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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
TERT-BUTYL 2-(6-BROMOPYRIDIN-3-YL)MORPHOLINE-4-CARBOXYLATE TERT-BUTYL 2-(6-BROMOPYRIDIN-3-YL)MORPHOLINE-4-CARBOXYLATE 1427502-18-8 C14H19BrN2O3
2-BROMO-5-PHENYL-4-PYRIDINAMINE 2-BROMO-5-PHENYL-4-PYRIDINAMINE 102249-55-8 C11H9BrN2
Methyl 2-oxindole-4-carboxylate Methyl 2-oxindole-4-carboxylate 90924-46-2 C10H9NO3
ETHYL 5-AMINO-1-(TERT-BUTYL)-1H-IMIDAZOLE-4-CARBOXYLATE ETHYL 5-AMINO-1-(TERT-BUTYL)-1H-IMIDAZOLE-4-CARBOXYLATE 76182-23-5 C10H17N3O2
2-CHLORO-4-BENZYLAMINO-5-METHYLPYRIMIDINE 2-CHLORO-4-BENZYLAMINO-5-METHYLPYRIMIDINE 91396-13-3 C12H12ClN3
6-pyridin-2-ylpyrimidin-4-ol 6-pyridin-2-ylpyrimidin-4-ol 1105195-55-8 C9H7N3O
6-Piperidin-4-yl-pyrimidin-4-ylamine 6-Piperidin-4-yl-pyrimidin-4-ylamine 1545673-46-8 C9H14N4
(R)-5-AMINOMETHYL-PYRROLIDIN-2-ONE (R)-5-AMINOMETHYL-PYRROLIDIN-2-ONE 173336-98-6 C5H10N2O
4-bromothieno[3,2-d]pyrimidine 4-bromothieno[3,2-d]pyrimidine 16285-70-4 C6H3BrN2S
5-bromo-3-methylpyridazine 5-bromo-3-methylpyridazine 1891259-97-4 C5H5BrN2
(S)-4,5-DIHYDRO-2-(2-((S)-4,5-DIHYDRO-4-ISOPROPYLOXAZOL-2-YL)PROPAN-2-YL)-4-ISOPROPYLOXAZOLE (S)-4,5-DIHYDRO-2-(2-((S)-4,5-DIHYDRO-4-ISOPROPYLOXAZOL-2-YL)PROPAN-2-YL)-4-ISOPROPYLOXAZOLE 131833-92-6 C15H26N2O2
2-Amino-4-(tetrahydropyran-4-yl)pyridine 2-Amino-4-(tetrahydropyran-4-yl)pyridine 1159818-13-9 C10H14N2O
6-Bromoisatin 6-Bromoisatin 6326-79-0 C8H4BrNO2
4-(4-bromo-1H-imidazol-1-yl)-2-chloropyridine 4-(4-bromo-1H-imidazol-1-yl)-2-chloropyridine 1353856-20-8 C8H5BrClN3
2-oxa-7-azaspiro[4.4]nonane hydrochloride 2-oxa-7-azaspiro[4.4]nonane hydrochloride 1419590-58-1 C7H14ClNO
3-Hydroxy-2-bromo-6-trifluoromethylpyridine 3-Hydroxy-2-bromo-6-trifluoromethylpyridine 1211526-50-9 C6H3BrF3NO
2-chloro-3-(trifluoromethyl)pyridine 1-oxide 2-chloro-3-(trifluoromethyl)pyridine 1-oxide 164464-57-7 C6H3ClF3NO
4-Chloro-2-iodopyridine 4-Chloro-2-iodopyridine 22918-03-2 C5H3ClIN
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
(2E,9E)-N'2,N'9-dicyano-1,3,8,10-tetraoxo-1,3,8,10-tetrahydroanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-2,9-bis(carboximidamide) (2E,9E)-N'2,N'9-dicyano-1,3,8,10-tetraoxo-1,3,8,10-tetrahydroanthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-2,9-bis(carboximidamide) 143992-61-4 C28H12N8O4
s,s-Dimethyl-β-propiolactone s,s-Dimethyl-β-propiolactone
6-Bromo-3-chloropicolinic acid 6-Bromo-3-chloropicolinic acid 1060815-76-0 C6H3BrClNO2
1-(4-(trifluoromethyl)phenyl)-1H-pyrazol-4-amine 1-(4-(trifluoromethyl)phenyl)-1H-pyrazol-4-amine 1251264-73-9 C10H8F3N3
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
