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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
5-(Trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid 5-(Trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid 1260798-62-6 C9H5F3N2O2
4-(morpholin-4-yl-phenoxy-phosphoryl)morpholine 4-(morpholin-4-yl-phenoxy-phosphoryl)morpholine 4881-17-8 C14H21N2O4P
2-Mercaptobenzoxazole 2-Mercaptobenzoxazole 2382-96-9 C7H5NOS
2-(METHYLTHIO)-2-IMIDAZOLINE 2-(METHYLTHIO)-2-IMIDAZOLINE 20112-79-2 C4H8N2S
3,4-Epoxytetrahydrofuran 3,4-Epoxytetrahydrofuran 285-69-8 C4H6O2
7-METHYL-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 7-METHYL-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 80353-94-2 C9H8N2O2
2-METHYL-3-(4-SULFOBUTYL)BENZOXAZOLIUM BETAINE 2-METHYL-3-(4-SULFOBUTYL)BENZOXAZOLIUM BETAINE 112339-60-3 C12H15NO4S
8-METHYL-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER 8-METHYL-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER 67625-40-5 C11H12N2O2
1-Ethylpyrazole 1-Ethylpyrazole 2817-71-2 C5H8N2
3-(3,5-di-pyridin-4-yl-(1,2,4)triazol-1-ylmethyl)-pyridine 3-(3,5-di-pyridin-4-yl-(1,2,4)triazol-1-ylmethyl)-pyridine 55391-41-8 C18H14N6
5-fluoro-2-methoxy-3-(pyrrolidin-2-yl)pyridine 5-fluoro-2-methoxy-3-(pyrrolidin-2-yl)pyridine 1337444-35-5 C10H13FN2O
5-(Trifluoromethyl)-1H-1,2,3-triazole 5-(Trifluoromethyl)-1H-1,2,3-triazole 40964-54-3 C3H2F3N3
3-(4-Bromophenyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 3-(4-Bromophenyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 1255381-85-1 C16H9BrN2O2S
Isoxazole, 3-chloro-4,5-dihydro-5,5-dimethyl- Isoxazole, 3-chloro-4,5-dihydro-5,5-dimethyl- 326829-08-7 C5H8ClNO
(S)-5-AMINOMETHYL-PYRROLIDIN-2-ONE (S)-5-AMINOMETHYL-PYRROLIDIN-2-ONE 145414-31-9 C5H10N2O
2169919-97-3 2169919-97-3 2169919-97-3 C17H19ClFN3O2
(1H-BENZOIMIDAZOL-2-YL)-PHENYL-AMINE (1H-BENZOIMIDAZOL-2-YL)-PHENYL-AMINE 21578-58-5 C13H11N3
3-((S)-2-(cyclopent-1-en-1-yl)-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidin-1-ium bromide 3-((S)-2-(cyclopent-1-en-1-yl)-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidin-1-ium bromide C19H26BrNO3
2-(4-BROMOBENZYL)-1H-BENZIMIDAZOLE 2-(4-BROMOBENZYL)-1H-BENZIMIDAZOLE 100622-41-1 C14H11BrN2
4-Amino-2-chloro-6-methyl-5-nitropyrimidine ,98% 4-Amino-2-chloro-6-methyl-5-nitropyrimidine ,98% C5H5ClN4O2
2-Methylindole-3-ethylamine 2-Methylindole-3-ethylamine 2731-06-8 C11H14N2
(Diacetoxyiodo)benzene (Diacetoxyiodo)benzene 3240-34-4 C10H11IO4
(S)-2-(2-CHLOROPHENYL)PYRROLIDINE (S)-2-(2-CHLOROPHENYL)PYRROLIDINE 1217788-99-2 C10H12ClN
5-OXO-5-PYRROLIDIN-1-YL-PENTANOIC ACID 5-OXO-5-PYRROLIDIN-1-YL-PENTANOIC ACID 5724-80-1 C9H15NO3
Fluorodi(4-morpholinyl)phosphine oxide Fluorodi(4-morpholinyl)phosphine oxide 565-25-3 C8H16FN2O3P
5-AMINO-1,3-DIMETHYL-1,3-DIHYDRO-BENZOIMIDAZOL-2-ONE 5-AMINO-1,3-DIMETHYL-1,3-DIHYDRO-BENZOIMIDAZOL-2-ONE 53439-88-6 C9H11N3O
