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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
OXOTREMORINE SESQUIFUMARATE OXOTREMORINE SESQUIFUMARATE 17360-35-9 C36H48N4O14
2,4,4-TRIMETHYL-2-OXAZOLINE 2,4,4-TRIMETHYL-2-OXAZOLINE 1772-43-6 C6H11NO
4-Thiazolecarboxylic acid 4-Thiazolecarboxylic acid 3973-08-8 C4H3NO2S
2-ISOPROPYL-4(5)-NITROIMIDAZOLE 2-ISOPROPYL-4(5)-NITROIMIDAZOLE 13373-32-5 C6H9N3O2
(2R,4S)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-((S)-1-(4-(4-methylthiazol-5-yl)phenyl)ethyl)pyrrolidine-2-carboxamide hydrochloride (2R,4S)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-((S)-1-(4-(4-methylthiazol-5-yl)phenyl)ethyl)pyrrolidine-2-carboxamide hydrochloride
2H-IMIDAZO[4,5-B]PYRAZIN-2-ONE, 1,3-DIHYDRO- 2H-IMIDAZO[4,5-B]PYRAZIN-2-ONE, 1,3-DIHYDRO- 16328-63-5 C5H4N4O
6-METHYL-2-(PIPERIDIN-4-YL)-1H-BENZO[D]IMIDAZOLE 6-METHYL-2-(PIPERIDIN-4-YL)-1H-BENZO[D]IMIDAZOLE 295790-48-6 C13H17N3
1,6-Diazabicyclo[3.2.1]octane-2-carboxylic acid, 7-oxo-6-(sulfooxy)-, 2-[2-[(3S)-3-pyrrolidinylcarbonyl]hydrazide], (1R,2S,5R)- 1,6-Diazabicyclo[3.2.1]octane-2-carboxylic acid, 7-oxo-6-(sulfooxy)-, 2-[2-[(3S)-3-pyrrolidinylcarbonyl]hydrazide], (1R,2S,5R)- 1452460-79-5 C12H19N5O7S
1-METHYL-1H-BENZOIMIDAZOL-5-YLAMINE TRIHYDROCHLORIDE 1-METHYL-1H-BENZOIMIDAZOL-5-YLAMINE TRIHYDROCHLORIDE 10394-38-4 C8H9N3
2,4(1H,3H)-Pyrimidinedione, 1-cyclopentyl- 2,4(1H,3H)-Pyrimidinedione, 1-cyclopentyl- 13345-72-7 C9H12N2O2
6-bromo-5-methyl-1H-imidazo[4,5-b]pyridine 6-bromo-5-methyl-1H-imidazo[4,5-b]pyridine 28279-41-6 C7H6BrN3
(-)-Menthyl (+)-2-pyrrolidone-5-carboxylate (-)-Menthyl (+)-2-pyrrolidone-5-carboxylate 68127-22-0 C15H25NO3
N-(6-amino-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-5-pyrimidinyl)formamide N-(6-amino-1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-5-pyrimidinyl)formamide 14785-95-6 C6H8N4O3
2,4,5-trimethylpyridine 2,4,5-trimethylpyridine 1122-39-0 C8H11N
4-methyloxazole 4-methyloxazole 693-93-6 C4H5NO
2-Aminobenzothiazole-6-carboxylic acid 2-Aminobenzothiazole-6-carboxylic acid 93-85-6 C8H6N2O2S
(S,R,S)-AHPC-PEG2-acid (S,R,S)-AHPC-PEG2-acid 2172820-09-4 C30H42N4O8S
ethyl 7-[(2R)-2-(hydroxymethyl)-5-oxo-1-pyrrolidinyl]heptanoate ethyl 7-[(2R)-2-(hydroxymethyl)-5-oxo-1-pyrrolidinyl]heptanoate 346672-97-7 C14H25NO4
Urea, N-[(3S,4R)-4-(3-fluorophenyl)-1-(2-methoxyethyl)-3-pyrrolidinyl]-N'-[4-methyl-3-(2-methyl-5-pyrimidinyl)-1-phenyl-1H-pyrazol-5-yl]- Urea, N-[(3S,4R)-4-(3-fluorophenyl)-1-(2-methoxyethyl)-3-pyrrolidinyl]-N'-[4-methyl-3-(2-methyl-5-pyrimidinyl)-1-phenyl-1H-pyrazol-5-yl]- 1824664-89-2 C29H32FN7O2
(S)-5-methyl-2-(pyrrolidin-2-yl)pyridine (S)-5-methyl-2-(pyrrolidin-2-yl)pyridine 1213645-44-3 C10H14N2
(S)-ALPHA,ALPHA-BIS(4-METHOXYPHENYL)-2-PYRROLIDINEMETHANOL (S)-ALPHA,ALPHA-BIS(4-METHOXYPHENYL)-2-PYRROLIDINEMETHANOL 131180-57-9 C19H23NO3