5-bromo-4-(2-fluoropropan-2-yl)pyrimidine 5-bromo-4-(2-fluoropropan-2-yl)pyrimidine 1823944-93-9 C7H8BrFN2
3-bromo-1-methyl-1H-Pyrrolo[2,3-c]pyridine 3-bromo-1-methyl-1H-Pyrrolo[2,3-c]pyridine 956003-06-8 C8H7BrN2
4-(3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 4-(3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine 1366131-54-5 C17H26BNO3
exo-8-boc-8-azabicyclo[3.2.1]octan-2-amine exo-8-boc-8-azabicyclo[3.2.1]octan-2-amine 1408074-65-6 C12H22N2O2
Tert-butyl 4-(2-aminopyridin-4-yl)piperidine-1-carboxylate Tert-butyl 4-(2-aminopyridin-4-yl)piperidine-1-carboxylate 1415812-95-1 C15H23N3O2
1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazole 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazole 1607838-14-1 C16H21BN2O2
3-Bromo-4-(piperidin-1-yl)pyridine 3-Bromo-4-(piperidin-1-yl)pyridine 4556-56-3 C10H13BrN2
5-Bromo-7-chlorobenzofuran 5-Bromo-7-chlorobenzofuran 1194375-29-5 C8H4BrClO
4-chloro-6-(4-chlorophenyl)pyrimidin-2-amine 4-chloro-6-(4-chlorophenyl)pyrimidin-2-amine 875233-32-2 C10H7Cl2N3
(5-(aminomethyl)furan-2-yl)methanol (5-(aminomethyl)furan-2-yl)methanol 88910-22-9 C6H9NO2
ETHYL 8-CHLORO-6-(TRIFLUOROMETHYL)IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLATE ETHYL 8-CHLORO-6-(TRIFLUOROMETHYL)IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLATE 353258-31-8 C11H8ClF3N2O2
7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline 7-bromo-2-(1-methyl-1H-pyrazol-4-yl)Quinoxaline 1083325-87-4 C12H9BrN4
9-(biphenyl-3-yl)-carbazol-3-yl boronic acid 9-(biphenyl-3-yl)-carbazol-3-yl boronic acid 1416814-68-0 C24H18BNO2
B-(4-cyclopropyl-3-pyridinyl)boronic acid B-(4-cyclopropyl-3-pyridinyl)boronic acid 1428882-23-8 C8H10BNO2
6-(pyridin-4-yl)pyridin-2-amine 6-(pyridin-4-yl)pyridin-2-amine 39883-36-8 C10H9N3
1-methyl-4-aminoimidazole-2-carboxylic acid methyl ester hydrochloride 1-methyl-4-aminoimidazole-2-carboxylic acid methyl ester hydrochloride 480433-71-4 C6H10ClN3O2
2-chloro-4-(1H-pyrrol-1-yl)Pyrimidine 2-chloro-4-(1H-pyrrol-1-yl)Pyrimidine 1251534-07-2 C8H6ClN3
5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide 1272353-82-8 C25H20N6O2S
3-bromo-5-[(tetrahydro-3-furanyl)oxy]Pyridine 3-bromo-5-[(tetrahydro-3-furanyl)oxy]Pyridine 1289152-44-8 C9H10BrNO2
(S)-3-(4-Bromophenyl)piperidine (S)-3-(4-Bromophenyl)piperidine 1335523-82-4 C11H14BrN
4-(2-chloropyrimidin-5-yl)morpholine 4-(2-chloropyrimidin-5-yl)morpholine 952582-22-8 C8H10ClN3O
1-Pyrrolidinecarboxylic acid, 2-[(5-bromo-1H-indol-3-yl)carbonyl]-, phenylmethyl ester, (S)- 1-Pyrrolidinecarboxylic acid, 2-[(5-bromo-1H-indol-3-yl)carbonyl]-, phenylmethyl ester, (S)- 199659-03-5 C21H19BrN2O3
3-Bromo-6-(trifluoromethyl)pyridine-2-carbaldehyde 3-Bromo-6-(trifluoromethyl)pyridine-2-carbaldehyde 1227573-28-5 C7H3BrF3NO