N-(4-PHENOXYPHENYL)PICOLINAMIDE N-(4-PHENOXYPHENYL)PICOLINAMIDE 255904-96-2 C18H14N2O2
4-METHOXY-1H-PYRAZOLO[3,4-D]PYRIMIDIN-6-AMINE 4-METHOXY-1H-PYRAZOLO[3,4-D]PYRIMIDIN-6-AMINE 100644-67-5 C6H7N5O
(S)-pyrrolidine-3-carboxylic acid hydrochloride (S)-pyrrolidine-3-carboxylic acid hydrochloride 1124369-40-9 C5H10ClNO2
4-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-d]pyrimidine 4-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-d]pyrimidine 876343-09-8 C12H7ClIN3O2S
2-ISOPROPYL PYRIDINE 2-ISOPROPYL PYRIDINE 644-98-4 C8H11N
7-Bromo-2-methylbenzo[d]oxazole 7-Bromo-2-methylbenzo[d]oxazole 1239489-82-7 C8H6BrNO
2-Trifluoromethylimidazole-4-carboxylic acid 2-Trifluoromethylimidazole-4-carboxylic acid 78016-98-5 C5H3F3N2O2
3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine 3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine 30169-25-6 C12H14N8
3-Ethyl-3-[(2-ethylhexyloxy)methyl]oxetane 3-Ethyl-3-[(2-ethylhexyloxy)methyl]oxetane 298695-60-0 C14H28O2
2-Oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride 2-Oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride 781649-84-1 C11H15ClN4O
6-Nitroimidazo[1,2-a]pyridine-2-carboxylic acid 6-Nitroimidazo[1,2-a]pyridine-2-carboxylic acid 904805-51-2 C8H5N3O4
5-hydroxy-pyrazole 5-hydroxy-pyrazole 60456-92-0 C3H4N2O
2,4-Dichloro-6-methylthieno[2,3-d]pyrimidine 2,4-Dichloro-6-methylthieno[2,3-d]pyrimidine 76872-23-6 C7H4Cl2N2S
4-broMo-2-(2-Methoxyethoxy)pyridine 4-broMo-2-(2-Methoxyethoxy)pyridine 1289131-55-0 C8H10BrNO2
1-tert-Butyl 2-methyl 2-methylpyrrolidine-1,2-dicarboxylate 1-tert-Butyl 2-methyl 2-methylpyrrolidine-1,2-dicarboxylate 317355-80-9 C12H21NO4
1H-Pyrazole-1-propanenitrile, β-cyclopentyl-4-[7-[[2-(triMethylsilyl)ethoxy]Methyl]-7H-pyrrolo[2,3-d]pyriMidin-4-yl]-, (βR)- 1H-Pyrazole-1-propanenitrile, β-cyclopentyl-4-[7-[[2-(triMethylsilyl)ethoxy]Methyl]-7H-pyrrolo[2,3-d]pyriMidin-4-yl]-, (βR)- 941685-40-1 C23H32N6OSi
5-Chloro-7-(trifluoromethyl)imidazo[1,5-a]pyridine 5-Chloro-7-(trifluoromethyl)imidazo[1,5-a]pyridine 2064217-73-6 C8H4ClF3N2
CIS-OCTAHYDRO-2H-BENZIMIDAZOL-2-ONE CIS-OCTAHYDRO-2H-BENZIMIDAZOL-2-ONE 1123-97-3 C7H12N2O
1-METHYL-1,5-DIHYDRO-4H-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE 1-METHYL-1,5-DIHYDRO-4H-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE 5334-56-5 C6H6N4O
4,5-Dichloro-1,2,3-dithiazolium chloride 4,5-Dichloro-1,2,3-dithiazolium chloride 75318-43-3 C2Cl3NS2
3-(2-methyl-6-methylthiophenyl)-4,5-dihydroisoxazole 3-(2-methyl-6-methylthiophenyl)-4,5-dihydroisoxazole 250592-91-7 C11H13NOS
1-Pentanone, 4-methyl-1-phenyl-2-(1-pyrrolidinyl)- 1-Pentanone, 4-methyl-1-phenyl-2-(1-pyrrolidinyl)- 2181620-71-1 C16H23NO
4-Aminofuro[3,2-d]pyrimidine-7-carboxylic acid 4-Aminofuro[3,2-d]pyrimidine-7-carboxylic acid 1206181-18-1 C7H5N3O3
4-Chloro-6-(2,2-difluoropropyl)thieno[2,3-d]pyrimidine 4-Chloro-6-(2,2-difluoropropyl)thieno[2,3-d]pyrimidine 2180956-71-0 C9H7ClF2N2S
