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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
4-(OXETAN-3-YL)PYRIDIN-2-AMINE 4-(OXETAN-3-YL)PYRIDIN-2-AMINE 1427501-89-0 C8H10N2O
4-(TERT-BUTYL)-1H-IMIDAZOL-2-AMINE HCL 4-(TERT-BUTYL)-1H-IMIDAZOL-2-AMINE HCL 1384100-95-1 C7H14ClN3
4-(2-Fluoro-phenyl)-thiazol-5-ylamine 4-(2-Fluoro-phenyl)-thiazol-5-ylamine 1248481-02-8 C9H7FN2S
3-Bromo-2-propoxy-pyridin-4-ylamine 3-Bromo-2-propoxy-pyridin-4-ylamine 1563530-65-3 C8H11BrN2O
3-BROMO-4-ETHYLPYRIDIN-2-AMINE 3-BROMO-4-ETHYLPYRIDIN-2-AMINE 1381938-68-6 C7H9BrN2
3-(3-Fluoro-phenyl)-1H-[1,2,4]triazole 3-(3-Fluoro-phenyl)-1H-[1,2,4]triazole 1279202-08-2 C8H6FN3
2-Ethylthiazol-4-amine 2-Ethylthiazol-4-amine 1159819-40-5 C5H8N2S
2-(thiophen-3-yl)pyridin-4-amine 2-(thiophen-3-yl)pyridin-4-amine 1159818-65-1 C9H8N2S
4-CHLORO-6-METHYLQUINAZOLINE 4-CHLORO-6-METHYLQUINAZOLINE 58421-79-7 C9H7ClN2
2-AMINO-4-BROMO-1-METHYLIMIDAZOLE 2-AMINO-4-BROMO-1-METHYLIMIDAZOLE 151597-82-9 C4H6BrN3
1-(pyrimidin-2-yl)azetidin-3-ol 1-(pyrimidin-2-yl)azetidin-3-ol 1341070-48-1 C7H9N3O
1-(2,2,2-trifluoroethyl)pyrazole-3-carbaldehyde 1-(2,2,2-trifluoroethyl)pyrazole-3-carbaldehyde 1310379-34-0 C6H5F3N2O
TERT-BUTYL4-(2-AMINOPYRIDIN-3-YL)PIPERIDINE-1-CARBOXYLATE TERT-BUTYL4-(2-AMINOPYRIDIN-3-YL)PIPERIDINE-1-CARBOXYLATE 1245914-95-7 C15H23N3O2
(2-Methyl-6-methoxycarbonyl-d6)-pyridine-4-boronic acid (2-Methyl-6-methoxycarbonyl-d6)-pyridine-4-boronic acid 2225170-55-6 C8H10BNO4
(4-Methyl-5-ethyl-d8)-pyridine-3-boronic acid (4-Methyl-5-ethyl-d8)-pyridine-3-boronic acid 2225179-73-5 C8H12BNO2
[3-Methyl-6-(iso-butyl)-d12]-pyridine-4-boronic acid [3-Methyl-6-(iso-butyl)-d12]-pyridine-4-boronic acid 2225180-34-5 C10H16BNO2
2-(Diethylamino-d10)-pyridine-4-boronic acid 2-(Diethylamino-d10)-pyridine-4-boronic acid 2225180-08-3 C9H15BN2O2
2-(Diethylaminopyridine-d13)-4-boronic acid 2-(Diethylaminopyridine-d13)-4-boronic acid 2225181-68-8 C9H15BN2O2
2-(iso-Butyl-d9)-6-trifluoromethylpyridine-4-boronic acid 2-(iso-Butyl-d9)-6-trifluoromethylpyridine-4-boronic acid 2225154-54-9 C10H13BF3NO2
2-(iso-Butyl-d9)-pyrimidine-5-boronic acid 2-(iso-Butyl-d9)-pyrimidine-5-boronic acid 2225170-57-8 C8H4BD9N2O2
2-(Methylethylamino-d8)-pyrimidine-5-boronic acid 2-(Methylethylamino-d8)-pyrimidine-5-boronic acid 2225172-68-7 C7H4BD8N3O2
2-(n-Propoxy-d7)-pyrimidine-5-boronic acid 2-(n-Propoxy-d7)-pyrimidine-5-boronic acid 2225176-43-0 C7H11BN2O3
2-(sec-Butyl-d9)-pyrimidine-5-boronic acid 2-(sec-Butyl-d9)-pyrimidine-5-boronic acid 2225153-04-6 C8H4BD9N2O2
2,4-Dichloro-6-(iso-propyl-d7)-pyridine 2,4-Dichloro-6-(iso-propyl-d7)-pyridine 1185313-46-5 C8H2Cl2D7N