3,5,6-Trichloro-1,2,4-triazine 3,5,6-Trichloro-1,2,4-triazine 873-41-6 C3Cl3N3
5-(Hydroxymethyl)-1-methyl-1H-pyrazole 5-(Hydroxymethyl)-1-methyl-1H-pyrazole 84547-61-5 C5H8N2O
Dimethylmethoxy chromanol Dimethylmethoxy chromanol 83923-51-7 C12H16O3
2,2'-Bi-1H-imidazole, 4,4',5,5'-tetrahydro-4,4'-bis(1-methylethyl)-1,1'-bis(3-methylphenyl)-, (4S,4'S)- 2,2'-Bi-1H-imidazole, 4,4',5,5'-tetrahydro-4,4'-bis(1-methylethyl)-1,1'-bis(3-methylphenyl)-, (4S,4'S)- 2374958-85-5 C26H34N4
Pyrrolidine, 4-fluoro-2-methyl-, hydrochloride (1:1), (2R,4R)- Pyrrolidine, 4-fluoro-2-methyl-, hydrochloride (1:1), (2R,4R)- 2300174-87-0 C5H11ClFN
6-BROMO-2,4-DICHLOROQUINAZOLINE 6-BROMO-2,4-DICHLOROQUINAZOLINE 102393-82-8 C8H3BrCl2N2
Imidazo[1,2-a]pyridine-2-carboxaldehyde, 8-methyl- (9CI) Imidazo[1,2-a]pyridine-2-carboxaldehyde, 8-methyl- (9CI) 143982-39-2 C9H8N2O
Quinazoline, 4-methyl- (6CI,7CI,8CI,9CI) Quinazoline, 4-methyl- (6CI,7CI,8CI,9CI) 700-46-9 C9H8N2
3-Pyrrolidinol, 3-[(3-bromo-5-fluorophenyl)methyl]- 3-Pyrrolidinol, 3-[(3-bromo-5-fluorophenyl)methyl]- 1515119-28-4 C11H13BrFNO
1-Propanone, 1-(2-pyrimidinyl)- (9CI) 1-Propanone, 1-(2-pyrimidinyl)- (9CI) 54643-09-3 C7H8N2O
2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)- (9CI) 2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)- (9CI) 274901-37-0 C7H9ClN2O
1-(3,4-dimethyl-1H-pyrazol-1-yl)ethan-1-one 1-(3,4-dimethyl-1H-pyrazol-1-yl)ethan-1-one 856064-45-4 C7H10N2O
Sodium benzotriazole Sodium benzotriazole
Pyrrolidinone, dimethyl- Pyrrolidinone, dimethyl- 60544-40-3
4(5)-CYANOMETHYLIMIDAZOLE 4(5)-CYANOMETHYLIMIDAZOLE 18502-05-1 C5H5N3
1H-1,2,3-TRIAZOLE, 4-BROMO-1-METHYL- 1H-1,2,3-TRIAZOLE, 4-BROMO-1-METHYL- 13273-53-5 C3H4BrN3
3-CYCLOPENTYLACRYLONITRILE 3-CYCLOPENTYLACRYLONITRILE 591769-05-0 C8H11N
4-METHYL-1H-1,2,3-TRIAZOLE 4-METHYL-1H-1,2,3-TRIAZOLE 27808-16-8 C3H5N3
4-Amino-8-bromo-2-chloroquinazoline 4-Amino-8-bromo-2-chloroquinazoline 956100-62-2 C8H5BrClN3
Ethyl 3-amino-6-(trifluoromethyl)imidazo-[1,2-a]pyridine-2-carboxylate Ethyl 3-amino-6-(trifluoromethyl)imidazo-[1,2-a]pyridine-2-carboxylate 1171919-18-8 C11H10F3N3O2
4,5-Dichloro-1H-pyrrolo[2,3-b]pyridine 4,5-Dichloro-1H-pyrrolo[2,3-b]pyridine 1142192-58-2 C7H4Cl2N2
4-[(4-Chlorophenyl)-2-pyridinylmethoxy]-1-piperidinecarboxylic acid ethyl ester 4-[(4-Chlorophenyl)-2-pyridinylmethoxy]-1-piperidinecarboxylic acid ethyl ester 207726-35-0 C20H23ClN2O3
(2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine (2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine 483366-12-7 C10H16N2O3
3-Cyano-4-methylphenylboronic acid, pinacol ester 3-Cyano-4-methylphenylboronic acid, pinacol ester 1220219-11-3 C14H18BNO2
(S)-tert-butyl 2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate (S)-tert-butyl 2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate 1007882-58-7 C12H19N3O2
4-bromooxazole 4-bromooxazole 1240598-57-5 C3H2BrNO
