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
1-Amino-2-methylpropan-2-ol 1-Amino-2-methylpropan-2-ol 2854-16-2 C4H11NO
3-(4-bromophenyl)-N-phenylcarbazole 3-(4-bromophenyl)-N-phenylcarbazole 1028647-93-9 C24H16BrN
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
1-Boc-pyrrolidine-3-carboxylic acid 1-Boc-pyrrolidine-3-carboxylic acid 59378-75-5 C10H17NO4
2,2,6,6-Tetramethylpiperidinooxy 2,2,6,6-Tetramethylpiperidinooxy 2564-83-2 C9H18NO *
5-Azaindole 5-Azaindole 271-34-1 C7H6N2
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
(R)-(-)-3-Hydroxytetrahydrofuran (R)-(-)-3-Hydroxytetrahydrofuran 86087-24-3 C4H8O2
1-Boc-3-piperidone 1-Boc-3-piperidone 98977-36-7 C10H17NO3
2-Acetyl-6-methoxynaphthalene 2-Acetyl-6-methoxynaphthalene 3900-45-6 C13H12O2
Morpholine Morpholine 110-91-8 C4H9NO
Furfural Furfural 98-01-1 C5H4O2
Indole Indole 120-72-9 C8H7N
Cyanuric chloride Cyanuric chloride 108-77-0 C3Cl3N3
Thiazole Thiazole 288-47-1 C3H3NS
4,7-Dichloroquinoline 4,7-Dichloroquinoline 86-98-6 C9H5Cl2N
2-Aminopyridine 2-Aminopyridine 504-29-0 C5H6N2
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
Thiophene Thiophene 110-02-1 C4H4S
Carbazole Carbazole 86-74-8 C12H9N
Pyrrole Pyrrole 109-97-7 C4H5N
Fluorene Fluorene 86-73-7 C13H10
Coumarin Coumarin 91-64-5 C9H6O2
4,4'-Bipyridine 4,4'-Bipyridine 553-26-4 C10H8N2
Isoquinoline Isoquinoline 119-65-3 C9H7N
Melamine Melamine 108-78-1 C3H6N6
Furan Furan 110-00-9 C4H4O
3-Quinuclidinol 3-Quinuclidinol 1619-34-7 C7H13NO
1,3,5-Triazine 1,3,5-Triazine 290-87-9 C3H3N3
Acridine Acridine 260-94-6 C13H9N
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
(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
2,5-Bis(octyldithio)-1,3,4-thiadiazole 2,5-Bis(octyldithio)-1,3,4-thiadiazole 13539-13-4 C18H34N2S5
2,5-Dimethoxytetrahydrofuran 2,5-Dimethoxytetrahydrofuran 696-59-3 C6H12O3
2,3,3-Trimethylindolenine 2,3,3-Trimethylindolenine 1640-39-7 C11H13N
2-Methylindoline 2-Methylindoline 6872-06-6 C9H11N
Hexamethylol melamine Hexamethylol melamine
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
3,6-DI-4-PYRIDYL-1,2,4,5-TETRAZINE 3,6-DI-4-PYRIDYL-1,2,4,5-TETRAZINE 57654-36-1 C12H8N6
1,5-Diazabicyclo[4.3.0]non-5-ene 1,5-Diazabicyclo[4.3.0]non-5-ene 3001-72-7 C7H12N2
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
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
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
5-Methoxyindole 5-Methoxyindole 1006-94-6 C9H9NO
2-Methylindole 2-Methylindole 95-20-5 C9H9N
5-Chlorooxindole 5-Chlorooxindole 17630-75-0 C8H6ClNO
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
4-(CHLOROMETHYL)-2-(2-FURYL)-1,3-THIAZOLE 4-(CHLOROMETHYL)-2-(2-FURYL)-1,3-THIAZOLE 13386-49-7 C8H6ClNOS
1H-Isoindol-1-one,2,3-dihydro-4-methoxy-(9CI) 1H-Isoindol-1-one,2,3-dihydro-4-methoxy-(9CI) 366453-22-7 C9H9NO2
7-Bromoindole 7-Bromoindole 51417-51-7 C8H6BrN
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
4-Bromoindole 4-Bromoindole 52488-36-5 C8H6BrN
1,2-Dioxane 1,2-Dioxane 5703-46-8 C4H8O2
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
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-AMINO-5-BROMO-[1,3,4]THIADIAZOLE 2-AMINO-5-BROMO-[1,3,4]THIADIAZOLE 37566-39-5 C2H2BrN3S
Carbamic acid, 3-furanyl-, 1,1-dimethylethyl ester (9CI) Carbamic acid, 3-furanyl-, 1,1-dimethylethyl ester (9CI) 56267-48-2 C9H13NO3
(Diacetoxyiodo)benzene (Diacetoxyiodo)benzene 3240-34-4 C10H11IO4
2,3-Dihydro-2,2-dimethyl-7-benzofuranol 2,3-Dihydro-2,2-dimethyl-7-benzofuranol 1563-38-8 C10H12O2
2,4-Diamino-6-phenyl-1,3,5-triazine 2,4-Diamino-6-phenyl-1,3,5-triazine 91-76-9 C9H9N5
Piperonyl aldehyde Piperonyl aldehyde 120-57-0 C8H6O3
Pseudothiohydantoin Pseudothiohydantoin 556-90-1 C3H4N2OS
7-HYDROXYBENZOFURAN 7-HYDROXYBENZOFURAN 4790-81-2 C8H6O2
Clopidol Clopidol 2971-90-6 C7H7Cl2NO
MORPHOLINE, POLYMER-BOUND MORPHOLINE, POLYMER-BOUND 138048-80-3 C4H9NO
2-Amino-3,5-dinitrothiophene 2-Amino-3,5-dinitrothiophene 2045-70-7 C4H3N3O4S
Safrole Safrole 94-59-7 C10H10O2
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