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-BROMO-1H-PYRAZOLE 3-BROMO-1H-PYRAZOLE 14521-80-3 C3H3BrN2
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
7-Azaindole 7-Azaindole 271-63-6 C7H6N2
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 C4H8ClF2N
2-Piperidone 2-Piperidone 675-20-7 C5H9NO
6-Bromo-3-nitro-4-quinolinol 6-Bromo-3-nitro-4-quinolinol 853908-50-6 C9H5BrN2O3
5-Bromoindole 5-Bromoindole 10075-50-0 C8H6BrN
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
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
Carbazole Carbazole 86-74-8 C12H9N
Thiophene Thiophene 110-02-1 C4H4S
1-Boc-pyrrolidine-3-carboxylic acid 1-Boc-pyrrolidine-3-carboxylic acid 59378-75-5 C10H17NO4
3-(2-chloropyriMidin-4-yl)-1-Methylindole 3-(2-chloropyriMidin-4-yl)-1-Methylindole 1032452-86-0 C13H10ClN3
MMB-2201 MMB-2201 1616253-26-9
5-BroMo-2-chloro-thiazolo[5,4-b]pyridine 5-BroMo-2-chloro-thiazolo[5,4-b]pyridine 1355241-50-7 C6H2BrClN2S
2,2,6,6-Tetramethylpiperidinooxy 2,2,6,6-Tetramethylpiperidinooxy 2564-83-2 C9H18NO *
1,5-Diazabicyclo[4.3.0]non-5-ene 1,5-Diazabicyclo[4.3.0]non-5-ene 3001-72-7 C7H12N2
Melamine Melamine 108-78-1 C3H6N6
4,7-Dichloroquinoline 4,7-Dichloroquinoline 86-98-6 C9H5Cl2N
5-Azaindole 5-Azaindole 271-34-1 C7H6N2
2,5-Dimethoxytetrahydrofuran 2,5-Dimethoxytetrahydrofuran 696-59-3 C6H12O3
2,3,3-Trimethylindolenine 2,3,3-Trimethylindolenine 1640-39-7 C11H13N
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
2,5-Bis(octyldithio)-1,3,4-thiadiazole 2,5-Bis(octyldithio)-1,3,4-thiadiazole 13539-13-4 C18H34N2S5
3,3'-Dibromo-2,2'-bithiophene 3,3'-Dibromo-2,2'-bithiophene 51751-44-1 C8H4Br2S2
3-Boc-6-oxa-3-aza-bicyclo[3.1.0]hexane 3-Boc-6-oxa-3-aza-bicyclo[3.1.0]hexane 114214-49-2 C9H15NO3
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
7-Bromoindole 7-Bromoindole 51417-51-7 C8H6BrN
3,4-Dimethoxy-2-pyridinemethanol 3,4-Dimethoxy-2-pyridinemethanol 72830-08-1 C8H11NO3
1,1'-Thiocarbonyldiimidazole 1,1'-Thiocarbonyldiimidazole 6160-65-2 C7H6N4S
2,2,6-Trimethyl-4H-1,3-dioxin-4-one 2,2,6-Trimethyl-4H-1,3-dioxin-4-one 5394-63-8 C7H10O3
Carbamic acid, 3-furanyl-, 1,1-dimethylethyl ester (9CI) Carbamic acid, 3-furanyl-, 1,1-dimethylethyl ester (9CI) 56267-48-2 C9H13NO3
1H-Isoindol-1-one,2,3-dihydro-4-methoxy-(9CI) 1H-Isoindol-1-one,2,3-dihydro-4-methoxy-(9CI) 366453-22-7 C9H9NO2
4-(CHLOROMETHYL)-2-(2-FURYL)-1,3-THIAZOLE 4-(CHLOROMETHYL)-2-(2-FURYL)-1,3-THIAZOLE 13386-49-7 C8H6ClNOS
1-Methylimidazole 1-Methylimidazole 616-47-7 C4H6N2
9,9'-Bis([1,1'-biphenyl]-3-yl)-3,3'-bi-9H-carbazole 9,9'-Bis([1,1'-biphenyl]-3-yl)-3,3'-bi-9H-carbazole 1352040-89-1 C48H32N2
1-Methylindole 1-Methylindole 603-76-9 C9H9N