(S)-2-[(Diphenylphosphino)methyl]pyrrolidine, min. 97% (S)-2-[(Diphenylphosphino)methyl]pyrrolidine, min. 97% 60261-46-3 C17H20NP
7-chloro-2-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one(SALTDATA: FREE) 7-chloro-2-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one(SALTDATA: FREE) 162469-87-6 C9H6Cl2N2O
1,3-Dicyclohexylbenzimidazolium chloride, min. 97% 1,3-Dicyclohexylbenzimidazolium chloride, min. 97% 1034449-15-4 C19H27ClN2
3-cyclopropyl-1H-1,2,4-triazole(SALTDATA: FREE) 3-cyclopropyl-1H-1,2,4-triazole(SALTDATA: FREE) 1211390-33-8 C5H7N3
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 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 268545-13-7 C21H24FN3O4
5-Ethyl-3-(pyrrolidin-3-ylmethoxymethyl)-[1,2,4]oxadiazole 5-Ethyl-3-(pyrrolidin-3-ylmethoxymethyl)-[1,2,4]oxadiazole 914299-45-9 C10H17N3O2
Pyrrolidine, 2-(2-hydrazinylethyl)-1-methyl-, hydrochloride (1:1) Pyrrolidine, 2-(2-hydrazinylethyl)-1-methyl-, hydrochloride (1:1) 1269292-40-1 C7H18ClN3
7-Bromo-1-methyl-1H-indole 97% 7-Bromo-1-methyl-1H-indole 97% 280752-68-3 C9H8BrN
7H-Pyrrolo[1,2-a]imidazol-7-one,5,6-dihydro-(9CI) 7H-Pyrrolo[1,2-a]imidazol-7-one,5,6-dihydro-(9CI) 112513-82-3 C6H6N2O
3-Pyrrolidinamine,4-fluoro-,dihydrochloride,trans-(9CI) 3-Pyrrolidinamine,4-fluoro-,dihydrochloride,trans-(9CI) 125197-40-2 C4H9FN2.2ClH
1H-Benzimidazole,2-ethenyl-(9CI) 1H-Benzimidazole,2-ethenyl-(9CI) 14984-26-0 C9H8N2
2H-Imidazo[4,5-b]pyridin-2-one,5-amino-1,3-dihydro-(9CI) 2H-Imidazo[4,5-b]pyridin-2-one,5-amino-1,3-dihydro-(9CI) 40851-87-4 C6H6N4O
1,2,4-triazole potassium salt 1,2,4-triazole potassium salt C2H2KN3
1-(diethoxyMethyl)-4,5-diMethyl-1H-iMidazole 1-(diethoxyMethyl)-4,5-diMethyl-1H-iMidazole 74483-00-4 C10H18N2O2
1-(Phenylsulfonyl)-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine 1-(Phenylsulfonyl)-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-c]pyridine 1174038-65-3 C19H21BN2O4S
1,3-diMethyliMidazoliuM dicyanaMide 1,3-diMethyliMidazoliuM dicyanaMide 869301-19-9 C7H9N5
1-tert-Butyl-1H-pyrazole 1-tert-Butyl-1H-pyrazole 15754-60-6 C7H12N2
1-(3-Methoxypropyl)-4-piperidinamine 1-(3-Methoxypropyl)-4-piperidinamine 179474-79-4 C9H20N2O
1-tert-butyl-3-phenyl-1H-pyrazole 1-tert-butyl-3-phenyl-1H-pyrazole 1269293-29-9 C13H16N2
1H-Pyrazolo[4,3-b]pyridine-6-carboxylicacid 1H-Pyrazolo[4,3-b]pyridine-6-carboxylicacid 1256807-59-6 C7H5N3O2
2-broMo-5-Methyl-oxazole 2-broMo-5-Methyl-oxazole 129053-67-4 C4H4BrNO
IMidazo[1,2-a]pyridin-8-aMine, 5-broMo- IMidazo[1,2-a]pyridin-8-aMine, 5-broMo- 1357947-00-2 C7H6BrN3
IMidazo[1,2-a]pyridine-2-carboxylic acid, 7-chloro- IMidazo[1,2-a]pyridine-2-carboxylic acid, 7-chloro- 1020038-42-9 C8H5ClN2O2
4-chloro-2-fluoro-5-iodopyridine 4-chloro-2-fluoro-5-iodopyridine 1184914-20-2 C5H2ClFIN
(S)-N-(Pyrrolidin-3-yl)acetaMide hydrochloride (S)-N-(Pyrrolidin-3-yl)acetaMide hydrochloride 1246277-44-0 C6H13ClN2O