2-(Bromomethyl)-6-methyl-2H-oxazolo[3,2-a]pyrimidin-7(3H)-one 2-(Bromomethyl)-6-methyl-2H-oxazolo[3,2-a]pyrimidin-7(3H)-one 315186-62-0 C8H9BrN2O2
(2,5-dioxopyrrolidin-1-yl) but-2-enoate (2,5-dioxopyrrolidin-1-yl) but-2-enoate 53665-20-6 C8H9NO4
(TRANS)-4-(4-CHLORO-PHENYL)-PYRROLIDINE-3-CARBOXYLIC ACID-HCL (TRANS)-4-(4-CHLORO-PHENYL)-PYRROLIDINE-3-CARBOXYLIC ACID-HCL 1807940-40-4 C11H13Cl2NO2
N,N'-BIS-BOC-1-GUANYLPYRAZOLE N,N'-BIS-BOC-1-GUANYLPYRAZOLE 152120-54-2 C14H22N4O4
2,4-DICHLORO-5-FLUORO-7H-PYRROLO[2,3-D]PYRIMIDINE 2,4-DICHLORO-5-FLUORO-7H-PYRROLO[2,3-D]PYRIMIDINE 1053228-29-7 C6H2Cl2FN3
3-BroMo-pyrrolidine hydrochloride 3-BroMo-pyrrolidine hydrochloride 952748-39-9 C4H9BrClN
5-bromo-4-fluoro-1H-indazole 5-bromo-4-fluoro-1H-indazole 1082041-85-7 C7H4BrFN2
Ethyl 7H-pyrrolo[2,3-d]pyriMidine-4-carboxylate Ethyl 7H-pyrrolo[2,3-d]pyriMidine-4-carboxylate 915142-91-5 C9H9N3O2
5-benzyl-4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridine 5-benzyl-4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridine 35005-72-2 C13H14N2O
3-diMethylpyrrolidine-3-carboxylic acid 3-diMethylpyrrolidine-3-carboxylic acid 912771-28-9 C7H13NO2
5-Bromoisoxazole 5-Bromoisoxazole 1133930-99-0 C3H2BrNO
6-(Trifluoromethyl)pyridine-2-carbonyl chloride 6-(Trifluoromethyl)pyridine-2-carbonyl chloride 1099597-77-9 C7H3ClF3NO
6-Bromo-3-nitro-pyrazolo[1,5-a]pyrimidine 6-Bromo-3-nitro-pyrazolo[1,5-a]pyrimidine 300361-77-7 C6H3BrN4O2
3-methyl-5-(pyrrolidin-3-yl)-1,2,4-oxadiazolidine 3-methyl-5-(pyrrolidin-3-yl)-1,2,4-oxadiazolidine 82268-15-3 C8H16O3
4-bromo-1-tert-butyl-1H-pyrazole 4-bromo-1-tert-butyl-1H-pyrazole 70951-85-8 C7H11BrN2
6-bromo-2-chloropyrimidin-4-amine 6-bromo-2-chloropyrimidin-4-amine 1333319-66-6 C4H3BrClN3
5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(2,2,2-trifluoroethoxy)pyrimidine 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(2,2,2-trifluoroethoxy)pyrimidine 1351234-12-2 C12H16BF3N2O3
4-(2-OXO-2-PYRROLIDIN-1-YL-ETHOXY)-BENZALDEHYDE 4-(2-OXO-2-PYRROLIDIN-1-YL-ETHOXY)-BENZALDEHYDE 438229-79-9 C13H15NO3
4-bromomethyloxazole 4-bromomethyloxazole 1065073-37-1 C4H4BrNO
2-bromo-5-pyrrolidin-1-ylpyrazine 2-bromo-5-pyrrolidin-1-ylpyrazine 1001050-21-0 C8H10BrN3
(R)-1-(1H-Benzimidazol-2-yl)-3-methylbutylamine Hydrochloride (R)-1-(1H-Benzimidazol-2-yl)-3-methylbutylamine Hydrochloride 1235643-62-5 C12H18ClN3
4-Thioxo-2-iMidazolidinone 4-Thioxo-2-iMidazolidinone 16310-60-4 C3H4N2OS
3,7-dibroModibenzo[b,d]furan 3,7-dibroModibenzo[b,d]furan 67019-91-4 C12H6Br2O
1-Boc-3-(aMinoMethyl)-3-hydroxypyrrolidine 1-Boc-3-(aMinoMethyl)-3-hydroxypyrrolidine 114214-73-2 C10H20N2O3
IMidazo[1,2-a]pyridine,6-Methoxy- IMidazo[1,2-a]pyridine,6-Methoxy- 955376-51-9 C8H8N2O
7-Methoxy-4-nitro-1H-pyrazolo[3,4-c]pyridine 7-Methoxy-4-nitro-1H-pyrazolo[3,4-c]pyridine 1416374-56-5 C7H6N4O3
