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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-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
2-Oxa-6-azaspiro[3.4]octane hemioxalate 2-Oxa-6-azaspiro[3.4]octane hemioxalate 1523570-96-8 C8H13NO5
P4S10-Pyridine complex P4S10-Pyridine complex 16610-51-8 C10H10N2P2S5
1,1'-Thiocarbonyldiimidazole 1,1'-Thiocarbonyldiimidazole 6160-65-2 C7H6N4S
(R)-5-Hydroxymethyldihydrofuran-2-one (R)-5-Hydroxymethyldihydrofuran-2-one 52813-63-5 C5H8O3
(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
Octanoic acid, 8-oxo-8-(3-pyridinylamino)-, methyl ester
Octanoic acid, 8-oxo-8-(3-pyridinylamino)-, methyl ester 405096-07-3 C14H20N2O3
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
3-(bromomethyl)oxetane-3-carboxylic acid 3-(bromomethyl)oxetane-3-carboxylic acid 1802048-89-0 C5H7BrO3
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
3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid 652980-08-0 C9H4BrCl2N3O2
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
3',6'-dichlorospiro[benzo[c][1,2]oxathiole-3,9'-xanthene] 1,1-dioxide 3',6'-dichlorospiro[benzo[c][1,2]oxathiole-3,9'-xanthene] 1,1-dioxide 77545-45-0 C19H10Cl2O4S
8H-Benzofuro[2,3-c]carbazole 8H-Benzofuro[2,3-c]carbazole 1622290-43-0 C18H11NO
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
DBCO-(CH2)3-Acid DBCO-(CH2)3-Acid 1207355-31-4 C20H17NO3
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
6,7-Difluoro-4H-benzo[1,4]oxazin-3-one 6,7-Difluoro-4H-benzo[1,4]oxazin-3-one 865106-46-3 C8H5F2NO2
1-chloro-6-propan-2-ylisoquinoline 1-chloro-6-propan-2-ylisoquinoline 630422-59-2 C12H12ClN
2-(Cyanomethyl)benzimidazole 2-(Cyanomethyl)benzimidazole 4414-88-4 C9H7N3
5-(N-PHTHALIMIDO)-2-PENTANONE 5-(N-PHTHALIMIDO)-2-PENTANONE 3197-25-9 C13H13NO3
Arbidol Sulfoxide Arbidol Sulfoxide 151455-33-3 C22H25BrN2O4S
5-fluoro-1H-pyrimidine-2,4-dione 5-fluoro-1H-pyrimidine-2,4-dione 1189423-58-2 C4H3FN2O2
Oxymetazoline Oxymetazoline 1491-59-4 C16H24N2O
2-(2-AMINO-5-BROMOBENZOYL) PYRIDINE 2-(2-AMINO-5-BROMOBENZOYL) PYRIDINE 1563-56-0 C12H9BrN2O
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
2-Amino-3,5-dinitrothiophene 2-Amino-3,5-dinitrothiophene 2045-70-7 C4H3N3O4S
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
Safrole Safrole 94-59-7 C10H10O2
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
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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