3-fluoro-4-(4-Methyl-1H-iMidazol-1-yl)benzoic acid 3-fluoro-4-(4-Methyl-1H-iMidazol-1-yl)benzoic acid 1243205-04-0 C11H9FN2O2
3-(1-chloroH-pyrrolo[1,2-a]pyrazin-6-yl)cyclobutanone 3-(1-chloroH-pyrrolo[1,2-a]pyrazin-6-yl)cyclobutanone 936901-72-3 C10H8ClN3O
N-Cyclopropyl-3-oxetanamine N-Cyclopropyl-3-oxetanamine 1340518-89-9 C6H11NO
8-BroMo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine 8-BroMo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine 643067-83-8 C7H6BrNO2
2-Ethyl-2-oxazoline 2-Ethyl-2-oxazoline 10431-98-8 C5H9NO
1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]iMidazol-2(3H)-one 1-Methyl-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]iMidazol-2(3H)-one 1187968-73-5 C14H19BN2O3
8-BroMo-3-iodo-iMidazo[1,2-a]pyridine 8-BroMo-3-iodo-iMidazo[1,2-a]pyridine 1232038-69-5 C7H4BrIN2
N-(4-Nitrophenyl)-4-(3-pyridyl)-2-pyriMidineaMine N-(4-Nitrophenyl)-4-(3-pyridyl)-2-pyriMidineaMine 181065-58-7 C15H11N5O2
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 C20H27FN2O3
1,2,4-Triazolylsodium 1,2,4-Triazolylsodium 41253-21-8 C2H4N3Na
4-(4-(Trifluoromethoxy)phenyl)piperidine 4-(4-(Trifluoromethoxy)phenyl)piperidine 180160-91-2 C12H14F3NO
Pyridine,2,2'-(1,3-phenylene)bis- Pyridine,2,2'-(1,3-phenylene)bis- 136538-84-6 C16H12N2
1(tertbutoxycarbonyl)4,4difluoropyrrolidine3carboxylic acid 1(tertbutoxycarbonyl)4,4difluoropyrrolidine3carboxylic acid 1196145-11-5 C10H15F2NO4
2,6-Bis[(4R)-benzyl-2-oxazolin-2-yl]pyridine 2,6-Bis[(4R)-benzyl-2-oxazolin-2-yl]pyridine 365215-38-9 C25H23N3O2
5-BroMo-2-chloro-thiazolo[5,4-b]pyridine 5-BroMo-2-chloro-thiazolo[5,4-b]pyridine 1355241-50-7 C6H2BrClN2S
propan-2-one compound with imidazo[1,2-a]pyridine (1:1) propan-2-one compound with imidazo[1,2-a]pyridine (1:1) 116355-08-9 C10H10N2O
5-AMino-2-chloropyriMidine-4-carboxaMide 5-AMino-2-chloropyriMidine-4-carboxaMide 189747-29-3 C5H5ClN4O
5-METHYL-1,2,4-OXADIAZOL-3-AMINE 5-METHYL-1,2,4-OXADIAZOL-3-AMINE 40483-47-4 C3H5N3O
5-Bromo-1H-benzimidazole 5-Bromo-1H-benzimidazole 4887-88-1 C7H5BrN2
4-(CHLOROMETHYL)-1-TRITYL-1H-IMIDAZOLE 4-(CHLOROMETHYL)-1-TRITYL-1H-IMIDAZOLE 103057-10-9 C23H19ClN2
BTL benzotriazole BTL benzotriazole
Benzotriazole derivative Benzotriazole derivative
3-bromo-1-(oxan-2-yl)-1h-pyrazole 3-bromo-1-(oxan-2-yl)-1h-pyrazole 1044270-96-3 C8H11BrN2O
6-Bromo-8-methyl-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester 6-Bromo-8-methyl-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester 907945-82-8 C11H11BrN2O2
alpha-Glucosyl Hesperidin alpha-Glucosyl Hesperidin 161713-86-6 C34H44O20
3-[1-(4-Amino-butyl)-1H-[1,2,3]triazol-4-yl]-phenylamine 3-[1-(4-Amino-butyl)-1H-[1,2,3]triazol-4-yl]-phenylamine 1626413-52-2 C12H17N5
5-bromo-4-methylnicotinonitrile 5-bromo-4-methylnicotinonitrile 890092-52-1 C7H5BrN2
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