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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:
6-METHYL-2-(PIPERIDIN-4-YL)-1H-BENZO[D]IMIDAZOLE
CAS:
295790-48-6
MF:
C13H17N3
Structure:
Chemical Name:
1,6-Diazabicyclo[3.2.1]octane-2-carboxylic acid, 7-oxo-6-(sulfooxy)-, 2-[2-[(3S)-3-pyrrolidinylcarbonyl]hydrazide], (1R,2S,5R)-
CAS:
1452460-79-5
MF:
C12H19N5O7S
Structure:
Chemical Name:
1-METHYL-1H-BENZOIMIDAZOL-5-YLAMINE TRIHYDROCHLORIDE
CAS:
10394-38-4
MF:
C8H9N3
Structure:
Chemical Name:
2,4(1H,3H)-Pyrimidinedione, 1-cyclopentyl-
CAS:
13345-72-7
MF:
C9H12N2O2
Structure:
Chemical Name:
7-Bromo-1-methyl-1H-indole 97%
CAS:
280752-68-3
MF:
C9H8BrN
Structure:
Chemical Name:
7H-Pyrrolo[1,2-a]imidazol-7-one,5,6-dihydro-(9CI)
CAS:
112513-82-3
MF:
C6H6N2O
Structure:
Chemical Name:
3-Pyrrolidinamine,4-fluoro-,dihydrochloride,trans-(9CI)
CAS:
125197-40-2
MF:
C4H9FN2.2ClH
Structure:
Chemical Name:
1H-Benzimidazole,2-ethenyl-(9CI)
CAS:
14984-26-0
MF:
C9H8N2
Structure:
Chemical Name:
2H-Imidazo[4,5-b]pyridin-2-one,5-amino-1,3-dihydro-(9CI)
CAS:
40851-87-4
MF:
C6H6N4O
Structure:
Chemical Name:
2-Pyrrolidineethanamine,1-methyl-,(2R)-(9CI)
CAS:
422545-96-8
MF:
C7H16N2
Structure:
Chemical Name:
1H-Imidazo[4,5-c]pyridine,4-methoxy-(9CI)
CAS:
158089-18-0
MF:
C7H7N3O
Structure:
Chemical Name:
1H-Pyrrolo[2,3-d]pyrimidine-5-carboxylicacid,2-amino-4,7-dihydro-4-oxo-
CAS:
92636-62-9
MF:
C7H6N4O3
Structure:
Chemical Name:
3-Pyridinecarboxamide,2-amino-5-bromo-N-cyclopropyl-(9CI)
CAS:
781642-04-4
MF:
C9H10BrN3O
Structure:
Chemical Name:
2,6-Pyridinediamine,1-oxide(9CI)
CAS:
146538-81-0
MF:
C5H7N3O
Structure:
Chemical Name:
3-Chloro-1,2,4-triazole
CAS:
6818-99-1
MF:
C2H2ClN3
Chemical Name:
N-Methyl-Cyclazodone
Structure:
Chemical Name:
(R)-(-)-1-Benzyl-3-aminopyrrolidine
CAS:
114715-39-8
MF:
C11H16N2
Structure:
Chemical Name:
Poly urethane
CAS:
51852-81-4
MF:
C16H22N2O5
Structure:
Chemical Name:
5-methyl-1H-4-carboxylic acid
CAS:
1457-59-6
MF:
C5H6N2O2
Structure:
Chemical Name:
3-(1-pyrrolidinyl)propiophenone hydrochloride
CAS:
833-86-3
MF:
C13H17NO.ClH
Structure:
Chemical Name:
1-bromo-3-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,5-a]pyrazine hydrochloride
CAS:
2138351-97-8
MF:
C7H8BrClF3N3
Structure:
Chemical Name:
4,5-dihydro-2-(2-methoxyphenyl)-1-[2-(2-methoxyphenyl)-4,5-diphenyl-2H-imidazol-2-yl]-1H-imidazole
CAS:
7292-18-4
MF:
C32H28N4O2
Structure:
Chemical Name:
1-(methoxymethyl)-1H-imidazole
CAS:
20075-26-7
MF:
C5H8N2O
Structure:
Chemical Name:
1-(tert-butyl)pyrrolidin-2-one
CAS:
20687-53-0
MF:
C8H15NO
Structure:
Chemical Name:
N-acetylsulphanilic acid
CAS:
121-62-0
MF:
C8H9NO4S
Structure:
Chemical Name:
1-methyl-5-thioxopyrrolidin-2-one
CAS:
2043-24-5
MF:
C5H7NOS
Structure:
Chemical Name:
1-(3-METHYLPHENYL)-2-OXO-3-PYRROLIDINEC&
CAS:
618070-31-8
MF:
C12H13NO3
Structure:
Chemical Name:
(S)-4-bromo-1-(pyrrolidin-3-yl)-1H-pyrazole hydrochloride
CAS:
2828444-32-0
MF:
C7H11BrClN3
Structure:
Chemical Name:
2-Pyridinecarboximidic acid, 2-methylhydrazide
CAS:
28819-35-4
MF:
C7H10N4
Chemical Name:
(R)-4-iodo-1-(pyrrolidin-3-yl)-1H-pyrazole
Structure:
Chemical Name:
3,5-diphenyloxazole
CAS:
2039-49-8
MF:
C15H11NO
Structure:
Chemical Name:
1-(4-Bromophenyl)-1H-pyrazole
CAS:
13788-92-6
MF:
C9H7BrN2
Structure:
Chemical Name:
N,N-diethyl-3-methyl-4-[(5-nitro-1,3-thiazol-2-yl)diazenyl]aniline
CAS:
70693-64-0
MF:
C14H17N5O2S
Structure:
Chemical Name:
(S)-N-Phenyl-2-pyrrolidinecarboxamide
CAS:
64030-43-9
MF:
C11H14N2O
Structure:
Chemical Name:
2,4-DICHLORO-6-FLUOROQUINAZOLINE
CAS:
134517-57-0
MF:
C8H3Cl2FN2
Structure:
Chemical Name:
2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile
CAS:
775351-54-7
MF:
C14H18BNO2
Structure:
Chemical Name:
6-Bromo-2-iodoquinazoline
CAS:
882670-93-1
MF:
C8H4BrIN2
Structure:
Chemical Name:
4-Trifluoromethyl-pyridine-2-carbaldehyde
CAS:
132470-83-8
MF:
C7H4F3NO
Structure:
Chemical Name:
4-(Trifluoromethyl)pyridine-2-thiol
CAS:
121307-79-7
MF:
C6H4F3NS
Structure:
Chemical Name:
2H-PYRIMIDO[1,2-B]PYRIDAZIN, 2-CHLORO-7,8-DIMETHYL-
CAS:
17412-26-9
MF:
C8H8ClN3
Structure:
Chemical Name:
6-Aminoindazole
CAS:
6967-12-0
MF:
C7H7N3
Structure:
Chemical Name:
Azacyclotridecan-2-one
CAS:
947-04-6
MF:
C12H23NO
Structure:
Chemical Name:
(S,S)-(-)-2,2'-ISOPROPYLIDENEBIS(4-TERT-BUTYL-2-OXAZOLINE)
CAS:
131833-93-7
MF:
C17H30N2O2
Structure:
Chemical Name:
2,6-Dimethylbenzyl chloride
CAS:
5402-60-8
MF:
C9H11Cl
Structure:
Chemical Name:
4-(3-BROMO-PHENYL)-THIAZOL-2-YLAMINE
CAS:
105512-81-0
MF:
C9H7BrN2S
Structure:
Chemical Name:
7-(4-tert-Butylphenyl)-2-methyl-1H-indene
CAS:
245653-52-5
MF:
C20H22
Structure:
Chemical Name:
6-Methylimidazo[2,1-b]thiazole
CAS:
3835-41-4
MF:
C6H6N2S
Structure:
Chemical Name:
2,4-Dimethylquinazoline
CAS:
703-63-9
MF:
C10H10N2
Structure:
Chemical Name:
4-Methyl-6-ethoxypyrimidine-2-amine
CAS:
7749-48-6
MF:
C7H11N3O
Structure:
Chemical Name:
5-NITRO-1H-BENZOIMIDAZOLE-2-CARBOXYLIC ACID
CAS:
73903-18-1
MF:
C8H5N3O4
Structure:
Chemical Name:
1-ALLYLPYRIMIDINE-2,4(1H,3H)-DIONE
CAS:
25855-26-9
MF:
C7H8N2O2
Structure:
Chemical Name:
2,4-DICHLORO-7-BROMOQUINAZOLINE
CAS:
959237-68-4
MF:
C8H3BrCl2N2
Structure:
Chemical Name:
8-METHYLIMIDAZO[1,2-A]PYRIDINE
CAS:
874-10-2
MF:
C8H8N2
Structure:
Chemical Name:
3-Bromo-5-chloroimidazo[1,2-a]pyridine
CAS:
1260656-94-7
MF:
C7H4BrClN2
Structure:
Chemical Name:
4-(morpholin-4-yl-phenoxy-phosphoryl)morpholine
CAS:
4881-17-8
MF:
C14H21N2O4P
Structure:
Chemical Name:
2-Mercaptobenzoxazole
CAS:
2382-96-9
MF:
C7H5NOS
Structure:
Chemical Name:
2-(METHYLTHIO)-2-IMIDAZOLINE
CAS:
20112-79-2
MF:
C4H8N2S
Structure:
Chemical Name:
3,4-Epoxytetrahydrofuran
CAS:
285-69-8
MF:
C4H6O2
Structure:
Chemical Name:
7-METHYL-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID
CAS:
80353-94-2
MF:
C9H8N2O2
Structure:
Chemical Name:
2,4-DICHLORO-5-FLUOROQUINAZOLINE
CAS:
87611-00-5
MF:
C8H3Cl2FN2
Structure:
Chemical Name:
6,8-Dibromo-2-trifluoromethylimidazo[1,2-a]pyrazine
CAS:
1208082-24-9
MF:
C7H2Br2F3N3
Structure:
Chemical Name:
5-(Trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid
CAS:
1260798-62-6
MF:
C9H5F3N2O2
Structure:
Chemical Name:
BOC-4-HYDROXY-L-PYRROLIDINE LACTONE
CAS:
113775-22-7
MF:
C10H15NO4
Structure:
Chemical Name:
4-(1-BUTENYL PENTENYL) PYRIDINE
CAS:
2057-34-3
MF:
C14H19N
Structure:
Chemical Name:
5',3'']Terpyridine
CAS:
106047-31-8
MF:
C15H11N3
Structure:
Chemical Name:
2,3,4-trimethyl-5,6-diphenylpyridine
CAS:
1004547-55-0
MF:
C20H19N
Structure:
Chemical Name:
MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER
CAS:
212650-43-6
MF:
C10H17NO5
Structure:
Chemical Name:
(R)-4-BENZYL-1,3-OXAZOLIDINE-2-THIONE
CAS:
190970-58-2
MF:
C10H11NOS
Structure:
Chemical Name:
2-Methyl-4-phenyl-1H-imidazole
CAS:
13739-48-5
MF:
C10H10N2
Structure:
Chemical Name:
1H-1,2,4-Triazole-3,5-diamine
CAS:
1455-77-2
MF:
C2H5N5
Structure:
Chemical Name:
1-(4-Nitrophenyl)-1H-pyrazole
CAS:
3463-30-7
MF:
C9H7N3O2
Structure:
Chemical Name:
5-(CHLOROMETHYL)-1,3-DIMETHYL-1H-PYRAZOLE
CAS:
852227-86-2
MF:
C6H9ClN2
Structure:
Chemical Name:
(1,3-DIMETHYL-1H-PYRAZOL-5-YL)METHANOL
CAS:
57012-20-1
MF:
C6H10N2O
Structure:
Chemical Name:
Pyrrolo[1,2-c]pyrimidine-3-carboxylic acid (9CI)
CAS:
251102-27-9
MF:
C8H6N2O2
Structure:
Chemical Name:
Pyrrolidine, 2-(2-fluorophenyl)-4-methyl- (9CI)
