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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
1-Chloro-9H-carbazole 1-Chloro-9H-carbazole 5599-70-2 C12H8ClN
4-Bromo-5-methylpyridin-2(1H)-one 4-Bromo-5-methylpyridin-2(1H)-one 1227578-85-9 C6H6BrNO
4-BROMO-1-PHENYL-1H-PYRAZOLE 4-BROMO-1-PHENYL-1H-PYRAZOLE 15115-52-3 C9H7BrN2
4-(3-Tolyl)furan-2-boronic acid 4-(3-Tolyl)furan-2-boronic acid 2096337-56-1 C11H11BO3
5-(2-Trifluoromethylphenyl)furan-2-boronic acid 5-(2-Trifluoromethylphenyl)furan-2-boronic acid 2096331-53-0 C11H8BF3O3
2-(4-Bromo-1-pyrazolyl)ethyl Acetate 2-(4-Bromo-1-pyrazolyl)ethyl Acetate 1215073-99-6 C7H9BrN2O2
2-ethyl-2,3-dihydro-2-(1H-imidazol-5-yl)-1H-Inden-1-one 2-ethyl-2,3-dihydro-2-(1H-imidazol-5-yl)-1H-Inden-1-one 104054-82-2 C14H14N2O
4-(2-Bromo-pyrimidin-4-yl)- piperidine-1-carboxylic acid tert-butyl ester 4-(2-Bromo-pyrimidin-4-yl)- piperidine-1-carboxylic acid tert-butyl ester 1398603-45-6 C14H20BrN3O2
6-Bromo-5-methoxy-3H-imidazo[4,5-b]pyridine 6-Bromo-5-methoxy-3H-imidazo[4,5-b]pyridine 2708194-57-2 C7H6BrN3O
N3,N3-Dimethylpyridine-2,3-diamine N3,N3-Dimethylpyridine-2,3-diamine 50426-30-7 C7H11N3
Phosphinic acid, di-4-morpholinyl-, butyl ester (9CI) Phosphinic acid, di-4-morpholinyl-, butyl ester (9CI) 5326-05-6 C12H25N2O4P
4(1H)-Pyrimidinone, 2-(4-methoxyphenyl)- 4(1H)-Pyrimidinone, 2-(4-methoxyphenyl)- 88627-13-8 C11H10N2O2
4-ETHYL-1,3-THIAZOL-5-AMINE 4-ETHYL-1,3-THIAZOL-5-AMINE 1249955-33-6 C5H8N2S
5-bromo-2-(4-methoxyphenyl)pyrimidine 5-bromo-2-(4-methoxyphenyl)pyrimidine 177727-12-7 C11H9BrN2O
N-ACETOACETYLMORPHOLINE N-ACETOACETYLMORPHOLINE 16695-54-8 C8H13NO3
2-chloro-4-phenylbenzo[h]quinazoline 2-chloro-4-phenylbenzo[h]quinazoline 4786-80-5 C18H11ClN2
4-Bromo-2-fluoro-5-(trifluoromethyl)pyridine 4-Bromo-2-fluoro-5-(trifluoromethyl)pyridine 1227600-03-4 C6H2BrF4N
Alkyne NHS ester (hexynoic acid NHS ester) Alkyne NHS ester (hexynoic acid NHS ester) 906564-59-8 C10H11NO4
5,5'-difluoro-2,2'-bipyridine 5,5'-difluoro-2,2'-bipyridine 1041837-79-9 C10H6F2N2
Benzo[b]naphtho[2,3-d]furan, 3-bromo- Benzo[b]naphtho[2,3-d]furan, 3-bromo- 1256544-32-7 C16H9BrO
1-Ethyl-3-methylimidazolium Tricyanomethanide 1-Ethyl-3-methylimidazolium Tricyanomethanide 666823-18-3 C10H11N5
6-BENZOTHIAZOLECARBONITRILE 6-BENZOTHIAZOLECARBONITRILE 58249-61-9 C8H4N2S
4,4',4'',4'''-(2,2',4,4',6,6'-hexamethyl-[1,1'-biphenyl]-3,3',5,5'-tetrayl)tetrapyridine 4,4',4'',4'''-(2,2',4,4',6,6'-hexamethyl-[1,1'-biphenyl]-3,3',5,5'-tetrayl)tetrapyridine 809274-33-7 C38H34N4
1-(4-bromo-6-methoxypyridin-2-yl)ethanone 1-(4-bromo-6-methoxypyridin-2-yl)ethanone 1060815-49-7 C8H8BrNO2
5-(bromomethyl)-1-methyl-4-nitro-1H-imidazole 5-(bromomethyl)-1-methyl-4-nitro-1H-imidazole 1017279-02-5 C5H6BrN3O2
(2-propylpyridin-4-yl)boronic acid (2-propylpyridin-4-yl)boronic acid 2225180-61-8 C8H12BNO2
1-phenyl-N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)methanimine 1-phenyl-N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)methanimine 2223056-49-1 C18H21BN2O2