2-Amino-4-[(N-methylpiperazin-1-yl)pyridine-d14] 2-Amino-4-[(N-methylpiperazin-1-yl)pyridine-d14] 1643575-82-9 C10H16N4
2-Amino-5-(iso-propyl-d7)-pyridine 2-Amino-5-(iso-propyl-d7)-pyridine 1185317-74-1 C8H12N2
2-Amino-5-(sec-butyl-d9)-pyridine 2-Amino-5-(sec-butyl-d9)-pyridine 1643562-85-9 C9H14N2
2-Amino-5-[(N-methylpiperazin-d11)-1-yl]pyridine 2-Amino-5-[(N-methylpiperazin-d11)-1-yl]pyridine 1643537-52-3 C10H16N4
2-Amino-6-(methyl-d3)-pyridine 2-Amino-6-(methyl-d3)-pyridine 1185317-21-8 C6H5D3N2
2-Amino-6-(piperidin-4-yl)pyridine-d8 2-Amino-6-(piperidin-4-yl)pyridine-d8 1622844-10-3 C10H7D8N3
2-Bromo-4-(iso-butyl-d9)-pyridine 2-Bromo-4-(iso-butyl-d9)-pyridine 1643563-62-5 C9H12BrN
2-Bromo-4-(n-propoxy)pyridine-d10 2-Bromo-4-(n-propoxy)pyridine-d10 1643564-12-8 C8BrD10NO
2-Bromo-4-(piperidino-d10)-pyridine 2-Bromo-4-(piperidino-d10)-pyridine 1643563-34-1 C10H3BrD10N2
2-Bromo-4-ethylpyridine-d8 2-Bromo-4-ethylpyridine-d8 1643576-09-3 C7H8BrN
2-Bromo-5-(iso-propyl)pyridine-d10 2-Bromo-5-(iso-propyl)pyridine-d10 1643577-27-8 C8H10BrN
2-Bromo-5-(iso-propyl-d7)-pyrimidine 2-Bromo-5-(iso-propyl-d7)-pyrimidine 1643563-02-3 C7H9BrN2
2-Bromo-5-(morpholino-d8)-pyridine 2-Bromo-5-(morpholino-d8)-pyridine 1643543-29-6 C9H11BrN2O
2-Bromo-5-[N-Boc-(piperazin-d8)-1-yl]pyridine 2-Bromo-5-[N-Boc-(piperazin-d8)-1-yl]pyridine 1643576-74-2 C14H14BrD8N3O2
2-Bromo-5-ethoxypyridine-d8 2-Bromo-5-ethoxypyridine-d8 1643564-76-4 C7BrD8NO
2-Bromo-6-(methoxycarbonyl)pyridine-d6 2-Bromo-6-(methoxycarbonyl)pyridine-d6 1643575-69-2 C7BrD6NO2
2-Bromo-6-(morpholino-d8)-pyridine 2-Bromo-6-(morpholino-d8)-pyridine 1643538-76-4 C9H11BrN2O
2-Chloro-3-cyano-6-(methyl-d3)-pyridine 2-Chloro-3-cyano-6-(methyl-d3)-pyridine 1185316-91-9 C7H2ClD3N2
2-Chloro-4-(Methyl-d3)-pyrimidine-5-boronic acid 2-Chloro-4-(Methyl-d3)-pyrimidine-5-boronic acid 2225174-67-2 C5H6BClN2O2
2-Chloro-6-(tert-butyl-d9)-pyridine-4-boronic acid 2-Chloro-6-(tert-butyl-d9)-pyridine-4-boronic acid 2225179-32-6 C9H4BClD9NO2
2-Fluoro-6-(iso-butyl-d9)-pyridine-4-boronic acid 2-Fluoro-6-(iso-butyl-d9)-pyridine-4-boronic acid 2225179-70-2 C9H13BFNO2
2-Hydroxy-6-(iso-propyl-d7)-pyridine 2-Hydroxy-6-(iso-propyl-d7)-pyridine 1185310-93-3 C8H11NO
2-Pivalamido(pyridine-d3)-4-boronic acid 2-Pivalamido(pyridine-d3)-4-boronic acid 2225173-04-4 C10H15BN2O3
3-Amino-5-(iso-propyl-d7)-pyridine 3-Amino-5-(iso-propyl-d7)-pyridine 1643537-62-5 C8H12N2
3-Amino-5-(tert-butyl-d9)-pyridine 3-Amino-5-(tert-butyl-d9)-pyridine 1643539-20-1 C9H5D9N2
3-Amino-6-(methylethylamino-d8)-pyridazine 3-Amino-6-(methylethylamino-d8)-pyridazine 1643576-75-3 C7H4D8N4
