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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
(S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile (S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile 1448440-39-8 C7H9F2N3O
1-N-Boc-5-bromo-3,6-dihydro-2H-pyridine 1-N-Boc-5-bromo-3,6-dihydro-2H-pyridine 1415841-82-5 C10H16BrNO2
5,6,7,8-Tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid ethyl ester 5,6,7,8-Tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid ethyl ester 951627-01-3 C9H13N3O2
Isopropyl 1H-imidazole-1-carboxylate Isopropyl 1H-imidazole-1-carboxylate 82998-18-3 C7H10N2O2
Pyridinium o-iodoxybenzoate Pyridinium o-iodoxybenzoate 1380548-11-7 C12H10INO4
Di-Fluoro ethylene carbonate Di-Fluoro ethylene carbonate 311810-76-1 C3H2F2O3
AKOS B019512 AKOS B019512 5775-82-6 C5H7BrN2
3-AMINO-PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-AMINO-PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 862372-66-5 C10H18N2O4
(S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE (S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE 118949-61-4 C17H23N3O2
6-CHLORO-4-NITRO-1H-INDAZOLE 6-CHLORO-4-NITRO-1H-INDAZOLE 885519-50-6 C7H4ClN3O2
3-tert-Butoxycarbonylphenylboronic acid 3-tert-Butoxycarbonylphenylboronic acid 220210-56-0 C11H15BO4
Phosphonium, [(3'R)-1'-[(1,1-dimethylethoxy)carbonyl]-2-oxo[1,3'-bipyrrolidin]-3-yl]triphenyl-, bromide Phosphonium, [(3'R)-1'-[(1,1-dimethylethoxy)carbonyl]-2-oxo[1,3'-bipyrrolidin]-3-yl]triphenyl-, bromide 376653-42-8 C31H36BrN2O3P
4,4'-Difluorodiphenylketone-3,3'-disulfonic acid 4,4'-Difluorodiphenylketone-3,3'-disulfonic acid 625392-06-5 C13H8F2O7S2
7'-brmomspiro[fluorene-9,5'-indeno[1,2-b]pyridine] 7'-brmomspiro[fluorene-9,5'-indeno[1,2-b]pyridine] 1666128-76-2 C24H14BrN
4-bromo-6-morpholinopyridin-3-amine hydrochloride 4-bromo-6-morpholinopyridin-3-amine hydrochloride 1381934-18-4 C9H12BrN3O
5-bromo-4-chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine 5-bromo-4-chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine 1477532-48-1 C7H3BrClN3O2
8-Ethyl-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-8H-pyrido[2,3-d]pyrimidin-7-one 8-Ethyl-2-[[4-(4-methylpiperazin-1-yl)phenyl]amino]-8H-pyrido[2,3-d]pyrimidin-7-one 211245-14-6 C20H24N6O
3-(5-bromo-2-furanyl)-pyridine 3-(5-bromo-2-furanyl)-pyridine 55484-31-6 C9H6BrNO
4-(4-FLUOROPHENYL)-1,3-THIAZOLE 4-(4-FLUOROPHENYL)-1,3-THIAZOLE 383145-29-7 C9H6FNS
4-chloro-6-(tetrahydro-2H-pyran-4-yl)pyrimidine 4-chloro-6-(tetrahydro-2H-pyran-4-yl)pyrimidine 1350356-47-6 C9H11ClN2O
2-(1-pyrrolidinyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)Pyridine 2-(1-pyrrolidinyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)Pyridine 1401350-36-4 C15H23BN2O2
1-chloro-4-methoxypyrido[3,4-d]pyridazine 1-chloro-4-methoxypyrido[3,4-d]pyridazine 56400-55-6 C8H6ClN3O
5-(2-methyl-4-thiazolyl)-2-Pyridinamine 5-(2-methyl-4-thiazolyl)-2-Pyridinamine 1159820-16-2 C9H9N3S
5-bromo-2-propylPyridine 5-bromo-2-propylPyridine 1225434-01-4 C8H10BrN
