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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
2-Bromo-5-methylpyridine-d6 2-Bromo-5-methylpyridine-d6 1374665-50-5 C6H6BrN
2-Bromo-6-(morpholino)pyridine-d11 2-Bromo-6-(morpholino)pyridine-d11 1643575-33-0 C9H11BrN2O
2-Bromo-6-(n-propoxy)pyridine-d10 2-Bromo-6-(n-propoxy)pyridine-d10 1643576-49-1 C8H10BrNO
2-Bromo-6-ethoxypyridine-d8 2-Bromo-6-ethoxypyridine-d8 1643576-47-9 C7H8BrNO
2-Chloro-3-cyano-6-(iso-propyl-d7)-pyridine 2-Chloro-3-cyano-6-(iso-propyl-d7)-pyridine 1185319-75-8 C9H9ClN2
2-Chloro-3-trifluoromethyl-6-(n-propyl-d7)-pyridine 2-Chloro-3-trifluoromethyl-6-(n-propyl-d7)-pyridine 1185316-68-0 C9H9ClF3N
2-Chloro-6-(ethyl-d5)-4-aminopyridine 2-Chloro-6-(ethyl-d5)-4-aminopyridine 1185313-32-9 C7H9ClN2
2-Cyano-6-(n-propyl-d7)-pyridine-4-boronic acid 2-Cyano-6-(n-propyl-d7)-pyridine-4-boronic acid 2225174-14-9 C9H11BN2O2
2-Fluoro-6-(tert-butyl-d9)-pyridine-4-boronic acid 2-Fluoro-6-(tert-butyl-d9)-pyridine-4-boronic acid 2225154-83-4 C9H13BFNO2
3-Amino-6-(ethoxy-d5)-pyridazine 3-Amino-6-(ethoxy-d5)-pyridazine 1643576-79-7 C6H9N3O
3-Amino-6-(iso-propoxy-d7)-pyridazine 3-Amino-6-(iso-propoxy-d7)-pyridazine 1643564-23-1 C7H11N3O
3-Amino-6-(tert-butyl-d9)-pyridazine 3-Amino-6-(tert-butyl-d9)-pyridazine 1643542-59-9 C8H4D9N3
3-Bromo-(2-methyl-5-ethyl-d8)-pyridine 3-Bromo-(2-methyl-5-ethyl-d8)-pyridine 1643538-77-5 C8H10BrN
3-Bromo-(6-methyl-5-ethyl-d8)-pyridine 3-Bromo-(6-methyl-5-ethyl-d8)-pyridine 1643538-58-2 C8H10BrN
3-Bromo-[4-methyl-6-(iso-propyl)-d10]-pyridine 3-Bromo-[4-methyl-6-(iso-propyl)-d10]-pyridine 1643537-54-5 C9H12BrN
3-Bromo-[5-(sec-butyl)-4-methyl-d12]-pyridine 3-Bromo-[5-(sec-butyl)-4-methyl-d12]-pyridine 1643538-21-9 C10H14BrN
3-Bromo-5-(ethoxy-d5)-pyridine 3-Bromo-5-(ethoxy-d5)-pyridine 1643543-85-4 C7H8BrNO
3-Bromo-5-(iso-propoxy)pyridine-d10 3-Bromo-5-(iso-propoxy)pyridine-d10 1643576-17-3 C8H10BrNO
3-Bromo-5-(n-propoxy)pyridine-d10 3-Bromo-5-(n-propoxy)pyridine-d10 1643564-29-7 C8H10BrNO
3-Bromo-5-ethoxycarbonylpyridine-d8 3-Bromo-5-ethoxycarbonylpyridine-d8 1643579-70-7 C8H8BrNO2
3-Bromo-5-methoxycarbonylpyridine-d6 3-Bromo-5-methoxycarbonylpyridine-d6 1643564-34-4 C7H6BrNO2
3-Bromo-6-(ethoxy-d5)-pyridazine 3-Bromo-6-(ethoxy-d5)-pyridazine 1185315-06-3 C6H7BrN2O