3-Amino-6-(pyrrolidino-d8)-pyridazine 3-Amino-6-(pyrrolidino-d8)-pyridazine 1643543-20-7 C8H12N4
3-Bromo-(5,6-dimethyl-d6)-pyridine 3-Bromo-(5,6-dimethyl-d6)-pyridine 1643537-64-7 C7H8BrN
3-Bromo-[4-methyl-5-(iso-propyl)-d10]-pyridine 3-Bromo-[4-methyl-5-(iso-propyl)-d10]-pyridine 1643577-28-9 C9H12BrN
3-Bromo-[5-methyl-6-(tert-butyl)-d12]-pyridine 3-Bromo-[5-methyl-6-(tert-butyl)-d12]-pyridine 1643538-37-7 C10H14BrN
3-Bromo-[6-methyl-5-(sec-butyl)-d12]-pyridine 3-Bromo-[6-methyl-5-(sec-butyl)-d12]-pyridine 1643562-82-6 C10H14BrN
3-Bromo-5-(methoxy-d3-carbonyl)pyridine 3-Bromo-5-(methoxy-d3-carbonyl)pyridine 1643576-68-4 C7H6BrNO2
3-Bromo-5-(morpholino)pyridine-d11 3-Bromo-5-(morpholino)pyridine-d11 1643542-04-4 C9BrD11N2O
3-Bromo-5-(n-propyl)pyridine-d10 3-Bromo-5-(n-propyl)pyridine-d10 1643541-95-0 C8BrD10N
3-Bromo-5-(tert-butyl-d9)-pyridine 3-Bromo-5-(tert-butyl-d9)-pyridine 1643542-44-2 C9H3BrD9N
3-Bromo-5-ethoxypyridine-d8 3-Bromo-5-ethoxypyridine-d8 1643541-99-4 C7H8BrNO
3-Bromo-6-(dimethylamino-d6)-pyridazine 3-Bromo-6-(dimethylamino-d6)-pyridazine 1643542-18-0 C6H8BrN3
3-Bromo-6-(ethoxy-d5)-pyridine 3-Bromo-6-(ethoxy-d5)-pyridine 1417656-26-8 C7H8BrNO
3-Bromo-6-(methoxy-d3)-pyridazine 3-Bromo-6-(methoxy-d3)-pyridazine 1185306-50-6 C5H5BrN2O
3-Bromo-6-(piperidino)pyridazine-d12 3-Bromo-6-(piperidino)pyridazine-d12 1643575-55-6 C9H12BrN3
3-Bromo-6-(pyrrolidino)pyridine-d11 3-Bromo-6-(pyrrolidino)pyridine-d11 1643576-94-6 C9H11BrN2
3-Bromo-6-cyanopyridazine-d2 3-Bromo-6-cyanopyridazine-d2 1643576-76-4 C5H2BrN3
3-Bromo-6-fluoropyridazine-d2 3-Bromo-6-fluoropyridazine-d2 1643576-01-5 C4H2BrFN2
3-Chloro-4-methyl-6-(n-propyl-d7)-pyridazine 3-Chloro-4-methyl-6-(n-propyl-d7)-pyridazine 1185317-69-4 C8H11ClN2
3-Chloro-6-(methoxy-d3)pyridine 3-Chloro-6-(methoxy-d3)pyridine 1185310-18-2 C6H6ClNO
4-(iso-Butyl-d9)-pyridine-2-boronic acid pinacol ester 4-(iso-Butyl-d9)-pyridine-2-boronic acid pinacol ester 2223029-73-8 C15H17BD9NO3
4-Amino-2-(n-propyl-d7)-pyridine 4-Amino-2-(n-propyl-d7)-pyridine 1185317-87-6 C8H5D7N2
4-Bromo-(2-methyl-6-piperidino-d13)-pyridine 4-Bromo-(2-methyl-6-piperidino-d13)-pyridine 1643538-26-4 C11H15BrN2
4-Bromo-[2-(methyl)-6-(methoxycarbonyl)-d6]-pyridine 4-Bromo-[2-(methyl)-6-(methoxycarbonyl)-d6]-pyridine 1643577-65-4 C8H8BrNO2
4-Bromo-[2-methyl-6-(tert-butyl)-d12]-pyridine 4-Bromo-[2-methyl-6-(tert-butyl)-d12]-pyridine 1643542-62-4 C10H14BrN
4-Bromo-[3-methyl-6-(sec-butyl)-d12]-pyridine 4-Bromo-[3-methyl-6-(sec-butyl)-d12]-pyridine 1643577-19-8 C10H14BrN
4-Bromo-2-(1-Hydroxy-1-methylethyl)pyridine-d9 4-Bromo-2-(1-Hydroxy-1-methylethyl)pyridine-d9 1643563-69-2 C8HBrD9NO
