,3-THIAZOL-4-ONE HYDROCHLORIDE 2-AMINO-4,5-DIHYDRO-1,3-THIAZOL-4-ONE HYDROCHLORIDE 2192-06-5 C3H5ClN2OS
Dihydroxydimethyl melamine Dihydroxydimethyl melamine C5H14N6O2
4,7-Dichloroquinoline 4,7-Dichloroquinoline 1138471-54-1 C9H5Cl2N
5-(4-METHOXYPHENYL)-2-THIOPHENECARBOHYDRAZIDE 5-(4-METHOXYPHENYL)-2-THIOPHENECARBOHYDRAZIDE 69202-24-0 C12H12N2O2S
1,3,5-Triazine, 2-phenyl- (9CI) 1,3,5-Triazine, 2-phenyl- (9CI) 1722-18-5 C9H7N3
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