2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)benzonitrile 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)benzonitrile 2223028-81-5 C18H19BN2O2
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(m-tolyl)pyridine 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(m-tolyl)pyridine 1402172-10-4 C18H22BNO2
2-(furan-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(furan-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223027-64-1 C15H18BNO3
2-(tetrahydro-2H-pyran-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(tetrahydro-2H-pyran-3-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223007-04-1 C16H24BNO3
3-(1,4-dioxan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(1,4-dioxan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2222997-05-7 C15H22BNO4
3-(tetrahydrofuran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(tetrahydrofuran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223009-72-9 C15H22BNO3
4-(3-chlorophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(3-chlorophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223012-96-0 C17H19BClNO2
4-(4-chlorophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(4-chlorophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223029-98-7 C17H19BClNO2
4-(sec-butyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(sec-butyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2222997-01-3 C15H24BNO2
4-(Tetrahydropyran-3-yl)pyridine-2-boronic acid pinacol ester 4-(Tetrahydropyran-3-yl)pyridine-2-boronic acid pinacol ester 1402166-22-6 C16H26BNO4
5-(1H-imidazol-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(1H-imidazol-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223029-26-1 C14H18BN3O2
5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)thiazole 5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)thiazole 2223043-56-7 C14H17BN2O2S
5-(furan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(furan-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223033-15-4 C15H18BNO3
5-(tetrahydrofuran-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(tetrahydrofuran-2-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223009-19-4 C15H22BNO3
6'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-[1,2'-bipyridin]-2-one 6'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-[1,2'-bipyridin]-2-one 1352754-45-0 C16H19BN2O3
tert-butyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)morpholine-4-carboxylate tert-butyl 2-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)morpholine-4-carboxylate 2222996-17-8 C20H31BN2O5
tert-butyl 2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)morpholine-4-carboxylate tert-butyl 2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)morpholine-4-carboxylate 2222996-16-7 C20H31BN2O5
tert-butyl 3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)piperidine-1-carboxylate tert-butyl 3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)piperidine-1-carboxylate 2222996-30-5 C21H33BN2O4