5-(2-chloro-phenyl)-pyridin-2-ylamine 5-(2-chloro-phenyl)-pyridin-2-ylamine 875166-78-2 C11H9ClN2
2-(o-tolyl)-3-pyridinamine 2-(o-tolyl)-3-pyridinamine 886508-16-3 C12H12N2
2-p-tolylpyridin-4-ylamine 2-p-tolylpyridin-4-ylamine 1010075-63-4 C12H12N2
2-bromo-5-pyrrolidin-1-ylpyrazine 2-bromo-5-pyrrolidin-1-ylpyrazine 1001050-21-0 C8H10BrN3
3-bromo-5-(4-methylphenyl)-1H-1,2,4-triazole(SALTDATA: FREE) 3-bromo-5-(4-methylphenyl)-1H-1,2,4-triazole(SALTDATA: FREE) 1227465-72-6 C9H8BrN3
(R)-1-(1H-Benzimidazol-2-yl)-3-methylbutylamine Hydrochloride (R)-1-(1H-Benzimidazol-2-yl)-3-methylbutylamine Hydrochloride 1235643-62-5 C12H18ClN3
2,7-Diaza-spiro[4.5]decan-3-one 2,7-Diaza-spiro[4.5]decan-3-one 1158750-89-0 C8H14N2O
3-Hydroxy-2-Methylpyridine-d3 3-Hydroxy-2-Methylpyridine-d3 1185315-05-2 C6H4D3NO
4-Thioxo-2-iMidazolidinone 4-Thioxo-2-iMidazolidinone 16310-60-4 C3H4N2OS
5-DesaMino 5-Oxo-2,5-dihydro LaMotrigine 5-DesaMino 5-Oxo-2,5-dihydro LaMotrigine 252186-78-0 C9H6Cl2N4O
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-chloro-2-(2-fluorophenyl)pyridine 4-chloro-2-(2-fluorophenyl)pyridine 918530-84-4 C11H7ClFN
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
3-ethynyl-5-Methylpyridine 3-ethynyl-5-Methylpyridine 30413-53-7 C8H7N
(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-BenzothiazolaMine, 4-broMo-7-fluoro- 2-BenzothiazolaMine, 4-broMo-7-fluoro- 942473-89-4 C7H4BrFN2S
2,6-Dichloro-4-fluoropyridine 2,6-Dichloro-4-fluoropyridine 52074-49-4 C5H2Cl2FN
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
4-cyclobutylpyridin-3-aMine 4-cyclobutylpyridin-3-aMine 1374665-67-4 C9H12N2
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
4-(Ethoxycarbonyl)pyridine-2-boronic acid pinacol ester 4-(Ethoxycarbonyl)pyridine-2-boronic acid pinacol ester 1241898-91-8 C14H20BNO4
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
3-oxa-1,8-diazaspiro[4.5]decan-2-one 3-oxa-1,8-diazaspiro[4.5]decan-2-one 945947-99-9 C7H12N2O2
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
4-BroMo-1-(tetrahydrofuran-3-yl)-1H-pyrazole 4-BroMo-1-(tetrahydrofuran-3-yl)-1H-pyrazole 1040377-07-8 C7H9BrN2O
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
2-Chloro-4-(3-fluorophenyl)-1,3,5-triazine 2-Chloro-4-(3-fluorophenyl)-1,3,5-triazine 1053658-51-7 C9H5ClFN3
2-(3-Methylphenyl)-Morpholine HCl 2-(3-Methylphenyl)-Morpholine HCl 62008-56-4 C11H15NO
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
5-broMo-N-(diphenylMethylene)thiazol-2-aMine 5-broMo-N-(diphenylMethylene)thiazol-2-aMine 498574-68-8 C16H11BrN2S
a,a-diMethyl-2-FuranMethanaMine HCl a,a-diMethyl-2-FuranMethanaMine HCl 153002-42-7 C7H11NO
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