4-chloro-2-(1H-pyrrol-1-yl)Pyrimidine 4-chloro-2-(1H-pyrrol-1-yl)Pyrimidine 1251534-08-3 C8H6ClN3
(3S,5R)-5-methylpyrrolidin-3-ol hydrochloride (3S,5R)-5-methylpyrrolidin-3-ol hydrochloride 1107658-78-5 C5H12ClNO
2-Cyclopropoxy-4-fluoropyridine 2-Cyclopropoxy-4-fluoropyridine 1394978-07-4 C8H8FNO
(R)-4-(2-chloro-6-(methylthiomethyl)pyrimidin-4-yl)-3-methylmorpholine (R)-4-(2-chloro-6-(methylthiomethyl)pyrimidin-4-yl)-3-methylmorpholine 1352227-15-6 C11H16ClN3OS
2-(5-(4-amino-2-fluoro-5-nitro-3-(tetrahydrofuran-2-yl)phenyl)pyrimidin-2-yl)propan-2-ol 2-(5-(4-amino-2-fluoro-5-nitro-3-(tetrahydrofuran-2-yl)phenyl)pyrimidin-2-yl)propan-2-ol 1384984-28-4 C17H19FN4O4
4-(3-Fluorophenyl)Pyridin-2-Amine 4-(3-Fluorophenyl)Pyridin-2-Amine 1159815-31-2 C11H9FN2
5-chloro-4-iodopyridin-2-amine 5-chloro-4-iodopyridin-2-amine 1260667-65-9 C5H4ClIN2
5-bromo-2-hydrazinylpyridine hydrochloride 5-bromo-2-hydrazinylpyridine hydrochloride 1295647-30-1 C5H7BrClN3
4-HYDROXY-2-PHENYLPYRIDINE 4-HYDROXY-2-PHENYLPYRIDINE 3262-40-6 C11H9NO
3-isopropylpyridin-2-amine 3-isopropylpyridin-2-amine 1101060-79-0 C8H12N2
3,3-DIMETHYLPYRROLIDINE-2-CARBOXYLIC ACID hydrochloride 3,3-DIMETHYLPYRROLIDINE-2-CARBOXYLIC ACID hydrochloride 61406-78-8 C7H14ClNO2
1-(Pyridin-4-yl)-1H-imidazol-2-amine 1-(Pyridin-4-yl)-1H-imidazol-2-amine 1256803-78-7 C8H8N4
3-(Pyrrolidin-1-yl)pyridin-4-amine 3-(Pyrrolidin-1-yl)pyridin-4-amine 144864-27-7 C9H13N3
3-Morpholinopyridin-4-amine 3-Morpholinopyridin-4-amine 144864-28-8 C9H13N3O
6-Morpholinopyridin-2-amine 6-Morpholinopyridin-2-amine 400774-96-1 C9H13N3O
6-Bromoindole-3-carboxylic acid 6-Bromoindole-3-carboxylic acid 101774-27-0 C9H6BrNO2
4-(1-piperidyl)pyrimidin-2-amine 4-(1-piperidyl)pyrimidin-2-amine 69193-22-2 C9H14N4
4H-1,2,4-Triazole, 3-bromo-4-ethyl- 4H-1,2,4-Triazole, 3-bromo-4-ethyl- 64907-56-8 C4H6BrN3
4-Bromo-1,3,5-trimethyl-1H-pyrazole 4-Bromo-1,3,5-trimethyl-1H-pyrazole 15801-69-1 C6H9BrN2
1-Benzyl-4-bromo-1H-1,2,3-triazole 1-Benzyl-4-bromo-1H-1,2,3-triazole 31875-99-7 C9H8BrN3
2-Boc-3,4-dihydro-1H-pyrrolo-[1,2-a]pyrazine-6-carboxylic acid 2-Boc-3,4-dihydro-1H-pyrrolo-[1,2-a]pyrazine-6-carboxylic acid 1363380-86-2 C13H18N2O4
4-Bromo-3-(pyrrolidin-1-yl)pyridine 4-Bromo-3-(pyrrolidin-1-yl)pyridine 1563531-11-2 C9H11BrN2
4-(4-Bromo-2-(trifluoromethyl)phenyl)morpholine 4-(4-Bromo-2-(trifluoromethyl)phenyl)morpholine 1373522-70-3 C11H11BrF3NO
2-Fluoro-4-methoxy-5-(trifluoromethyl)pyridine 2-Fluoro-4-methoxy-5-(trifluoromethyl)pyridine 1227511-84-3 C7H5F4NO
(S)-3-(PYRROLIDIN-2-YL)PYRIDINE DIHYDROCHLORIDE (S)-3-(PYRROLIDIN-2-YL)PYRIDINE DIHYDROCHLORIDE 287966-92-1 C9H14Cl2N2
3-(difluoromethyl)pyrrolidine hydrochloride 3-(difluoromethyl)pyrrolidine hydrochloride 1376176-56-5 C5H10ClF2N
Chloro[1,3-bis(cyclohexyl)2H-imidazol-2-ylidene]gold(I), 98% Chloro[1,3-bis(cyclohexyl)2H-imidazol-2-ylidene]gold(I), 98% 852445-87-5 C15H24AuClN2
4,4'-((3',4',5',6'-tetrakis(4-(pyridin-4-ylethynyl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-diyl)bis(ethyne-2,1-diyl))dipyridine 4,4'-((3',4',5',6'-tetrakis(4-(pyridin-4-ylethynyl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-diyl)bis(ethyne-2,1-diyl))dipyridine 591215-25-7 C84H48N6