3-Bromo-6-(iso-butyl-d9)-pyridazine 3-Bromo-6-(iso-butyl-d9)-pyridazine 1643538-98-0 C8H11BrN2
3-Bromo-6-(methyl-d3)-pyridazine 3-Bromo-6-(methyl-d3)-pyridazine 1185318-32-4 C5H2BrD3N2
3-Bromo-6-(morpholino)pyridine-d11 3-Bromo-6-(morpholino)pyridine-d11 1643564-25-3 C9BrD11N2O
3-Bromo-6-(pyrrolidino)pyridazine-d10 3-Bromo-6-(pyrrolidino)pyridazine-d10 1643576-27-5 C8H10BrN3
3-Bromo-6-(sec-butyl-d9)-pyridazine 3-Bromo-6-(sec-butyl-d9)-pyridazine 1643543-21-8 C8H11BrN2
3-Bromo-6-ethylpyridazine-d7 3-Bromo-6-ethylpyridazine-d7 1643539-38-1 C6H7BrN2
3-Bromopyridazine-d3 3-Bromopyridazine-d3 1643576-70-8 C4H3BrN2
3-Hydroxy-6-(iso-propyl-d7)-pyridine 3-Hydroxy-6-(iso-propyl-d7)-pyridine 1185317-67-2 C8H11NO
4-(sec-Butyl-d9)-pyridine-2-boronic acid pinacol ester 4-(sec-Butyl-d9)-pyridine-2-boronic acid pinacol ester 2223004-18-8 C15H17BD9NO3
4-[(tert-Butoxy)pyridine-d12]-2-boronic acid pinacol ester 4-[(tert-Butoxy)pyridine-d12]-2-boronic acid pinacol ester 2223029-29-4 C15H24BNO3
4-Amino-5-cyano-2-(methyl-d3)-pyrimidine 4-Amino-5-cyano-2-(methyl-d3)-pyrimidine 1185309-90-3 C6H3D3N4
4-Bromo-(3-methyl-6-ethyl-d8)-pyridine 4-Bromo-(3-methyl-6-ethyl-d8)-pyridine 1643562-87-1 C8H10BrN
4-Bromo-2-(dimethylamono-13C, d3)pyrimidine 4-Bromo-2-(dimethylamono-13C, d3)pyrimidine 1227959-04-7 C6HBrD6N2
4-Bromo-2-(ethyl-d5)-6-trifluoromethylpyridine 4-Bromo-2-(ethyl-d5)-6-trifluoromethylpyridine 1643538-12-8 C8H7BrF3N
4-Bromo-2-(iso-propyl-d7)-pyridine 4-Bromo-2-(iso-propyl-d7)-pyridine 1185311-32-3 C8H10BrN
4-Bromo-2-(piperidino)pyridine-d13 4-Bromo-2-(piperidino)pyridine-d13 1643537-78-3 C10H13BrN2
4-Bromo-2-(pyrrolidino-d8)-pyridine 4-Bromo-2-(pyrrolidino-d8)-pyridine 1643542-43-1 C9H3BrD8N2
4-Bromo-2-(tert-butyl-d9)-6-trifluoromethylpyridine 4-Bromo-2-(tert-butyl-d9)-6-trifluoromethylpyridine 1643543-01-4 C10H2BrD9F3N
4-Bromo-2-[(N-methylpiperazin-1-yl)pyridine-d14] 4-Bromo-2-[(N-methylpiperazin-1-yl)pyridine-d14] 1643579-77-4 C10H14BrN3
4-Bromo-2-cyano-6-(iso-propyl-d7)-pyridine 4-Bromo-2-cyano-6-(iso-propyl-d7)-pyridine 1643543-60-5 C9H9BrN2
4-Bromo-2-diethylaminopyridine-d13 4-Bromo-2-diethylaminopyridine-d13 1643579-76-3 C9H13BrN2
4-Bromo-2-methylpyridine-d6 4-Bromo-2-methylpyridine-d6 1643537-68-1 C6H6BrN