6-CHLOROIMIDAZO[2,1-B]THIAZOLE 6-CHLOROIMIDAZO[2,1-B]THIAZOLE 23576-81-0 C5H3ClN2S
2-AMINO-4-BROMOTHIAZOLE 2-AMINO-4-BROMOTHIAZOLE 502145-18-8 C3H3BrN2S
4-Chloroquinazoline 4-Chloroquinazoline 5190-68-1 C8H5ClN2
5-bromo-2-cyclohexyloxy-1,3-thiazole 5-bromo-2-cyclohexyloxy-1,3-thiazole 1086382-70-8 C9H12BrNOS
7-CHLOROPYRIDO[3,2-D]PYRIMIDIN-4(3H)-ONE 7-CHLOROPYRIDO[3,2-D]PYRIMIDIN-4(3H)-ONE 897360-16-6 C7H4ClN3O
4-chloro-2-cyclopropyl-6-propylpyrimidine 4-chloro-2-cyclopropyl-6-propylpyrimidine 1153409-24-5 C10H13ClN2
(S)-(+)-2-(AMINOMETHYL)PYRROLIDINE (S)-(+)-2-(AMINOMETHYL)PYRROLIDINE 69500-64-7 C5H12N2
5-(PYRIDIN-3-YL)PYRAZIN-2-AMINE 5-(PYRIDIN-3-YL)PYRAZIN-2-AMINE 1159816-78-0 C9H8N4
6-(2-methoxyphenyl)pyridazin-3-ol 6-(2-methoxyphenyl)pyridazin-3-ol 79129-26-3 C11H10N2O2
5,6-dibromopyridine-2-carbonitrile 5,6-dibromopyridine-2-carbonitrile 1260678-87-2 C6H2Br2N2
5-Amino-3,4,5,6-tetrahydro-2H-[1,3]bipyridinyl-3-ol 5-Amino-3,4,5,6-tetrahydro-2H-[1,3]bipyridinyl-3-ol 1563530-83-5 C10H15N3O
3-BROMO-5-MORPHOLINOPYRIDIN-2-AMINE 3-BROMO-5-MORPHOLINOPYRIDIN-2-AMINE 1254301-05-7 C9H12BrN3O
4-Chloro-[3,3]bipyridinyl-2-ylamine 4-Chloro-[3,3]bipyridinyl-2-ylamine 1381935-06-3 C10H8ClN3
4-bromo-2-cyclopentyloxy-1,3-thiazole 4-bromo-2-cyclopentyloxy-1,3-thiazole 1289092-17-6 C8H10BrNOS
4-(4-FLUOROPHENYL)PYRIDIN-2(1H)-ONE 4-(4-FLUOROPHENYL)PYRIDIN-2(1H)-ONE 1159817-47-6 C11H8FNO
3-bromo-2-tert-butylpyridine 3-bromo-2-tert-butylpyridine 1417518-07-0 C9H12BrN
2-Phenyl-2,3-dihydro-1H-perimidine 2-Phenyl-2,3-dihydro-1H-perimidine 19564-07-9 C17H14N2
2-cyclopropyl-6-propylpyrimidin-4-ol 2-cyclopropyl-6-propylpyrimidin-4-ol 1153408-73-1 C10H14N2O
2-cyclopropyl-6-isopropylpyrimidin-4-ol 2-cyclopropyl-6-isopropylpyrimidin-4-ol 1019017-11-8 C10H14N2O
2-Cyclopentylthiazol-5-amine 2-Cyclopentylthiazol-5-amine 1159819-10-9 C8H12N2S
2,5-dioxopyrrolidin-1-yl 5-{2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl}pentanoate 2,5-dioxopyrrolidin-1-yl 5-{2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl}pentanoate 85718-04-3 C14H19N3O5S
2-(tert-butoxycarbonyl)-2,6-diazaspiro[3.4]octane-8-carboxylic acid 2-(tert-butoxycarbonyl)-2,6-diazaspiro[3.4]octane-8-carboxylic acid 1823981-11-8 C12H20N2O4
2-(4,5-dimethyl-2-thienyl)pyrrolidine 2-(4,5-dimethyl-2-thienyl)pyrrolidine 1018163-24-0 C10H15NS
2-(4-TRIFLUOROMETHOXY-PHENYL)-PYRROLIDINE, HYDROCHLORIDE 2-(4-TRIFLUOROMETHOXY-PHENYL)-PYRROLIDINE, HYDROCHLORIDE 1185121-45-2 C11H13ClF3NO
2-(4-CHLOROBENZYLTHIO)-1H-BENZO[D]IMIDAZOLE 2-(4-CHLOROBENZYLTHIO)-1H-BENZO[D]IMIDAZOLE 23976-76-3 C14H11ClN2S
(2R)-2,8-dimethyl-5-(trideuteriomethyl)-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol (2R)-2,8-dimethyl-5-(trideuteriomethyl)-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol 936230-75-0 C28H45D3O2
1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE 1-(TERT-BUTOXYCARBONYL)-2-PYRROLIDINONE 85909-08-6 C9H15NO3
(2-Ethyl-3-methyl-d8)-pyridine-4-boronic acid (2-Ethyl-3-methyl-d8)-pyridine-4-boronic acid 2225155-98-4 C8H12BNO2
