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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
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
(S)-1-Boc-3-hydroxymethyl-piperazine (S)-1-Boc-3-hydroxymethyl-piperazine 314741-40-7 C10H20N2O3
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
6-Methoxy-1H-indazole 6-Methoxy-1H-indazole 3522-07-4 C8H8N2O
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
5-METHYL-1H-PYRROLO[3,2-B]PYRIDINE 5-METHYL-1H-PYRROLO[3,2-B]PYRIDINE 4943-67-3 C8H8N2
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
1-(3,4-Dimethylphenyl)piperazine 1-(3,4-Dimethylphenyl)piperazine 1014-05-7 C12H18N2
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-Amino-3,5-dinitrothiophene 2-Amino-3,5-dinitrothiophene 2045-70-7 C4H3N3O4S
FLUORENE-D10 FLUORENE-D10 81103-79-9 C13D10
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
ETHYL 2-[BIS(2,2,2-TRIFLUOROETHYL)PHOSPHONO] PROPIONATE ETHYL 2-[BIS(2,2,2-TRIFLUOROETHYL)PHOSPHONO] PROPIONATE 107905-52-2 C9H13F6O5P
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
3-Quinuclidinyl benzilate 3-Quinuclidinyl benzilate 6581-06-2 C21H23NO3
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
ISOSAFROLE ISOSAFROLE 120-58-1 C10H10O2
Pridine pury Pridine pury
Safrole Safrole 94-59-7 C10H10O2
Pseudothiohydantoin Pseudothiohydantoin 556-90-1 C3H4N2OS
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
Clopidol Clopidol 2971-90-6 C7H7Cl2NO
1,3,5-Triazine, 2-phenyl- (9CI) 1,3,5-Triazine, 2-phenyl- (9CI) 1722-18-5 C9H7N3
MORPHOLINE, POLYMER-BOUND MORPHOLINE, POLYMER-BOUND 138048-80-3 C4H9NO
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