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-(4-bromophenyl)-N-phenylcarbazole 3-(4-bromophenyl)-N-phenylcarbazole 1028647-93-9 C24H16BrN
1-Amino-2-methylpropan-2-ol 1-Amino-2-methylpropan-2-ol 2854-16-2 C4H11NO
3-BROMO-1H-PYRAZOLE 3-BROMO-1H-PYRAZOLE 14521-80-3 C3H3BrN2
5-Bromoindazole 5-Bromoindazole 53857-57-1 C7H5BrN2
3-Bromo-9H-carbazole 3-Bromo-9H-carbazole 1592-95-6 C12H8BrN
(3aR,4S,7R,7aS)  4,7-Methano-1H-isoindole-1,3(2H)-dione (3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione 14805-29-9 C9H11NO2
3,3-DIFLUOROPYRROLIDINE HYDROCHLORIDE 3,3-DIFLUOROPYRROLIDINE HYDROCHLORIDE 163457-23-6 C4H7F2N.ClH
7-Azaindole 7-Azaindole 271-63-6 C7H6N2
2-Piperidone 2-Piperidone 675-20-7 C5H9NO
6-Bromo-3-nitro-4-quinolinol 6-Bromo-3-nitro-4-quinolinol 853908-50-6 C9H5BrN2O3
6-Bromoindazole 6-Bromoindazole 79762-54-2 C7H5BrN2
9-Phenyl-9H-carbazol-3-ylboronic acid 9-Phenyl-9H-carbazol-3-ylboronic acid 854952-58-2 C18H14BNO2
(S)-3-Hydroxypyrrolidine hydrochloride (S)-3-Hydroxypyrrolidine hydrochloride 122536-94-1 C4H10ClNO
THIAZOLIDINE THIAZOLIDINE 504-78-9 C3H7NS
Oxetan-3-ol Oxetan-3-ol 7748-36-9 C3H6O2
4-Chloro-7-azaindole 4-Chloro-7-azaindole 55052-28-3 C7H5ClN2
1-Boc-pyrrolidine-3-carboxylic acid 1-Boc-pyrrolidine-3-carboxylic acid 59378-75-5 C10H17NO4
Cyanuric fluoride Cyanuric fluoride 675-14-9 C3F3N3
4,4'-Bipyridine 4,4'-Bipyridine 553-26-4 C10H8N2
Isoquinoline Isoquinoline 119-65-3 C9H7N
Coumarin Coumarin 91-64-5 C9H6O2
Fluorene Fluorene 86-73-7 C13H10
Pyrrole Pyrrole 109-97-7 C4H5N
5-Bromoindole 5-Bromoindole 10075-50-0 C8H6BrN
Carbazole Carbazole 86-74-8 C12H9N
Thiophene Thiophene 110-02-1 C4H4S
2,2,6,6-Tetramethylpiperidinooxy 2,2,6,6-Tetramethylpiperidinooxy 2564-83-2 C9H18NO*
Melamine Melamine 108-78-1 C3H6N6
4,7-Dichloroquinoline 4,7-Dichloroquinoline 86-98-6 C9H5Cl2N
5-Azaindole 5-Azaindole 271-34-1 C7H6N2
2,6-Lutidine 2,6-Lutidine 108-48-5 C7H9N
2,4,6-Collidine 2,4,6-Collidine 108-75-8 C8H11N
Tetrahydrofuran Tetrahydrofuran 109-99-9 C4H8O
3,3'-Dibromo-2,2'-bithiophene 3,3'-Dibromo-2,2'-bithiophene 51751-44-1 C8H4Br2S2
Ethyl 3-amino-4-pyrazolecarboxylate Ethyl 3-amino-4-pyrazolecarboxylate 6994-25-8 C6H9N3O2
Thiazole Thiazole 288-47-1 C3H3NS
2-Aminopyridine 2-Aminopyridine 504-29-0 C5H6N2
2-Acetyl-6-methoxynaphthalene 2-Acetyl-6-methoxynaphthalene 3900-45-6 C13H12O2
Indole Indole 120-72-9 C8H7N
(R)-(-)-3-Hydroxytetrahydrofuran (R)-(-)-3-Hydroxytetrahydrofuran 86087-24-3 C4H8O2
1-Boc-3-piperidone 1-Boc-3-piperidone 98977-36-7 C10H17NO3
Furfural Furfural 98-01-1 C5H4O2
Morpholine Morpholine 110-91-8 C4H9NO
3-Quinuclidinol 3-Quinuclidinol 1619-34-7 C7H13NO
Cyanuric chloride Cyanuric chloride 108-77-0 C3Cl3N3
Furan Furan 110-00-9 C4H4O
Acridine Acridine 260-94-6 C13H9N
(S)-2-(4-Fluorophenyl)pyrrolidine (S)-2-(4-Fluorophenyl)pyrrolidine 298690-90-1 C10H12FN
6-phenyluracil 6-phenyluracil 13345-09-0 C10H8N2O2