5-Chlorooxindole 5-Chlorooxindole 17630-75-0 C8H6ClNO
2-Methylindole 2-Methylindole 95-20-5 C9H9N
2-AMINO-5-BROMO-[1,3,4]THIADIAZOLE 2-AMINO-5-BROMO-[1,3,4]THIADIAZOLE 37566-39-5 C2H2BrN3S
2,3-Dihydro-2,2-dimethyl-7-benzofuranol 2,3-Dihydro-2,2-dimethyl-7-benzofuranol 1563-38-8 C10H12O2
3,4-Epoxytetrahydrofuran 3,4-Epoxytetrahydrofuran 285-69-8 C4H6O2
2,4-Diamino-6-phenyl-1,3,5-triazine 2,4-Diamino-6-phenyl-1,3,5-triazine 91-76-9 C9H9N5
(Diacetoxyiodo)benzene (Diacetoxyiodo)benzene 3240-34-4 C10H11IO4
1H-Indazole,5-broMo-4-fluoro- 1H-Indazole,5-broMo-4-fluoro- 1082041-85-7 C7H4BrFN2
3,6-DI-2-PYRIDYL-1,2,4,5-TETRAZINE 3,6-DI-2-PYRIDYL-1,2,4,5-TETRAZINE 1671-87-0 C12H8N6
12H-Benzofuro[2,3-a]carbazole 12H-Benzofuro[2,3-a]carbazole 1338919-70-2 C18H11NO
2-Bromo-1,3-benzothiazole 2-Bromo-1,3-benzothiazole 2516-40-7 C7H4BrNS
ETHYL IMIDAZO[1,2-A]PYRAZINE-2-CARBOXYLATE ETHYL IMIDAZO[1,2-A]PYRAZINE-2-CARBOXYLATE 77112-52-8 C9H9N3O2
4-Bromoindole 4-Bromoindole 52488-36-5 C8H6BrN
1,2-Dioxane 1,2-Dioxane 5703-46-8 C4H8O2
Piperonyl aldehyde Piperonyl aldehyde 120-57-0 C8H6O3
5-Methoxyindole 5-Methoxyindole 1006-94-6 C9H9NO
2,3-Dihydrofuran 2,3-Dihydrofuran 1191-99-7 C4H6O
6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE 6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE 1745-07-9 C11H15NO2
Pseudothiohydantoin Pseudothiohydantoin 556-90-1 C3H4N2OS
4-Methoxyindole 4-Methoxyindole 4837-90-5 C9H9NO
2-Amino-5-methylthiazole 2-Amino-5-methylthiazole 7305-71-7 C4H6N2S
1,3-Dioxolane 1,3-Dioxolane 646-06-0 C3H6O2
Boron trifluoride tetrahydrofuran complex Boron trifluoride tetrahydrofuran complex 462-34-0 C4H8BF3O
PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE 159326-68-8 C6H6N4
4-Thiazolecarboxylic acid 4-Thiazolecarboxylic acid 3973-08-8 C4H3NO2S
3,6-DI-4-PYRIDYL-1,2,4,5-TETRAZINE 3,6-DI-4-PYRIDYL-1,2,4,5-TETRAZINE 57654-36-1 C12H8N6
Hexamethylol melamine Hexamethylol melamine
2-Methylindoline 2-Methylindoline 6872-06-6 C9H11N
(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide (R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide 473727-83-2 C21H23N3O5
3-chloro-2-methoxybenzoic acid 3-chloro-2-methoxybenzoic acid 3260-93-3 C8H7ClO3
1,3,5-Triazine 1,3,5-Triazine 290-87-9 C3H3N3
4,7-dibroMobenzo[1,2-c:4,5-c']bis([1,2,5]thiadiazole) 4,7-dibroMobenzo[1,2-c:4,5-c']bis([1,2,5]thiadiazole) 165617-59-4 C6Br2N4S2
1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE 1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE 85909-08-6 C9H15NO3
BIS(2-FURYL)CHLOROPHOSPHINE BIS(2-FURYL)CHLOROPHOSPHINE 181257-35-2 C8H6ClO2P
6-Bromo-1H-indole 6-Bromo-1H-indole 52415-29-9 C8H6BrN
Acridine Acridine 260-94-6 C13H9N
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