4-Bromo-2-trifluoromethyl-6-(n-propoxy-d7)-pyridine 4-Bromo-2-trifluoromethyl-6-(n-propoxy-d7)-pyridine 1643539-54-1 C9H2BrD7F3NO
4-Chloro-2-amino-6-(ethyl-d5)-pyrimidine 4-Chloro-2-amino-6-(ethyl-d5)-pyrimidine 1185306-57-3 C6H3ClD5N3
4-Chloro-5-methyl-2-(ethyl-d5)-pyrimidine 4-Chloro-5-methyl-2-(ethyl-d5)-pyrimidine 1185309-83-4 C7H9ClN2
4-Chloro-5-methyl-2-(n-propoxy-d7)-pyrimidine 4-Chloro-5-methyl-2-(n-propoxy-d7)-pyrimidine 1185308-61-5 C8H11ClN2O
4-Chloro-6-methyl-2-(ethoxy-d5)-pyrimidine 4-Chloro-6-methyl-2-(ethoxy-d5)-pyrimidine 1185309-30-1 C7H9ClN2O
4-Chloro-6-methyl-2-(methyl-d3)-pyrimidine 4-Chloro-6-methyl-2-(methyl-d3)-pyrimidine 1185309-13-0 C6H4ClD3N2
5-(iso-Butyl-d9)-pyridine-2-boronic acid pinacol ester 5-(iso-Butyl-d9)-pyridine-2-boronic acid pinacol ester 2223050-33-5 C15H17BD9NO3
5-[(tert-Butyl)pyridine-d12]-2-boronic acid pinacol ester 5-[(tert-Butyl)pyridine-d12]-2-boronic acid pinacol ester 2223052-68-2 C15H24BNO2
5-Bromo-[2-(iso-propoxy)-4-methyl-d10]-pyrimidine 5-Bromo-[2-(iso-propoxy)-4-methyl-d10]-pyrimidine 1643564-81-1 C8H11BrN2O
5-Bromo-2-(iso-propoxy-d7)-pyrimidine 5-Bromo-2-(iso-propoxy-d7)-pyrimidine 1643539-05-2 C7H2BrD7N2O
5-Bromo-2-(tert-butoxy-d9)-pyrimidine 5-Bromo-2-(tert-butoxy-d9)-pyrimidine 1643537-83-0 C8H11BrN2O
5-Bromo-2-chloro-4-(n-propyl-d7)-pyrimidine 5-Bromo-2-chloro-4-(n-propyl-d7)-pyrimidine 1643564-52-6 C7H8BrClN2
5-Bromo-4-chloro-2-(piperidino-d10)-pyrimidine 5-Bromo-4-chloro-2-(piperidino-d10)-pyrimidine 1643579-55-8 C9H11BrClN3
6-(Ethyl-d5)-pyridine-2-boronic acid pinacol ester 6-(Ethyl-d5)-pyridine-2-boronic acid pinacol ester 2223045-06-3 C13H17BD5NO3
6-[(n-Propyl)pyridine-d10]-2-boronic acid pinacol ester 6-[(n-Propyl)pyridine-d10]-2-boronic acid pinacol ester 2223054-90-6 C14H22BNO2
1,3-DIMETHYL-4-NITRO-1H-PYRAZOLE 1,3-DIMETHYL-4-NITRO-1H-PYRAZOLE 3920-38-5 C5H7N3O2
8-Bromoquinoxaline-5-carbonitrile 8-Bromoquinoxaline-5-carbonitrile 2101944-52-7 C9H4BrN3
3-(3-bromo-1H-1,2,4-triazol-5-yl)pyridine 3-(3-bromo-1H-1,2,4-triazol-5-yl)pyridine 1219571-83-1 C7H5BrN4
7-BROMO-1H-INDOLE-3-CARBALDEHYDE 7-BROMO-1H-INDOLE-3-CARBALDEHYDE 115666-21-2 C9H6BrNO
6-AZACYTOSINE 6-AZACYTOSINE 931-85-1 C3H4N4O
2-(4-methylphenyl)pyridin-3-ol 2-(4-methylphenyl)pyridin-3-ol 36739-30-7 C12H11NO