(2-Methyl-6-morpholino-d11)-pyridine-4-boronic acid (2-Methyl-6-morpholino-d11)-pyridine-4-boronic acid 2225154-56-1 C10H15BN2O3
[2-(iso-Propyl)-5-methyl-d10]-pyridine-4-boronic acid [2-(iso-Propyl)-5-methyl-d10]-pyridine-4-boronic acid 2225177-36-4 C9H14BNO2
[2-Methyl-5-(iso-butyl)-d12]-pyridine-3-boronic acid [2-Methyl-5-(iso-butyl)-d12]-pyridine-3-boronic acid 2225174-07-0 C10H16BNO2
[2-Methyl-6-(iso-butyl)-d12]-pyridine-4-boronic acid [2-Methyl-6-(iso-butyl)-d12]-pyridine-4-boronic acid 2225173-98-6 C10H16BNO2
[3-Methyl-6-(tert-butyl)-d12]-pyridine-4-boronic acid [3-Methyl-6-(tert-butyl)-d12]-pyridine-4-boronic acid 2225173-73-7 C10H16BNO2
[4-Methyl-5-(iso-propyl)-d10]-pyridine-3-boronic acid [4-Methyl-5-(iso-propyl)-d10]-pyridine-3-boronic acid 2225181-34-8 C9H14BNO2
[4-Methyl-6-(iso-propyl)-d10]-pyridine-3-boronic acid [4-Methyl-6-(iso-propyl)-d10]-pyridine-3-boronic acid 2225170-76-1 C9H14BNO2
[6-Methyl-5-(n-propyl)-d10]-pyridine-3-boronic acid [6-Methyl-5-(n-propyl)-d10]-pyridine-3-boronic acid 2225154-63-0 C9H14BNO2
1-N-Boc-3,6-Dihydro-2H-4-bromopyridine(3,5,5-d3) 1-N-Boc-3,6-Dihydro-2H-4-bromopyridine(3,5,5-d3) 1357580-47-2 C10H16BrNO2
2-(Ethoxy-d5)-6-trifluoromethylpyridine-4-boronic acid 2-(Ethoxy-d5)-6-trifluoromethylpyridine-4-boronic acid 2225179-75-7 C8H9BF3NO3
2-(n-Propyl-d7)-pyridine-4-boronic acid 2-(n-Propyl-d7)-pyridine-4-boronic acid 2225172-75-6 C8H12BNO2
2,4-Dichloro-6-(ethyl-d7)-pyridine 2,4-Dichloro-6-(ethyl-d7)-pyridine 1185310-71-7 C7H7Cl2N
2,4-Dichloro-6-(methoxy-d3)-pyridine 2,4-Dichloro-6-(methoxy-d3)-pyridine 1185313-52-3 C6H2Cl2D3NO
2-[(n-Propoxy)pyridine-d10]-4-boronic acid 2-[(n-Propoxy)pyridine-d10]-4-boronic acid 2225174-62-7 C8H12BNO3
2-Amino-4-(Methyl-13C, d3)pyrimidine 2-Amino-4-(Methyl-13C, d3)pyrimidine 1227958-90-8 C5H4D3N3
2-Amino-4-(morpholinopyridine-d11) 2-Amino-4-(morpholinopyridine-d11) 1643579-79-6 C9H13N3O
2-Amino-4-[(n-propyl)pyridine-d10] 2-Amino-4-[(n-propyl)pyridine-d10] 1643576-90-2 C8H12N2
2-Amino-5-(methylpyridine-d6) 2-Amino-5-(methylpyridine-d6) 916979-10-7 C6H8N2
2-Amino-5-(tert-butyl)pyridine-d12 2-Amino-5-(tert-butyl)pyridine-d12 1643577-30-3 C9H14N2
2-Bromo-4-(iso-propoxy-d7)-pyridine 2-Bromo-4-(iso-propoxy-d7)-pyridine 1185311-41-4 C8H10BrNO
2-Bromo-4-(methoxy-d3-carbonyl)-pyridine 2-Bromo-4-(methoxy-d3-carbonyl)-pyridine 1643538-88-8 C7H4BrD3NO2
2-Bromo-4-morpholinopyridine-d11 2-Bromo-4-morpholinopyridine-d11 1643564-07-1 C9H11BrN2O
2-Bromo-5-(ethyl-d5)-pyrimidine 2-Bromo-5-(ethyl-d5)-pyrimidine 1643538-97-9 C6H2BrD5N2
2-Bromo-5-(sec-butyl-d9)-pyrimidine 2-Bromo-5-(sec-butyl-d9)-pyrimidine 1643563-16-9 C8H11BrN2
2-Bromo-5-ethylpyridine-d8 2-Bromo-5-ethylpyridine-d8 1643576-72-0 C7H8BrN
2-Bromo-5-methoxypyridine-d6 2-Bromo-5-methoxypyridine-d6 1643564-91-3 C6H6BrNO
2-Bromo-6-(iso-propoxy)pyridine-d10 2-Bromo-6-(iso-propoxy)pyridine-d10 1643575-90-9 C8BrD10NO
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