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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:
4H-Imidazo[4,5-c]pyridin-4-one, 3,5,6,7-tetrahydro-3-methyl-
CAS:
1369160-23-5
MF:
C7 H9 N3 O
Structure:
Chemical Name:
10-Bromonaphtho[1,2-b]benzofuran
CAS:
1846601-95-3
MF:
C16H9BrO
Structure:
Chemical Name:
(2S,3R)-2-Methyl-3-pyrrolidinol
CAS:
688736-94-9
MF:
C5H11NO
Structure:
Chemical Name:
tert-butyl N-methyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl]carbamate
CAS:
1572399-64-4
MF:
C18H32BNO4
Structure:
Chemical Name:
ethyl 5-chloro-6-fluoropyrazolo[1,5-a]pyrimidine-3-carboxylate
CAS:
2359650-50-1
MF:
C9H7ClFN3O2
Chemical Name:
4-bromo-3-cyclohexyl-1-isopropyl-1H-pyrazole
Structure:
Chemical Name:
2,4-dichloro-7-fluoropyrido[3,2-d]pyrimidine
CAS:
1824318-03-7
MF:
C7H2Cl2FN3
Structure:
Chemical Name:
6-(2,2-Difluoropropyl)thieno[2,3-d]pyrimidin-4(3H)-one
CAS:
2163772-41-4
MF:
C9H8F2N2OS
Structure:
Chemical Name:
4-Chloro-6-methyl-2-(2,2,2-trifluoroethyl)-2H-pyrazolo[3,4-d]pyrimidine
CAS:
2163771-92-2
MF:
C8H6ClF3N4
Structure:
Chemical Name:
2-Amino-5-(trifluoromethyl)thieno[2,3-d]pyrimidin-4(1H)-one
CAS:
1423165-37-0
MF:
C7H4F3N3OS
Structure:
Chemical Name:
1-(4-METHYLBENZYL)-1H-BENZIMIDAZOLE-2-CARBALDEHYDE
CAS:
537010-30-3
MF:
C16H14N2O
Structure:
Chemical Name:
2-(2-HYDROXYPHENYL)BENZOXAZOLE
CAS:
835-64-3
MF:
C13H9NO2
Chemical Name:
2-(2,6-dioxopiperidin-3-yl)-5-(3-(hydroxymethyl)pyrrolidin-1-yl)isoindoline-1,3-dione
Structure:
Chemical Name:
2-(1-TRITYL-1H-IMIDAZOL-4-YL)-ETHYLAMINE HYDRATE
CAS:
195053-92-0
MF:
C24H23N3
Structure:
Chemical Name:
8-METHYL-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID
CAS:
88751-05-7
MF:
C9H8N2O2
Structure:
Chemical Name:
2,2'-Bioxazole, 4,4'-bis(4-fluorophenyl)-4,4',5,5'-tetrahydro-, (4S,4'S)-
CAS:
2567867-99-4
MF:
C18H14F2N2O2
Structure:
Chemical Name:
1-(4-BROMOBENZYL)-1H-IMIDAZOLE
CAS:
72459-46-2
MF:
C10H9BrN2
Chemical Name:
NA
CAS:
568591-00-4
Structure:
Chemical Name:
Tolytriazole sodium salt
CAS:
64665-57-2
MF:
C7H6N3Na
Structure:
Chemical Name:
1-(4-Nitrobenzyl)-1H-imidazole
CAS:
18994-90-6
MF:
C10H9N3O2
Structure:
Chemical Name:
(2-METHYLIMIDAZO[1,2-A]PYRIDIN-3-YL)METHANOL
CAS:
30489-44-2
MF:
C9H10N2O
Structure:
Chemical Name:
ETHYL IMIDAZO[2,1-B][1,3]BENZOTHIAZOLE-2-CARBOXYLATE
CAS:
64951-05-9
MF:
C12H10N2O2S
Structure:
Chemical Name:
BENZOTRIAZOLE, SODIUM SALT
CAS:
15217-42-2
MF:
C6H6N3Na
Structure:
Chemical Name:
8-NITROIMIDAZO[1,2-A]PYRIDINE
CAS:
52310-46-0
MF:
C7H5N3O2
Structure:
Chemical Name:
2,5-Dimethoxytetrahydrofuran
CAS:
696-59-3
MF:
C6H12O3
Structure:
Chemical Name:
6-METHYL-3H-BENZOTHIAZOL-2-ONE
CAS:
53827-53-5
MF:
C8H7NOS
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
Chemical Name:
6-amino-1-((2S,4R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxypyrrolidin-1-yl)hexan-1-one
Structure:
Chemical Name:
5H-indeno[1,2-b]pyridine
CAS:
244-99-5
MF:
C12H9N
Structure:
Chemical Name:
N,N-dimethylthio-2-thioxoimidazolidine-1-carboxamide
CAS:
935-75-1
MF:
C6H11N3OS3
Structure:
Chemical Name:
2-(pyrrolidinyl)pyrimidin-4-amine
CAS:
33851-99-9
MF:
C8H12N4
Structure:
Chemical Name:
2,5-Bis(octyldithio)-1,3,4-thiadiazole
CAS:
13539-13-4
MF:
C18H34N2S5
Structure:
Chemical Name:
4,5-dihydro-2-vinyl-1H-imidazole
CAS:
10577-96-5
MF:
C5H8N2
Structure:
Chemical Name:
4-(2,5-dibutoxy-4-nitrophenyl)morpholine
CAS:
86-15-7
MF:
C18H28N2O5
Structure:
Chemical Name:
2,6-Pyridinedicarboxamide, N2,N6-bis[(diethylamino)thioxomethyl]-
CAS:
320408-75-1
MF:
C17H25N5O2S2
Structure:
Chemical Name:
4,4,4',4',5,5,5',5'-octaethyl-2,2'-bi(1,3,2-dioxaborolane)
CAS:
2247367-07-1
MF:
C20H40B2O4
Structure:
Chemical Name:
L-Proline, 1-(2-naphthalenylacetyl)- (9CI)
CAS:
130654-11-4
MF:
C17H17NO3
Structure:
Chemical Name:
3H-Imidazo[4,5-c]pyridine-3,5,6(4H)-tricarboxylic acid, 6,7-dihydro-, 3,5-bis(1,1-dimethylethyl) ester, (6S)-
CAS:
1415602-89-9
MF:
C17H25N3O6
Structure:
Chemical Name:
Pyrimidine, 5-bromo-4-(difluoromethyl)-
CAS:
1780524-96-0
MF:
C5H3BrF2N2
Structure:
Chemical Name:
5-isopropyluracil
CAS:
17432-95-0
MF:
C7H10N2O2
Structure:
Chemical Name:
5-isopropyluracil
CAS:
17432-95-0
MF:
C7H10N2O2
Structure:
Chemical Name:
5-isopropyluracil
CAS:
17432-95-0
MF:
C7H10N2O2
Structure:
Chemical Name:
Piperazine, 1-(bromoacetyl)-4-methyl- (9CI)
CAS:
112257-15-5
MF:
C7H13BrN2O
Structure:
Chemical Name:
Pyridine, 4-ethyl-3-fluoro- (9CI)
CAS:
137234-73-2
MF:
C7H8FN
Chemical Name:
(2R,4R)-4-fluoro-2-methylpyrrolidine
Structure:
Chemical Name:
Formamide, N-1H-benzimidazol-4-yl- (9CI)
CAS:
137654-47-8
MF:
C8H7N3O
Structure:
Chemical Name:
(2S,4S)-4-fluoro-2-methylpyrrolidine hydrochloride
CAS:
2828444-34-2
MF:
C5H11ClFN
Structure:
Chemical Name:
2-pyridin-2-ylpyrimidine-5-carboxylic acid
CAS:
933988-22-8
MF:
C10H7N3O2
Structure:
Chemical Name:
Pyrimidine, 5-(bromomethyl)-2-(trifluoromethyl)- (9CI)
CAS:
198404-35-2
MF:
C6H4BrF3N2
Structure:
Chemical Name:
2,5-Dimethyl-1H-imidazole-4-carboxaldehyde
CAS:
68282-52-0
MF:
C6H8N2O
Structure:
Chemical Name:
2-triisopropylsilyl oxazole
CAS:
433332-27-5
MF:
C12H23NOSi