1-(3-Chlorophenyl)imidazolidin-2-one 1-(3-Chlorophenyl)imidazolidin-2-one 14088-98-3 C9H9ClN2O
2-(3-pentenyl)pyridine 2-(3-pentenyl)pyridine 2057-43-4 C10H13N
1-ethyl-4-(2-morpholinoethyl)-3,3-diphenylpyrrolidin-2-one monohydrochloride 1-ethyl-4-(2-morpholinoethyl)-3,3-diphenylpyrrolidin-2-one monohydrochloride 113-07-5 C24H31ClN2O2
(S)-2-methyl-6-(pyrrolidin-2-yl)pyridine (S)-2-methyl-6-(pyrrolidin-2-yl)pyridine 1213442-21-7 C10H14N2
1,3,5-triazine-2,4,6-triyltrinitrilohexamethanol 1,3,5-triazine-2,4,6-triyltrinitrilohexamethanol 531-18-0 C9H18N6O6
(R)-(+)-1-[(1-METHYL-2-PYRROLIDINYL)METHYL]PIPERIDINE (R)-(+)-1-[(1-METHYL-2-PYRROLIDINYL)METHYL]PIPERIDINE 155726-05-9 C11H22N2
(3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol (3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol 5605-46-9 C12H17NO4S
2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3S,4S)- 2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3S,4S)- 905854-03-7 C23H19N3O2
ethyl 7-(difluoromethyl)-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylate ethyl 7-(difluoromethyl)-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylate 438219-16-0 C16H13F2N3O2
2-CHLORO-5,6-DIMETHYLBENZIMIDAZOLE 2-CHLORO-5,6-DIMETHYLBENZIMIDAZOLE 39791-96-3 C9H9ClN2
1,3 dimethyl-5fluoropyrazol fluoride 1,3 dimethyl-5fluoropyrazol fluoride C5H8F2N2
5-CYCLOPROPYL-3-TRIFLUOROMETHYL-1H-PYRAZOLE 5-CYCLOPROPYL-3-TRIFLUOROMETHYL-1H-PYRAZOLE 1027617-86-2 C7H7F3N2
1,3-pyrrolidinedicarboxylic acid, 4-methyl-, 1-(1,1-dimethylethyl) ester, (3r,4r)-rel- 1,3-pyrrolidinedicarboxylic acid, 4-methyl-, 1-(1,1-dimethylethyl) ester, (3r,4r)-rel- 1253791-53-5 C11H19NO4
4,4'-Bi-4H-1,2,4-triazole
4,4'-Bi-4H-1,2,4-triazole 16227-15-9 C4H4N6
S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid 1255936-24-3 C13H14BrN3
8-Azaspiro[Bicyclo[3.2.1]Octane-3,4'-Imidazolidine]-2',5'-Dione 8-Azaspiro[Bicyclo[3.2.1]Octane-3,4'-Imidazolidine]-2',5'-Dione 77398-55-1 C9H14ClN3O2
trimorpholylmethane trimorpholylmethane 22630-09-7 C13H25N3O3
2,5-Pyrrolidinedione, 1-[(4-chlorobenzoyl)oxy]- 2,5-Pyrrolidinedione, 1-[(4-chlorobenzoyl)oxy]- 68388-09-0 C11H8ClNO4
3-Pyrrolidinol, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-, (3R,5S)- 3-Pyrrolidinol, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-, (3R,5S)- 260417-94-5 C11H25NO2Si
2,3-Dibromo-5,6,7,8-tetrahydroimidazo-[1,2-a]pyridine 2,3-Dibromo-5,6,7,8-tetrahydroimidazo-[1,2-a]pyridine 156817-73-1 C7H8Br2N2
4-Chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine 4-Chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine 870706-47-1 C9H10ClN3
Thiazolo[4,5-d]pyrimidin-2-amine, 7-chloro-5-[[(1S)-1-phenylethyl]thio]- Thiazolo[4,5-d]pyrimidin-2-amine, 7-chloro-5-[[(1S)-1-phenylethyl]thio]- 911820-08-1 C13H11ClN4S2
2,4,6-tris(4-pyrazol-1-yl)-1,3,5-triazine 2,4,6-tris(4-pyrazol-1-yl)-1,3,5-triazine 27257-90-5 C12H9N9