4-Bromo-2-(iso-propoxy)pyridine-d10 4-Bromo-2-(iso-propoxy)pyridine-d10 1643537-71-6 C8H10BrNO
4-Bromo-2-(methyl-d3)-6-trifluoromethylpyridine 4-Bromo-2-(methyl-d3)-6-trifluoromethylpyridine 1643538-44-6 C7H5BrF3N
4-Bromo-2-(n-propyl-d7)-pyrimidine 4-Bromo-2-(n-propyl-d7)-pyrimidine 1185317-03-6 C7H9BrN2
4-Bromo-2-(sec-butyl-d9)-6-cyanopyridine 4-Bromo-2-(sec-butyl-d9)-6-cyanopyridine 1643538-49-1 C10H11BrN2
4-Bromo-2-chloro-6-(n-propyl-d7)-pyridine 4-Bromo-2-chloro-6-(n-propyl-d7)-pyridine 1643577-67-6 C8H9BrClN
4-Bromo-2-fluoro-6-(iso-butyl-d9)-pyridine 4-Bromo-2-fluoro-6-(iso-butyl-d9)-pyridine 1643563-66-9 C9H11BrFN
4-Bromo-2-methoxypyridine-d6 4-Bromo-2-methoxypyridine-d6 1643576-45-7 C6BrD6NO
4-Chloro-2-methylthio-6-(methyl-d3)-pyrimidine 4-Chloro-2-methylthio-6-(methyl-d3)-pyrimidine 1185311-82-3 C6H7ClN2S
4-Chloro-5-fluoro-2-(iso-propyl-d7)-pyrimidine 4-Chloro-5-fluoro-2-(iso-propyl-d7)-pyrimidine 1185306-65-3 C7H8ClFN2
4-Chloro-5-methyl-2-(iso-propoxy-d7)-pyrimidine 4-Chloro-5-methyl-2-(iso-propoxy-d7)-pyrimidine 1185317-95-6 C8H11ClN2O
4-Chloro-6-amino-2-(ethyl-d5)-pyrimidine 4-Chloro-6-amino-2-(ethyl-d5)-pyrimidine 1185315-18-7 C6H8ClN3
4-Chloro-6-methyl-2-(ethyl-d5)-pyrimidine 4-Chloro-6-methyl-2-(ethyl-d5)-pyrimidine 1185314-85-5 C7H9ClN2
5-(Ethylpyridine-d8)-2-boronic acid pinacol ester 5-(Ethylpyridine-d8)-2-boronic acid pinacol ester 2223032-25-3 C13H20BNO2
5-(n-Propyl-d7)-pyridine-2-boronic acid pinacol ester 5-(n-Propyl-d7)-pyridine-2-boronic acid pinacol ester 2223052-21-7 C14H22BNO2
5-(tert-Butoxy-d9)-pyridine-3-boronic acid pinacol ester 5-(tert-Butoxy-d9)-pyridine-3-boronic acid pinacol ester 2223037-53-2 C15H24BNO3
5-[(n-Propyl)pyridine-d10]-2-boronic acid pinacol ester 5-[(n-Propyl)pyridine-d10]-2-boronic acid pinacol ester 2223040-37-5 C14H22BNO2
5-Bromo-2-(methylethylamino-d8)-pyrimidine 5-Bromo-2-(methylethylamino-d8)-pyrimidine 1643539-22-3 C7H10BrN3
5-Bromo-2-chloro-4-(ethyl-d5)-pyrimidine 5-Bromo-2-chloro-4-(ethyl-d5)-pyrimidine 1643542-06-6 C6H6BrClN2
5-Bromo-4-chloro-2-(diethylamino-d10)-pyrimidine 5-Bromo-4-chloro-2-(diethylamino-d10)-pyrimidine 1643542-93-1 C8H11BrClN3
5-Bromo-4-chloro-2-(methyl-d3)-pyrimidine 5-Bromo-4-chloro-2-(methyl-d3)-pyrimidine 1643562-80-4 C5HBrClD3N2
7-BROMO-1H-PYRROLO[3,2-C]PYRIDINE 7-BROMO-1H-PYRROLO[3,2-C]PYRIDINE 902837-42-7 C7H5BrN2
4-(4-bromo-3-methylphenyl)morpholine 4-(4-bromo-3-methylphenyl)morpholine 1366131-48-7 C11H14BrNO
6-BROMO-3-IODO (1H)INDAZOLE 6-BROMO-3-IODO (1H)INDAZOLE 885521-88-0 C7H4BrIN2
Substituted pyrazine Substituted pyrazine 2095311-51-4 C22H23N5O2
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