2-OXO-PYRROLIDINE-3-CARBOXYLIC ACID ETHYL ESTER 2-OXO-PYRROLIDINE-3-CARBOXYLIC ACID ETHYL ESTER 36821-26-8 C7H11NO3
3,5-DIMETHYL-4-NITROISOXAZOLE 3,5-DIMETHYL-4-NITROISOXAZOLE 1123-49-5 C5H6N2O3
Benzyl (2R,4S)-4-amino-2-methylpyrrolidine-1-carboxylate Benzyl (2R,4S)-4-amino-2-methylpyrrolidine-1-carboxylate 2165506-16-9 C13H18N2O2
6'-Bromo-8'-chloro-1',5'-dioxo-1',5'-dihydro-2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-4-carbonitrile 6'-Bromo-8'-chloro-1',5'-dioxo-1',5'-dihydro-2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-4-carbonitrile 1849593-46-9 C13H11BrClN3O2
5-[1-(hydroxyimino)ethyl]-4-methylpyrimidin-2-amine 5-[1-(hydroxyimino)ethyl]-4-methylpyrimidin-2-amine 1050886-14-0 C7H10N4O
2-BROMO-4-METHYL-1H-IMIDAZOLE 2-BROMO-4-METHYL-1H-IMIDAZOLE 23328-88-3 C4H5BrN2
1-(3,4,5-Trihydroxypentanoyl)-β-carboline 1-(3,4,5-Trihydroxypentanoyl)-β-carboline 180995-40-8 C16H16N2O4
(6-Methyl-1H-benzimidazol-2-yl)methanol (6-Methyl-1H-benzimidazol-2-yl)methanol 20034-02-0 C9H10N2O
4-(2-bromoethyl)pyridine hydrobromide 4-(2-bromoethyl)pyridine hydrobromide 120277-01-2 C7H9Br2N
1-{[(tert-butoxy)carbonyl]amino}-5-oxopyrrolidine-3-carboxylic acid 1-{[(tert-butoxy)carbonyl]amino}-5-oxopyrrolidine-3-carboxylic acid 1354952-07-0 C10H16N2O5
3-deuterio-thiophene 3-deuterio-thiophene 1192-05-8 C4H3DS
(2-(2-(trifluoromethyl)phenyl)pyrimidin-5-yl)boronic acid (2-(2-(trifluoromethyl)phenyl)pyrimidin-5-yl)boronic acid 2225172-07-4 C11H8BF3N2O2
(2-(4-(methyl-d3)piperazin-1-yl-2,2,3,3,5,5,6,6-d8)pyrimidin-5-yl)boronic acid (2-(4-(methyl-d3)piperazin-1-yl-2,2,3,3,5,5,6,6-d8)pyrimidin-5-yl)boronic acid 2241877-07-4 C9H4BD11N4O2
(2-(4-methoxyphenyl)pyrimidin-5-yl)boronic acid (2-(4-methoxyphenyl)pyrimidin-5-yl)boronic acid 2225175-11-9 C11H11BN2O3
(2-(methoxy-d3)-6-(methyl-d3)pyridin-4-yl)boronic acid (2-(methoxy-d3)-6-(methyl-d3)pyridin-4-yl)boronic acid 2241875-97-6 C7H10BNO3
(2-(methyl-d3)pyrimidin-5-yl)boronic acid (2-(methyl-d3)pyrimidin-5-yl)boronic acid 2241865-77-8 C5H7BN2O2
(2-(p-tolyl)pyrimidin-5-yl)boronic acid (2-(p-tolyl)pyrimidin-5-yl)boronic acid 2225175-08-4 C11H11BN2O2
(2-(pyrimidin-5-yl)pyridin-4-yl)boronic acid (2-(pyrimidin-5-yl)pyridin-4-yl)boronic acid 2225155-89-3 C9H8BN3O2