MK-8031 MK-8031 1374248-81-3 C29H23F6N5O3
4-Phenyl-2(3H)-thiazolone 4-Phenyl-2(3H)-thiazolone 3884-31-9 C9H7NOS
6-Nitroindazole 6-Nitroindazole 7597-18-4 C7H5N3O2
8-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyridine 8-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyridine 1206981-68-1 C8H4BrF3N2
5-CYCLOPROPYL-2H-PYRAZOL-3-YLAMINE 5-CYCLOPROPYL-2H-PYRAZOL-3-YLAMINE 175137-46-9 C6H9N3
5-FLUORO-1H-BENZIMIDAZOLE-2-AMINE 5-FLUORO-1H-BENZIMIDAZOLE-2-AMINE 30486-73-8 C7H6FN3
1,3-BIS(4-CHLOROPHENYL)IMIDAZOLIUM CHLORIDE 1,3-BIS(4-CHLOROPHENYL)IMIDAZOLIUM CHLORIDE 141556-46-9 C15H11Cl3N2
6-IODO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 6-IODO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 478040-59-4 C8H5IN2O2
Imidazo[1,2-a]pyridin-7-ol Imidazo[1,2-a]pyridin-7-ol 896139-85-8 C7H6N2O
1,3,5-Triazine 1,3,5-Triazine 290-87-9 C3H3N3
2,4,6-trimethyl-1,3,5-triazine 2,4,6-trimethyl-1,3,5-triazine 823-94-9 C6H9N3
2α-Formylpyrrolidine-1-carboxylic acid benzyl ester 2α-Formylpyrrolidine-1-carboxylic acid benzyl ester 71461-30-8 C13H15NO3
2,4-DIHYDROXY-6-NITROQUINAZOLINE 2,4-DIHYDROXY-6-NITROQUINAZOLINE 32618-85-2 C8H5N3O4
3,5-DIMETHYL-1-PHENYLPYRAZOLE 3,5-DIMETHYL-1-PHENYLPYRAZOLE 1131-16-4 C11H12N2
1-[[2,4,6-Tris(isopropyl)phenyl]sulphonyl]-1H-1,2,4-triazole 1-[[2,4,6-Tris(isopropyl)phenyl]sulphonyl]-1H-1,2,4-triazole 54230-60-3 C17H25N3O2S
4-ACETYL-5-METHYL-1-PHENYLPYRAZOLE 4-ACETYL-5-METHYL-1-PHENYLPYRAZOLE 6123-63-3 C12H12N2O
(3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE (3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE 131878-23-4 C16H24N2O2
(R)-3-AMINOMETHYL-1-CBZ-PYRROLIDINE (R)-3-AMINOMETHYL-1-CBZ-PYRROLIDINE 1217749-69-3 C13H18N2O2
5-(3-BROMO-PHENYL)-1H-PYRAZOLE 5-(3-BROMO-PHENYL)-1H-PYRAZOLE 149739-65-1 C9H7BrN2
5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE 5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE 5334-43-0 C10H8N4
2,2'-Bioxazole, 4,4',5,5'-tetrahydro-4,4'-bis[(1S)-1-methylpropyl]-, (4S,4'S)- 2,2'-Bioxazole, 4,4',5,5'-tetrahydro-4,4'-bis[(1S)-1-methylpropyl]-, (4S,4'S)- 133463-89-5 C14H24N2O2
1,4-bis(1-(4-methyl)imidazolyl)benzene 1,4-bis(1-(4-methyl)imidazolyl)benzene 1627843-75-7 C14H14N4
4-(1H-IMIDAZOL-2-YL)-PYRIDINE 4-(1H-IMIDAZOL-2-YL)-PYRIDINE 21202-42-6 C8H7N3
7-BROMO-4-CHLOROQUINAZOLINE 7-BROMO-4-CHLOROQUINAZOLINE 573675-55-5 C8H4BrClN2
7-Bromoquinazoline 7-Bromoquinazoline 89892-22-8 C8H5BrN2
N-METHYLFULLEROPYRROLIDINE N-METHYLFULLEROPYRROLIDINE 151872-44-5 C63H7N
(2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95% (2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95% 415678-40-9 C16H18N2O2
4,7-dibromo-5,6-dinitro-2-octyl-2H-benzo[d][1,2,3]triazole 4,7-dibromo-5,6-dinitro-2-octyl-2H-benzo[d][1,2,3]triazole 1870070-11-3 C14H17Br2N5O4
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