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Heterocyclic Compounds

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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:
3-(4-bromophenyl)-N-phenylcarbazole
CAS:
1028647-93-9
MF:
C24H16BrN
Structure:
Chemical Name:
1-Amino-2-methylpropan-2-ol
CAS:
2854-16-2
MF:
C4H11NO
Structure:
Chemical Name:
5-Bromoindazole
CAS:
53857-57-1
MF:
C7H5BrN2
Structure:
Chemical Name:
3-Bromo-9H-carbazole
CAS:
1592-95-6
MF:
C12H8BrN
Structure:
Chemical Name:
(3aR,4S,7R,7aS) 4,7-Methano-1H-isoindole-1,3(2H)-dione
CAS:
14805-29-9
MF:
C9H11NO2
Structure:
Chemical Name:
3-BROMO-1H-PYRAZOLE
CAS:
14521-80-3
MF:
C3H3BrN2
Structure:
Chemical Name:
7-Azaindole
CAS:
271-63-6
MF:
C7H6N2
Structure:
Chemical Name:
3,3-DIFLUOROPYRROLIDINE HYDROCHLORIDE
CAS:
163457-23-6
MF:
C4H7F2N.ClH
Structure:
Chemical Name:
2-Piperidone
CAS:
675-20-7
MF:
C5H9NO
Structure:
Chemical Name:
6-Bromo-3-nitro-4-quinolinol
CAS:
853908-50-6
MF:
C9H5BrN2O3
Structure:
Chemical Name:
6-Bromoindazole
CAS:
79762-54-2
MF:
C7H5BrN2
Structure:
Chemical Name:
9-Phenyl-9H-carbazol-3-ylboronic acid
CAS:
854952-58-2
MF:
C18H14BNO2
Structure:
Chemical Name:
(S)-3-Hydroxypyrrolidine hydrochloride
CAS:
122536-94-1
MF:
C4H10ClNO
Structure:
Chemical Name:
THIAZOLIDINE
CAS:
504-78-9
MF:
C3H7NS
Structure:
Chemical Name:
Oxetan-3-ol
CAS:
7748-36-9
MF:
C3H6O2
Structure:
Chemical Name:
4-Chloro-7-azaindole
CAS:
55052-28-3
MF:
C7H5ClN2
Structure:
Chemical Name:
1-Boc-pyrrolidine-3-carboxylic acid
CAS:
59378-75-5
MF:
C10H17NO4
Structure:
Chemical Name:
Cyanuric fluoride
CAS:
675-14-9
MF:
C3F3N3
Structure:
Chemical Name:
4,4'-Bipyridine
CAS:
553-26-4
MF:
C10H8N2
Structure:
Chemical Name:
Isoquinoline
CAS:
119-65-3
MF:
C9H7N
Structure:
Chemical Name:
Coumarin
CAS:
91-64-5
MF:
C9H6O2
Structure:
Chemical Name:
Fluorene
CAS:
86-73-7
MF:
C13H10
Structure:
Chemical Name:
Pyrrole
CAS:
109-97-7
MF:
C4H5N
Structure:
Chemical Name:
5-Bromoindole
CAS:
10075-50-0
MF:
C8H6BrN
Structure:
Chemical Name:
Carbazole
CAS:
86-74-8
MF:
C12H9N
Structure:
Chemical Name:
Thiophene
CAS:
110-02-1
MF:
C4H4S
Structure:
Chemical Name:
2,2,6,6-Tetramethylpiperidinooxy
CAS:
2564-83-2
MF:
C9H18NO*
Structure:
Chemical Name:
Melamine
CAS:
108-78-1
MF:
C3H6N6
Structure:
Chemical Name:
4,7-Dichloroquinoline
CAS:
86-98-6
MF:
C9H5Cl2N
Structure:
Chemical Name:
5-Azaindole
CAS:
271-34-1
MF:
C7H6N2
Structure:
Chemical Name:
2,6-Lutidine
CAS:
108-48-5
MF:
C7H9N
Structure:
Chemical Name:
2,4,6-Collidine
CAS:
108-75-8
MF:
C8H11N
Structure:
Chemical Name:
Tetrahydrofuran
CAS:
109-99-9
MF:
C4H8O
Structure:
Chemical Name:
3,3'-Dibromo-2,2'-bithiophene
CAS:
51751-44-1
MF:
C8H4Br2S2
Structure:
Chemical Name:
Ethyl 3-amino-4-pyrazolecarboxylate
CAS:
6994-25-8
MF:
C6H9N3O2
Structure:
Chemical Name:
Thiazole
CAS:
288-47-1
MF:
C3H3NS
Structure:
Chemical Name:
2-Aminopyridine
CAS:
504-29-0
MF:
C5H6N2
Structure:
Chemical Name:
2-Acetyl-6-methoxynaphthalene
CAS:
3900-45-6
MF:
C13H12O2
Structure:
Chemical Name:
Indole
CAS:
120-72-9
MF:
C8H7N
Structure:
Chemical Name:
(R)-(-)-3-Hydroxytetrahydrofuran
CAS:
86087-24-3
MF:
C4H8O2
Structure:
Chemical Name:
1-Boc-3-piperidone
CAS:
98977-36-7
MF:
C10H17NO3
Structure:
Chemical Name:
Furfural
CAS:
98-01-1
MF:
C5H4O2
Structure:
Chemical Name:
Morpholine
CAS:
110-91-8
MF:
C4H9NO
Structure:
Chemical Name:
3-Quinuclidinol
CAS:
1619-34-7
MF:
C7H13NO
Structure:
Chemical Name:
Cyanuric chloride
CAS:
108-77-0
MF:
C3Cl3N3
Structure:
Chemical Name:
Furan
CAS:
110-00-9
MF:
C4H4O
Structure:
Chemical Name:
Acridine
CAS:
260-94-6
MF:
C13H9N
Structure:
Chemical Name:
(S)-2-(4-Fluorophenyl)pyrrolidine
CAS:
298690-90-1
MF:
C10H12FN
Structure:
Chemical Name:
6-phenyluracil
CAS:
13345-09-0
MF:
C10H8N2O2
Structure:
Chemical Name:
1-(3-Chlorophenyl)imidazolidin-2-one
CAS:
14088-98-3
MF:
C9H9ClN2O
Structure:
Chemical Name:
2-(3-pentenyl)pyridine
CAS:
2057-43-4
MF:
C10H13N
Structure:
Chemical Name:
1-ethyl-4-(2-morpholinoethyl)-3,3-diphenylpyrrolidin-2-one monohydrochloride
CAS:
113-07-5
MF:
C24H31ClN2O2
Structure:
Chemical Name:
(S)-2-methyl-6-(pyrrolidin-2-yl)pyridine
CAS:
1213442-21-7
MF:
C10H14N2
Structure:
Chemical Name:
1,3,5-triazine-2,4,6-triyltrinitrilohexamethanol
CAS:
531-18-0
MF:
C9H18N6O6
Structure:
Chemical Name:
(R)-(+)-1-[(1-METHYL-2-PYRROLIDINYL)METHYL]PIPERIDINE
CAS:
155726-05-9
MF:
C11H22N2
Structure:
Chemical Name:
(3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol
CAS:
5605-46-9
MF:
C12H17NO4S
Structure:
Chemical Name:
2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3S,4S)-
CAS:
905854-03-7
MF:
C23H19N3O2
Structure:
Chemical Name:
ethyl 7-(difluoromethyl)-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylate
CAS:
438219-16-0
MF:
C16H13F2N3O2
Structure:
Chemical Name:
2-CHLORO-5,6-DIMETHYLBENZIMIDAZOLE
CAS:
39791-96-3
MF:
C9H9ClN2
Structure:
Chemical Name:
1,3 dimethyl-5fluoropyrazol fluoride
MF:
C5H8F2N2
Structure:
Chemical Name:
5-CYCLOPROPYL-3-TRIFLUOROMETHYL-1H-PYRAZOLE
CAS:
1027617-86-2
MF:
C7H7F3N2
Structure:
Chemical Name:
1,3-pyrrolidinedicarboxylic acid, 4-methyl-, 1-(1,1-dimethylethyl) ester, (3r,4r)-rel-
CAS:
1253791-53-5
MF:
C11H19NO4
Structure:
Chemical Name:
4,4'-Bi-4H-1,2,4-triazole
CAS:
16227-15-9
MF:
C4H4N6
Structure:
Chemical Name:
S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid
CAS:
1255936-24-3
MF:
C13H14BrN3
Structure:
Chemical Name:
8-Azaspiro[Bicyclo[3.2.1]Octane-3,4'-Imidazolidine]-2',5'-Dione
CAS:
77398-55-1
MF:
C9H14ClN3O2
Structure:
Chemical Name:
trimorpholylmethane
CAS:
22630-09-7
MF:
C13H25N3O3
Structure:
Chemical Name:
2,5-Pyrrolidinedione, 1-[(4-chlorobenzoyl)oxy]-
CAS:
68388-09-0
MF:
C11H8ClNO4
Structure:
Chemical Name:
3-Pyrrolidinol, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-, (3R,5S)-
CAS:
260417-94-5
MF:
C11H25NO2Si
Structure:
Chemical Name:
2,3-Dibromo-5,6,7,8-tetrahydroimidazo-[1,2-a]pyridine
CAS:
156817-73-1
MF:
C7H8Br2N2
Structure:
Chemical Name:
4-Chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine
CAS:
870706-47-1
MF:
C9H10ClN3
Structure:
Chemical Name:
Thiazolo[4,5-d]pyrimidin-2-amine, 7-chloro-5-[[(1S)-1-phenylethyl]thio]-
CAS:
911820-08-1
MF:
C13H11ClN4S2
Structure:
Chemical Name:
2,4,6-tris(4-pyrazol-1-yl)-1,3,5-triazine
CAS:
27257-90-5
MF:
C12H9N9
Structure:
Chemical Name:
MK-8031
CAS:
1374248-81-3
MF:
C29H23F6N5O3
Structure:
Chemical Name:
4-Phenyl-2(3H)-thiazolone
CAS:
3884-31-9
MF:
C9H7NOS
Structure:
Chemical Name:
6-Nitroindazole
CAS:
7597-18-4
MF:
C7H5N3O2
Structure:
Chemical Name:
8-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyridine
CAS:
1206981-68-1
MF:
C8H4BrF3N2
Structure:
Chemical Name:
5-CYCLOPROPYL-2H-PYRAZOL-3-YLAMINE
CAS:
175137-46-9
MF:
C6H9N3
Structure:
Chemical Name:
5-FLUORO-1H-BENZIMIDAZOLE-2-AMINE
CAS:
30486-73-8
MF:
C7H6FN3
Structure:
Chemical Name:
2-(Aminomethyl)-1-Boc-piperidine
CAS:
370069-31-1
MF:
C11H22N2O2
Structure:
Chemical Name:
Imidazo[1,2-a]pyridin-7-ol
CAS:
896139-85-8
MF:
C7H6N2O
Structure:
Chemical Name:
1,3,5-Triazine
CAS:
290-87-9
MF:
C3H3N3
Structure:
Chemical Name:
2,4,6-trimethyl-1,3,5-triazine
CAS:
823-94-9
MF:
C6H9N3
Structure:
Chemical Name:
2α-Formylpyrrolidine-1-carboxylic acid benzyl ester
CAS:
71461-30-8
MF:
C13H15NO3
Structure:
Chemical Name:
2,4-DIHYDROXY-6-NITROQUINAZOLINE
CAS:
32618-85-2
MF:
C8H5N3O4
Structure:
Chemical Name:
(S)-1-N-Boc-2-methylpiperazine
CAS:
169447-70-5
MF:
C10H20N2O2
Structure:
Chemical Name:
3,5-DIMETHYL-1-PHENYLPYRAZOLE
CAS:
1131-16-4
MF:
C11H12N2
Structure:
Chemical Name:
1-[[2,4,6-Tris(isopropyl)phenyl]sulphonyl]-1H-1,2,4-triazole
CAS:
54230-60-3
MF:
C17H25N3O2S
Structure:
Chemical Name:
4-ACETYL-5-METHYL-1-PHENYLPYRAZOLE
CAS:
6123-63-3
MF:
C12H12N2O
Structure:
Chemical Name:
(3R)-(+)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE
CAS:
131878-23-4
MF:
C16H24N2O2
Structure:
Chemical Name:
(R)-3-AMINOMETHYL-1-CBZ-PYRROLIDINE
CAS:
1217749-69-3
MF:
C13H18N2O2
Structure:
Chemical Name:
5-(3-BROMO-PHENYL)-1H-PYRAZOLE
CAS:
149739-65-1
MF:
C9H7BrN2
Structure:
Chemical Name:
5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE
CAS:
5334-43-0
MF:
C10H8N4
Structure:
Chemical Name:
2,2'-Bioxazole, 4,4',5,5'-tetrahydro-4,4'-bis[(1S)-1-methylpropyl]-, (4S,4'S)-
CAS:
133463-89-5
MF:
C14H24N2O2
Structure:
Chemical Name:
1,4-bis(1-(4-methyl)imidazolyl)benzene
CAS:
1627843-75-7
MF:
C14H14N4
Structure:
Chemical Name:
4-(1H-IMIDAZOL-2-YL)-PYRIDINE
CAS:
21202-42-6
MF:
C8H7N3
Structure:
Chemical Name:
7-BROMO-4-CHLOROQUINAZOLINE
CAS:
573675-55-5
MF:
C8H4BrClN2
Structure:
Chemical Name:
7-Bromoquinazoline
CAS:
89892-22-8
MF:
C8H5BrN2
Structure:
Chemical Name:
N-METHYLFULLEROPYRROLIDINE
CAS:
151872-44-5
MF:
C63H7N
Structure:
Chemical Name:
(2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95%
CAS:
415678-40-9
MF:
C16H18N2O2
Structure:
Chemical Name:
4,7-dibromo-5,6-dinitro-2-octyl-2H-benzo[d][1,2,3]triazole
CAS:
1870070-11-3
MF:
C14H17Br2N5O4