(2-(thiophen-2-yl)pyrimidin-5-yl)boronic acid (2-(thiophen-2-yl)pyrimidin-5-yl)boronic acid 2225172-17-6 C8H7BN2O2S
(2,5-bis(methyl-d3)pyridin-4-yl)boronic acid (2,5-bis(methyl-d3)pyridin-4-yl)boronic acid 2241875-99-8 C7H10BNO2
(2-cyano-6-(methyl-d3)pyridin-4-yl)boronic acid (2-cyano-6-(methyl-d3)pyridin-4-yl)boronic acid 2241875-93-2 C7H7BN2O2
(2-hydroxy-6-(piperidin-2-yl)pyridin-4-yl)boronic acid (2-hydroxy-6-(piperidin-2-yl)pyridin-4-yl)boronic acid 2256708-73-1 C10H15BN2O3
(5-(furan-2-yl)pyridin-3-yl)boronic acid (5-(furan-2-yl)pyridin-3-yl)boronic acid 2225176-19-0 C9H8BNO3
(6-(2-(methyl-d3)propan-2-yl-1,1,1,3,3,3-d6)pyridin-3-yl)boronic acid (6-(2-(methyl-d3)propan-2-yl-1,1,1,3,3,3-d6)pyridin-3-yl)boronic acid 2241875-62-5 C9H14BNO2
(6-(methyl-d3)-5-(propan-2-yl-d7)pyridin-3-yl-2,4-d2)boronic acid (6-(methyl-d3)-5-(propan-2-yl-d7)pyridin-3-yl-2,4-d2)boronic acid 2241870-48-2 C9H14BNO2
[2-(METHOXYCARBONYL)-6-BROMOPYRIDIN-4-YL]BORONIC ACID [2-(METHOXYCARBONYL)-6-BROMOPYRIDIN-4-YL]BORONIC ACID 2225174-53-6 C7H7BBrNO4
1-(methyl-d3)-4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-2,2,3,3,5,5,6,6-d8 1-(methyl-d3)-4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-2,2,3,3,5,5,6,6-d8 2241870-11-9 C16H15BD11N3O2
2-(1,4-dioxan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-(1,4-dioxan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2222996-07-6 C13H20BNO4S
2-(1H-Pyrazol-1-yl)pyridine-4-boronic acid 2-(1H-Pyrazol-1-yl)pyridine-4-boronic acid 1644060-50-3 C8H8BN3O2
2-(1H-Pyridin-2-one)pyrimidine-5-boronic acid pinacol ester 2-(1H-Pyridin-2-one)pyrimidine-5-boronic acid pinacol ester 2223049-88-3 C15H18BN3O3
2-(2-Chlorophenyl)pyridine-3-boronic acid pinacol ester 2-(2-Chlorophenyl)pyridine-3-boronic acid pinacol ester 2223045-87-0 C17H19BClNO2
2-(2-Imidazol-1-yl)pyridine-5-boronic acid 2-(2-Imidazol-1-yl)pyridine-5-boronic acid 1341209-38-8 C8H8BN3O2
2-(2-Methyl-4-fluorophenyl)pyridine-3-boronic acid 2-(2-Methyl-4-fluorophenyl)pyridine-3-boronic acid 2225174-40-1 C12H11BFNO2
2-(2-TETRAHYDROFURANYL)PYRIDINE-4-BORONIC ACID 2-(2-TETRAHYDROFURANYL)PYRIDINE-4-BORONIC ACID 2225153-21-7 C9H12BNO3
2-(2-Tolyl)pyridine-3-boronic acid pinacol ester 2-(2-Tolyl)pyridine-3-boronic acid pinacol ester 2223037-98-5 C18H22BNO2
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