methyl 4-bromo-6-methoxypyridine-3-carboxylate methyl 4-bromo-6-methoxypyridine-3-carboxylate 1256819-58-5 C8H8BrNO3
ffBTZ-C8-2Br ffBTZ-C8-2Br 1393528-97-6 C14H17Br2F2N3
5',3'']Terpyridine 5',3'']Terpyridine 106047-31-8 C15H11N3
2,3,4-trimethyl-5,6-diphenylpyridine 2,3,4-trimethyl-5,6-diphenylpyridine 1004547-55-0 C20H19N
MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER 212650-43-6 C10H17NO5
(R)-4-BENZYL-1,3-OXAZOLIDINE-2-THIONE (R)-4-BENZYL-1,3-OXAZOLIDINE-2-THIONE 190970-58-2 C10H11NOS
2-Methyl-4-phenyl-1H-imidazole 2-Methyl-4-phenyl-1H-imidazole 13739-48-5 C10H10N2
1H-1,2,4-Triazole-3,5-diamine 1H-1,2,4-Triazole-3,5-diamine 1455-77-2 C2H5N5
1-(4-Nitrophenyl)-1H-pyrazole 1-(4-Nitrophenyl)-1H-pyrazole 3463-30-7 C9H7N3O2
5-(CHLOROMETHYL)-1,3-DIMETHYL-1H-PYRAZOLE 5-(CHLOROMETHYL)-1,3-DIMETHYL-1H-PYRAZOLE 852227-86-2 C6H9ClN2
(1,3-DIMETHYL-1H-PYRAZOL-5-YL)METHANOL (1,3-DIMETHYL-1H-PYRAZOL-5-YL)METHANOL 57012-20-1 C6H10N2O
(R)-(+)-1-[(1-METHYL-2-PYRROLIDINYL)METHYL]PIPERIDINE (R)-(+)-1-[(1-METHYL-2-PYRROLIDINYL)METHYL]PIPERIDINE 155726-05-9 C11H22N2
6-BROMO-1,4-BENZODIOXANE 6-BROMO-1,4-BENZODIOXANE 52287-51-1 C8H7BrO2
IID432 IID432 3094992-69-2 C19H19N7O
(3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol (3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol 5605-46-9 C12H17NO4S
2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3S,4S)- 2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3S,4S)- 905854-03-7 C23H19N3O2
4-Chloro-2-iodo-5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine 4-Chloro-2-iodo-5-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine 1420885-94-4 C14H17ClF3IN2OSi
(2-(tert-butyl)pyridin-4-yl)boronic acid (2-(tert-butyl)pyridin-4-yl)boronic acid 2000187-68-6 C9H14BNO2
(2-cyclohexylpyridin-4-yl)boronic acid (2-cyclohexylpyridin-4-yl)boronic acid 2225177-02-4 C11H16BNO2
(6-cyclopentylpyridin-3-yl)boronic acid (6-cyclopentylpyridin-3-yl)boronic acid 2225171-69-5 C10H14BNO2
2-(3-chlorophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(3-chlorophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223053-54-9 C17H19BClNO2
2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4'-bipyridine 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4'-bipyridine 2223036-53-9 C16H19BN2O2
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(o-tolyl)pyridine 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(o-tolyl)pyridine 1402166-74-8 C18H22BNO2
2-(4-fluorophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(4-fluorophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 1402172-87-5 C17H19BFNO2
2-(tetrahydrofuran-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(tetrahydrofuran-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223005-61-4 C15H22BNO3
2-isobutyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-isobutyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223038-06-8 C15H24BNO2