Structure:
Chemical Name:
Domazoline
CAS:
6043-01-2
MF:
C14H20N2O2
Structure:
Chemical Name:
9-phenyl-1,7-diazabicyclo[4.3.0]nona-2,4,6,8-tetraene
CAS:
92961-15-4
MF:
C13H10N2
Structure:
Chemical Name:
1,1'-bis(4-cyanophenyl)-[4,4'-bipyridine]-1,1'-diium chloride
CAS:
31515-20-5
MF:
C24H16ClN4+
Structure:
Chemical Name:
6-AMino-1-isobutyl-3-Methyl-5-nitroso-2,4-pyriMidinedione
CAS:
54052-67-4
MF:
C9H14N4O3
Structure:
Chemical Name:
tetrahydro-4-hydroxy-6-isopropyl-5,5-dimethyl-1H-pyrimidin-2-one
CAS:
14068-64-5
MF:
C9H18N2O2
Structure:
Chemical Name:
methyl (S)-2,5-dioxooxazolidine-4-propionate
CAS:
1663-47-4
MF:
C7H9NO5
Structure:
Chemical Name:
4-[2-(methylthio)ethyl]oxazolidine-2,5-dione
CAS:
5840-77-7
MF:
C6H9NO3S
Structure:
Chemical Name:
3-pyrrolidin-1-ylandrosta-3,5-dien-17-one
CAS:
905-30-6
MF:
C23H33NO
Structure:
Chemical Name:
3-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,5-a]pyrazine-1-carboxylic acid hydrochloride
CAS:
2172053-56-2
MF:
C8H9ClF3N3O2
Structure:
Chemical Name:
tetrahydro-1,3-bis(hydroxymethyl)-1H-pyrimidin-2-one
CAS:
3270-74-4
MF:
C6H12N2O3
Structure:
Chemical Name:
4-ethyl-2-methyl-4,5-dihydrothiazole
CAS:
4293-61-2
MF:
C6H11NS
Structure:
Chemical Name:
[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl] hydrogen succinate
CAS:
13182-87-1
MF:
C10H13N3O6
Structure:
Chemical Name:
(S)-2-(Methoxydiphenylmethyl)pyrrolidine
CAS:
118971-03-2
MF:
C18H21NO
Chemical Name:
1-(azetidin-3-yl)-4-iodo-1H-pyrazole hydrochloride
Structure:
Chemical Name:
(S)-4-iodo-1-(pyrrolidin-3-yl)-1H-pyrazole hydrochloride
CAS:
2828444-29-5
MF:
C7H11ClIN3
Structure:
Chemical Name:
2-Pyridinecarboxamide, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]amino]-1,2,5,6-tetrahydro-4-methyl-, (2S,5R)-
CAS:
2209874-05-3
MF:
C13H27N3O2Si
Structure:
Chemical Name:
1-methyl-2-Pyrrolidonium tetrafluoroborate chloride
CAS:
942068-29-3
MF:
C9H13N5
Structure:
Chemical Name:
Imidazo[1,2-a]pyrazine, 5,6,7,8-tetrahydro-2-(trifluoromethyl)- (9CI)
CAS:
126069-70-3
MF:
C7H8F3N3
Structure:
Chemical Name:
Proline, 1-(2-cyanoethyl)- (9CI)
CAS:
36901-89-0
MF:
C8H12N2O2
Structure:
Chemical Name:
Carbamic acid, [(3R,4S)-4-fluoro-3-pyrrolidinyl]-, 1,1-dimethylethyl ester, rel-
CAS:
169750-42-9
MF:
C9H17FN2O2
Structure:
Chemical Name:
1-Octanoylbenzotriazole
CAS:
58068-80-7
MF:
C14H19N3O
Structure:
Chemical Name:
3-(TRIFLUOROMETHYL)-5-P-TOLYL-1H-PYRAZOLE
CAS:
26974-15-2
MF:
C11H9F3N2
Structure:
Chemical Name:
5-Methyl-5-veratrylhydantoin
CAS:
892-02-4
MF:
C13H16N2O4
Structure:
Chemical Name:
QUINAZOLINE, 4-CHLORO-6-FLUORO-2-(TRIFLUOROMETHYL)-
CAS:
959238-11-0
MF:
C9H3ClF4N2
Structure:
Chemical Name:
1-benzoylpyrrolidin-2-one
CAS:
2399-66-8
MF:
C11H11NO2
Structure:
Chemical Name:
4,6-DICHLORO-2-PYRROLIDIN-1-YL-PYRIMIDINE
CAS:
154117-91-6
MF:
C8H9Cl2N3
Structure:
Chemical Name:
3-(1-methylethyl)-pyrazole
CAS:
49633-25-2
MF:
C6H10N2
Structure:
Chemical Name:
1-(3S)-3-Pyrrolidinyl-piperidine
CAS:
917560-78-2
MF:
C9H18N2
Structure:
Chemical Name:
2-bromo-5-phenyl-1,3-oxazole
CAS:
129053-70-9
MF:
C9H6BrNO
Structure:
Chemical Name:
3-Aminopyrrolidin-2-one hydrochloride
CAS:
117879-49-9
MF:
C4H8N2O.ClH
Structure:
Chemical Name:
2,5-Diphenylfuran
CAS:
955-83-9
MF:
C16H12O
Structure:
Chemical Name:
5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carbonitrile
CAS:
43024-16-4
MF:
C9H8N4
Structure:
Chemical Name:
5-Chlorobenzo[b]phosphindole
CAS:
33300-85-5
MF:
C12H8ClP
Structure:
Chemical Name:
5-CHLORO (1H)INDAZOLE
CAS:
698-26-0
MF:
C7H5ClN2
Structure:
Chemical Name:
5-bromo-6-chloro-1H-pyrazolo[3,4-b]pyridine
CAS:
1784380-03-5
MF:
C6H3BrClN3
Structure:
Chemical Name:
3-Hydroxymethylpyrrolidine
CAS:
5082-74-6
MF:
C5H11NO
Structure:
Chemical Name:
(1S,2S)-1,2-diphenyl-1-Pyrrolidineethanamine
CAS:
1416133-22-6
MF:
C18H22N2
Structure:
Chemical Name:
(R)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE
CAS:
110199-17-2
MF:
C10H11NS2
Structure:
Chemical Name:
cis-1-(tert-butoxycarbonyl)-4-ethylpyrrolidine-3-carboxylic acid
CAS:
1310731-87-3
MF:
C12H21NO4
Structure:
Chemical Name:
1,5-Diazabicyclo[4.3.0]non-5-ene
CAS:
3001-72-7
MF:
C7H12N2
Structure:
Chemical Name:
THYMINE-METHYL-D3-6-D
CAS:
156054-85-2
MF:
C5H2D4N2O2
Chemical Name:
5,5'-(5-aminopyrimidine-4,6-diyl)diisophthalic acid
CAS:
1980832-02-7
MF:
C20H13N3O8
Chemical Name:
1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl-2,2,3,3-d4)-2-(octylamino)-3-(pyrrolidin-1-yl)propan-1-ol
Structure:
Chemical Name:
4,4'-bis(4-methyl-1H-imidazol-1-yl)-1,1'-biphenyl
CAS:
1789726-52-8
MF:
C20H18N4
Structure:
Chemical Name:
1H-Imidazole-2-carboxylic acid, 1-(1-methylethyl)-, ethyl ester
CAS:
2017188-77-9
MF:
C9H14N2O2
Structure:
Chemical Name:
Ethanol, 2-[[(3aR,4S,6R,6aS)-6-[7-[[(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]amino]-5-(propylsulfonyl)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-
CAS:
1863036-51-4
MF:
C26H32F2N6O6S
Structure:
Chemical Name:
Pyrrolidine, 3-(4-chlorophenyl)-3-methyl-
CAS:
1250837-90-1
MF:
C11H14ClN
Structure:
Chemical Name:
4-CHLORO-2-HYDROXYQUINOLINE
CAS:
20146-59-2
MF:
C9H6ClNO