(S)-1-(5-fluoropyriMidin-2-yl)ethanaMine hydrochloride (S)-1-(5-fluoropyriMidin-2-yl)ethanaMine hydrochloride 935667-21-3 C6H9ClFN3
4-BROMOBENZO[D]OXAZOLE 4-BROMOBENZO[D]OXAZOLE 217326-65-3 C7H4BrNO
ethyl 5-aMino-2,6-dichloropyriMidine-4-carboxylate ethyl 5-aMino-2,6-dichloropyriMidine-4-carboxylate 54368-62-6 C7H7Cl2N3O2
(2R)-2-ethynyl-Pyrrolidine (2R)-2-ethynyl-Pyrrolidine 128959-89-7 C6H9N
3-(trifluoroMethyl)-1H-Pyrazole-4-Methanol 3-(trifluoroMethyl)-1H-Pyrazole-4-Methanol 1001020-13-8 C5H5F3N2O
(2R,4R)-1-CBZ-4-aMino Pyrrolidine-2-carboxylic acid Methylester-HCl (2R,4R)-1-CBZ-4-aMino Pyrrolidine-2-carboxylic acid Methylester-HCl 1217457-41-4 C14H19ClN2O4
2-(benzo[d]thiazol-2-yl)-2-(2-chloropyriMidin-4-yl)acetonitrile 2-(benzo[d]thiazol-2-yl)-2-(2-chloropyriMidin-4-yl)acetonitrile 345986-38-1 C13H7ClN4S
6-Quinazolinecarbonitrile, 3,4-dihydro-4-oxo- 6-Quinazolinecarbonitrile, 3,4-dihydro-4-oxo- 117297-41-3 C9H5N3O
2,5-Dioxopyrrolidin-1-yl 6-((((9H-fluoren-9-yl)Methoxy)carbonyl)aMino)hexanoate 2,5-Dioxopyrrolidin-1-yl 6-((((9H-fluoren-9-yl)Methoxy)carbonyl)aMino)hexanoate 125697-63-4 C25H26N2O6
9-Methyl-9H-beta-carboline 9-Methyl-9H-beta-carboline 2521-07-5 C12H10N2
(1S,2S) 2-(1-pyrrolidinyl)-cyclohexanaMine (1S,2S) 2-(1-pyrrolidinyl)-cyclohexanaMine 824938-97-8 C10H20N2
4-broMo-1-(2-Methoxyethyl)-1H-pyrazole 4-broMo-1-(2-Methoxyethyl)-1H-pyrazole 847818-49-9 C6H9BrN2O
2-Methyl-4,5,6,7-tetrahydro-3H-iMidazo[4,5-c]pyridine hydrochloride 2-Methyl-4,5,6,7-tetrahydro-3H-iMidazo[4,5-c]pyridine hydrochloride 1159011-01-4 C7H12ClN3
Uridine, 4'-C-azido-5'-deoxy-5'-iodo-, 2',3'-dibenzoate Uridine, 4'-C-azido-5'-deoxy-5'-iodo-, 2',3'-dibenzoate 139419-02-6 C23H18IN5O7
2,4-dichloro-6-cyclopropyl-5,6,7,8-tetrahydropyrido[4,3-d]pyriMidine 2,4-dichloro-6-cyclopropyl-5,6,7,8-tetrahydropyrido[4,3-d]pyriMidine 1449117-31-0 C10H11Cl2N3
1-(difluoroMethyl)-4-iodo-1H-pyrazole 1-(difluoroMethyl)-4-iodo-1H-pyrazole 1041205-43-9 C4H3F2IN2
3,3-diMethyl-6-nitrobenzo[c][1,2]oxaborol-1(3H)-ol 3,3-diMethyl-6-nitrobenzo[c][1,2]oxaborol-1(3H)-ol 1266084-47-2 C9H10BNO4
1H-Pyrazole, 4,4'-(1,4-phenylene)bis[3,5-diMethyl- 1H-Pyrazole, 4,4'-(1,4-phenylene)bis[3,5-diMethyl- 14181-26-1 C16H18N4
5-BroMo-2-chloro-4-ethoxypyriMidine 5-BroMo-2-chloro-4-ethoxypyriMidine 1289005-72-6 C6H6BrClN2O
2-chloro-3-(MethoxyMethoxy)pyridine 2-chloro-3-(MethoxyMethoxy)pyridine 862667-72-9 C7H8ClNO2
(3S,5R)-5-Methylpyrrolidin-3-ol (3S,5R)-5-Methylpyrrolidin-3-ol 1108234-25-8 C5H11NO
7-(TrifluoroMethyl)iMidazo[1,2-a]pyridine-2-carboxylic acid 7-(TrifluoroMethyl)iMidazo[1,2-a]pyridine-2-carboxylic acid 1620569-19-8 C9H5F3N2O2
6-aMino-3-Methyl-1-(ethyl)-1,2,3,4-tetrahydropyriMidine-2,4-dione 6-aMino-3-Methyl-1-(ethyl)-1,2,3,4-tetrahydropyriMidine-2,4-dione 41862-13-9 C7H11N3O2
3-broMo-5-(trifluoroMethoxy)pyridine 3-broMo-5-(trifluoroMethoxy)pyridine 1060815-01-1 C6H3BrF3NO
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