CAS:
603068-40-2
MF:
C11H14FN
Structure:
Chemical Name:
1H-Imidazole-1-propanoic acid, α-cyclopropyl-α-(methylamino)-
CAS:
1338993-61-5
MF:
C10H15N3O2
Structure:
Chemical Name:
1-Pyrrolidinecarboxylic acid, 3-(difluoromethyl)-4-hydroxy-, 1,1-dimethylethyl ester, (3R,4S)-rel-
CAS:
2368911-11-7
MF:
C10H17F2NO3
Structure:
Chemical Name:
2-Pyrrolidinemethanol, 1-methyl-4-(trifluoromethyl)-, (2S,4R)-
CAS:
2621932-86-1
MF:
C7H12F3NO
Chemical Name:
2,4-diamino-6-chloropyrimidine-1-oxide
Chemical Name:
6-bromo-2-fluoro-3-(3-(pyrrolidin-1-yl)propoxy)benzonitrile
Structure:
Chemical Name:
5-Bromo-quinazoline
CAS:
958452-00-1
MF:
C8H5BrN2
Structure:
Chemical Name:
3-(1H-Benzimidazol-1-yl)propanenitrile
CAS:
4414-84-0
MF:
C10H9N3
Structure:
Chemical Name:
1-hydroxybenzotriazole monohydrate
MF:
C6H7N3O2
Structure:
Chemical Name:
4-Bromo-5-methyl-1H-pyrazol-3-amine
CAS:
1780-72-9
MF:
C4H6BrN3
Structure:
Chemical Name:
1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione
CAS:
206055-67-6
MF:
C11H14N2O6
Structure:
Chemical Name:
3-IODO-6-METHYL-IMIDAZO[1,2-A]PYRIDINE
CAS:
885276-23-3
MF:
C8H7IN2
Structure:
Chemical Name:
5-Methoxyindole
CAS:
1006-94-6
MF:
C9H9NO
Structure:
Chemical Name:
2-(4-CHLORO-PHENYL)-IMIDAZO[1,2-A]PYRIDINE
CAS:
38922-74-6
MF:
C13H9ClN2
Structure:
Chemical Name:
3-BROMO-1-(TRIISOPROPYLSILYL)PYRROLE
CAS:
87630-36-2
MF:
C13H24BrNSi
Structure:
Chemical Name:
1-[(4-Nitrophenyl)methyl]pyrazole
CAS:
110525-57-0
MF:
C10H9N3O2
Structure:
Chemical Name:
3,5-Diamino-1H-pyrazole
CAS:
16082-33-0
MF:
C3H6N4
Structure:
Chemical Name:
5-(CHLOROMETHYL)PYRIDINE-2-CARBALDEHYDE
CAS:
754920-10-0
MF:
C7H6ClNO
Structure:
Chemical Name:
5-Fluorothiophene-2-carbonitrile
CAS:
32415-91-1
MF:
C5H2FNS
Structure:
Chemical Name:
2,4-DICHLORO-7-IODO-5H-PYRROLO[3,2-D]PYRIMIDINE
CAS:
928840-99-7
MF:
C6H2Cl2IN3
Structure:
Chemical Name:
3-CHLOROMETHYL-PYRROLIDINE
CAS:
876509-14-7
MF:
C5H10ClN
Structure:
Chemical Name:
2,6-DICHLORO-N-METHYL-4-PYRIMIDINAMINE
CAS:
32998-03-1
MF:
C5H5Cl2N3
Structure:
Chemical Name:
[4-(2-AMINO-ETHYL)-PHENYL]-CARBAMIC ACID TERT-BUTYL ESTER
CAS:
457631-44-6
MF:
C13H20N2O2
Structure:
Chemical Name:
N-BOC-3-BROMO-4-HYDROXY-PYRROLIDINE
CAS:
1017782-17-0
MF:
C9H16BrNO3
Structure:
Chemical Name:
6-Amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol
CAS:
7400-06-8
MF:
C10H17N3O3
Structure:
Chemical Name:
1H-pyrazole, 4-iodo-1,3-dimethyl-
CAS:
6647-97-8
MF:
C5H7IN2