4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)benzonitrile 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)benzonitrile 2223037-79-2 C18H19BN2O2
4-(2-methoxyphenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(2-methoxyphenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 1402226-79-2 C18H22BNO3
4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)benzonitrile 4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)benzonitrile 2223039-53-8 C18H19BN2O2
4-(furan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(furan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223038-69-3 C15H18BNO3
5-(4-methyl-1H-imidazol-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(4-methyl-1H-imidazol-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223029-11-4 C15H20BN3O2
5-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)pyrimidine 5-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)pyrimidine 2223011-41-2 C15H18BN3O2
5-(piperidin-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(piperidin-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 1402166-05-5 C16H25BN2O2
5-isobutyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-isobutyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223035-76-3 C15H24BNO2
tert-butyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)pyrrolidine-1-carboxylate tert-butyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)pyrrolidine-1-carboxylate 2222996-54-3 C20H31BN2O4
tert-butyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)piperidine-1-carboxylate tert-butyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)piperidine-1-carboxylate 2222996-12-3 C21H33BN2O4
tert-butyl 3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)pyrrolidine-1-carboxylate tert-butyl 3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)pyrrolidine-1-carboxylate 2222996-69-0 C20H31BN2O4
3,6-DI-4-PYRIDYL-1,2,4,5-TETRAZINE 3,6-DI-4-PYRIDYL-1,2,4,5-TETRAZINE 57654-36-1 C12H8N6
ETHYL 5-ACETYLISOXASOLE-3-CARBOXYLATE ETHYL 5-ACETYLISOXASOLE-3-CARBOXYLATE 104776-70-7 C8H9NO4
Cytidine 5'-diphosphate trisodium salt Cytidine 5'-diphosphate trisodium salt 34393-59-4 C9H16N3NaO11P2
Parylene Parylene 25722-33-2 (C8H8)n
5-thien-2-yl-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-2-carbohydrazide 5-thien-2-yl-7-(trifluoromethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-2-carbohydrazide 832739-24-9 C12H12F3N5OS
5-bromo-2-(cyclohex-1-en-1-yl)pyridine 5-bromo-2-(cyclohex-1-en-1-yl)pyridine 1159821-19-8 C11H12BrN
4,6-dibromo-2-methylpyrimidine 4,6-dibromo-2-methylpyrimidine 1598222-27-5 C5H4Br2N2
3-p-Tolyl-1H-[1,2,4]triazole 3-p-Tolyl-1H-[1,2,4]triazole 23195-60-0 C9H9N3
3-fluoro-4-(pyrrolidin-1-ylmethyl)benzaldehyde 3-fluoro-4-(pyrrolidin-1-ylmethyl)benzaldehyde 1443353-89-6 C12H14FNO
C-(1-BENZYL-PYRROLIDIN-3-YL)-METHYLAMINE C-(1-BENZYL-PYRROLIDIN-3-YL)-METHYLAMINE 93138-61-5 C12H18N2
3'-bromo-3,4'-bipyridine 3'-bromo-3,4'-bipyridine 1356406-39-7 C10H7BrN2
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