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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-BROMO-1H-PYRAZOLE
CAS:
14521-80-3
MF:
C3H3BrN2
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:
7-Azaindole
CAS:
271-63-6
MF:
C7H6N2
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:
2-Piperidone
CAS:
675-20-7
MF:
C5H9NO
Structure:
Chemical Name:
3,3-DIFLUOROPYRROLIDINE HYDROCHLORIDE
CAS:
163457-23-6
MF:
C4H8ClF2N
Structure:
Chemical Name:
6-Bromo-3-nitro-4-quinolinol
CAS:
853908-50-6
MF:
C9H5BrN2O3
Structure:
Chemical Name:
5-Bromoindole
CAS:
10075-50-0
MF:
C8H6BrN
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:
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:
Carbazole
CAS:
86-74-8
MF:
C12H9N
Structure:
Chemical Name:
Thiophene
CAS:
110-02-1
MF:
C4H4S
Structure:
Chemical Name:
1-Boc-pyrrolidine-3-carboxylic acid
CAS:
59378-75-5
MF:
C10H17NO4
Structure:
Chemical Name:
2,2,6,6-Tetramethylpiperidinooxy
CAS:
2564-83-2
MF:
C9H18NO*
Structure:
Chemical Name:
1,5-Diazabicyclo[4.3.0]non-5-ene
CAS:
3001-72-7
MF:
C7H12N2
Structure:
Chemical Name:
Melamine
CAS:
108-78-1
MF:
C3H6N6
Structure:
Chemical Name:
4-CYANOPYRAZOLE
CAS:
31108-57-3
MF:
C4H3N3
Structure:
Chemical Name:
1-(4-FLUOROPHENYL)-5-PHENYL-1H-PYRAZOLE
CAS:
299162-83-7
MF:
C15H11FN2
Structure:
Chemical Name:
2-Azetidinemethanamine
CAS:
103550-76-1
MF:
C4H10N2
Structure:
Chemical Name:
1-PHENYL-3-(TRIFLUOROMETHYL)PYRAZOLE
CAS:
99498-65-4
MF:
C10H7F3N2
Structure:
Chemical Name:
4,7-Dichloroquinoline
CAS:
86-98-6
MF:
C9H5Cl2N
Chemical Name:
4-bromo-3-cyclohexyl-1-isopropyl-1H-pyrazole
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:
2,5-Bis(octyldithio)-1,3,4-thiadiazole
CAS:
13539-13-4
MF:
C18H34N2S5
Structure:
Chemical Name:
Domazoline
CAS:
6043-01-2
MF:
C14H20N2O2
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:
2,4-DICHLORO-5-FLUOROQUINAZOLINE
CAS:
87611-00-5
MF:
C8H3Cl2FN2
Structure:
Chemical Name:
5-Bromo-quinazoline
CAS:
958452-00-1
MF:
C8H5BrN2
Structure:
Chemical Name:
5-(Hydroxymethyl)-1-methyl-1H-pyrazole
CAS:
84547-61-5
MF:
C5H8N2O
Structure:
Chemical Name:
6-BROMO-2,4-DICHLOROQUINAZOLINE
CAS:
102393-82-8
MF:
C8H3BrCl2N2
Structure:
Chemical Name:
Quinazoline, 4-methyl- (6CI,7CI,8CI,9CI)
CAS:
700-46-9
MF:
C9H8N2
Structure:
Chemical Name:
1-(3,4-dimethyl-1H-pyrazol-1-yl)ethan-1-one
CAS:
856064-45-4
MF:
C7H10N2O
Structure:
Chemical Name:
1-(4-Bromophenyl)-1H-pyrazole
CAS:
13788-92-6
MF:
C9H7BrN2
Structure:
Chemical Name:
2,4-DICHLORO-6-FLUOROQUINAZOLINE
CAS:
134517-57-0
MF:
C8H3Cl2FN2
Structure:
Chemical Name:
6-Bromo-2-iodoquinazoline
CAS:
882670-93-1
MF:
C8H4BrIN2
Structure:
Chemical Name:
(S,S)-(-)-2,2'-ISOPROPYLIDENEBIS(4-TERT-BUTYL-2-OXAZOLINE)
CAS:
131833-93-7
MF:
C17H30N2O2
Structure:
Chemical Name:
4-(3-BROMO-PHENYL)-THIAZOL-2-YLAMINE
CAS:
105512-81-0
MF:
C9H7BrN2S
Structure:
Chemical Name:
2,4-Dimethylquinazoline
CAS:
703-63-9
MF:
C10H10N2
Structure:
Chemical Name:
2,4-DICHLORO-7-BROMOQUINAZOLINE
CAS:
959237-68-4
MF:
C8H3BrCl2N2
Structure:
Chemical Name:
1-tert-Butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
CAS:
1256359-15-5
MF:
C13H23BN2O2
Structure:
Chemical Name:
(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile
CAS:
1146629-84-6
MF:
C17H26BN3O2
Structure:
Chemical Name:
1-tert-butyl-5-chloro-1H-pyrazole-4-carbonitrile
CAS:
1050619-87-8
MF:
C8H10ClN3
Structure:
Chemical Name:
6-BroMo-2-chloro-8-fluoroquinazoline
CAS:
953039-25-3
MF:
C8H3BrClFN2
Structure:
Chemical Name:
2-(4-Bromophenyl)-4-phenylquinazoline
CAS:
540466-42-0
MF:
C20H13BrN2
Structure:
Chemical Name:
1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole
CAS:
575452-22-1
MF:
C7H11IN2O
Structure:
Chemical Name:
1,4-Di(1H-pyrazol-4-yl)benzene
CAS:
1036248-62-0
MF:
C12H10N4
Structure:
Chemical Name:
4-Methoxyindole
CAS:
4837-90-5
MF:
C9H9NO
Structure:
Chemical Name:
1-tert-Butyl-4-iodo-1H-pyrazole
CAS:
1354705-41-1
MF:
C7H11IN2
Structure:
Chemical Name:
1,3-DIMETHYL-4-NITRO-1H-PYRAZOLE
CAS:
3920-38-5
MF:
C5H7N3O2
Structure:
Chemical Name:
1,3-DIMETHYL-1H-PYRAZOLE-5-CARBONITRILE
CAS:
306936-77-6
MF:
C6H7N3
Structure:
Chemical Name:
1,3-Dioxolane
CAS:
646-06-0
MF:
C3H6O2
Structure:
Chemical Name:
Boron trifluoride tetrahydrofuran complex
CAS:
462-34-0
MF:
C4H8BF3O
Structure:
Chemical Name:
PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE
CAS:
159326-68-8
MF:
C6H6N4
Structure:
Chemical Name:
4-Thiazolecarboxylic acid
CAS:
3973-08-8
MF:
C4H3NO2S
Chemical Name:
Fenoxazoline
Structure:
Chemical Name:
Midodrine hydrochloride
CAS:
3092-17-9
MF:
C12H19ClN2O4
Structure:
Chemical Name:
4-CHLORO-2-PHENYLQUINAZOLINE
CAS:
6484-25-9
MF:
C14H9ClN2
Structure:
Chemical Name:
QUINAZOLINE, 4-CHLORO-6-FLUORO-2-(TRIFLUOROMETHYL)-
CAS:
959238-11-0
MF:
C9H3ClF4N2
Structure:
Chemical Name:
3-(1-methylethyl)-pyrazole
CAS:
49633-25-2
MF:
C6H10N2
Structure:
Chemical Name:
2,5-DIPHENYLFURAN
CAS:
955-83-9
MF:
C16H12O
Structure:
Chemical Name:
4-Amino-8-bromo-2-chloroquinazoline
CAS:
956100-62-2
MF:
C8H5BrClN3
Structure:
Chemical Name:
1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid
CAS:
268545-13-7
MF:
C21H24FN3O4
Structure:
Chemical Name:
1-tert-Butyl-1H-pyrazole
CAS:
15754-60-6
MF:
C7H12N2
Structure:
Chemical Name:
1-tert-butyl-3-phenyl-1H-pyrazole
CAS:
1269293-29-9
MF:
C13H16N2
Structure:
Chemical Name:
2-Ethyl-2-oxazoline
CAS:
10431-98-8
MF:
C5H9NO
Structure:
Chemical Name:
3-(2-chloropyriMidin-4-yl)-1-Methylindole
CAS:
1032452-86-0
MF:
C13H10ClN3
Structure:
Chemical Name:
MMB-2201
CAS:
1616253-26-9
MF:
C20H27FN2O3
Structure:
Chemical Name:
5-BroMo-2-chloro-thiazolo[5,4-b]pyridine
CAS:
1355241-50-7
MF:
C6H2BrClN2S
Structure:
Chemical Name:
2,5-Dimethoxytetrahydrofuran
CAS:
696-59-3
MF:
C6H12O3
Structure:
Chemical Name:
5-CHLORO-1,3-DIMETHYLPYRAZOLE
CAS:
54454-10-3
MF:
C5H7ClN2
Structure:
Chemical Name:
2,3,3-Trimethylindolenine
CAS:
1640-39-7
MF:
C11H13N
Structure:
Chemical Name:
4-CHLORO-2-HYDROXYQUINOLINE
CAS:
20146-59-2
MF:
C9H6ClNO