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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-Amino-5-(tert-butyl-d9)-pyridine 2-Amino-5-(tert-butyl-d9)-pyridine 1643538-23-1 C9H14N2
2-Amino-6-(n-propyl-d7)-pyridine 2-Amino-6-(n-propyl-d7)-pyridine 1185308-86-4 C8H5D7N2
2-Bromo-4-(diethylamino-d10)-pyridine 2-Bromo-4-(diethylamino-d10)-pyridine 1643563-28-3 C9H13BrN2
2-Bromo-4-(N-methylpiperizin-1-yl)pyridine-d14 2-Bromo-4-(N-methylpiperizin-1-yl)pyridine-d14 1643563-77-2 C10H14BrN3
2-Bromo-4-(n-propyl-d7)-pyridine 2-Bromo-4-(n-propyl-d7)-pyridine 1185308-58-0 C8H10BrN
2-Bromo-4-ethoxypyridine-d8 2-Bromo-4-ethoxypyridine-d8 1643563-54-5 C7H8BrNO
2-Bromo-4-methoxypyridine-d6 2-Bromo-4-methoxypyridine-d6 1643579-75-2 C6BrD6NO
2-Bromo-5-(iso-propyl-d7)-pyridine 2-Bromo-5-(iso-propyl-d7)-pyridine 1185313-25-0 C8H3BrD7N
2-Bromo-5-(n-propoxy-d7)-pyridine 2-Bromo-5-(n-propoxy-d7)-pyridine 1643576-28-6 C8H10BrNO
2-Bromo-5-(pyrrolidino)pyridine-d11 2-Bromo-5-(pyrrolidino)pyridine-d11 1643542-23-7 C9BrD11N2
2-Bromo-5-[(N-methylpiperazin-d11)-1-yl]pyridine 2-Bromo-5-[(N-methylpiperazin-d11)-1-yl]pyridine 1643538-79-7 C10H14BrN3
2-Bromo-6-(cyano-13C, 15N)pyridine 2-Bromo-6-(cyano-13C, 15N)pyridine 1227958-97-5 C6H3BrN2
2-Bromo-6-(dimethylamino-d6)-pyridine 2-Bromo-6-(dimethylamino-d6)-pyridine 1185310-67-1 C7H9BrN2
2-Bromo-6-(piperidino)pyridine-d13 2-Bromo-6-(piperidino)pyridine-d13 1643564-96-8 C10H13BrN2
2-Chloro-4-(methyl-d3)-5-cyclopropylpyrimidine 2-Chloro-4-(methyl-d3)-5-cyclopropylpyrimidine 1643538-02-6 C8H9ClN2
2-Chloro-6-(n-propyl-d7)-pyridine-4-boronic acid 2-Chloro-6-(n-propyl-d7)-pyridine-4-boronic acid 2225180-35-6 C8H11BClNO2
2-Fluoro-6-(ethyl-d5)-pyridine-4-boronic acid 2-Fluoro-6-(ethyl-d5)-pyridine-4-boronic acid 2225171-71-9 C7H9BFNO2
2-Hydroxy-6-(ethyl-d5)-pyridine 2-Hydroxy-6-(ethyl-d5)-pyridine 1185313-86-3 C7H9NO
2-Methylaminopyridine-d7 2-Methylaminopyridine-d7 1185319-89-4 C6H8N2
3-Amino-5-(iso-butyl-d9)-pyridine 3-Amino-5-(iso-butyl-d9)-pyridine 1643538-67-3 C9H14N2
3-Amino-5-(sec-butyl-d9)-pyridine 3-Amino-5-(sec-butyl-d9)-pyridine 1643538-64-0 C9H5D9N2
3-Amino-6-(methyl-d3)-pyridine 3-Amino-6-(methyl-d3)-pyridine 1185313-85-2 C6H5D3N2
3-Amino-6-(n-propyl-d7)-pyridine 3-Amino-6-(n-propyl-d7)-pyridine 1185317-48-9 C8H12N2
3-Bromo-(4-methyl-6-ethyl-d8)-pyridine 3-Bromo-(4-methyl-6-ethyl-d8)-pyridine 1643562-74-6 C8H10BrN
3-Bromo-[2-methyl-5-(sec-butyl)-d12]-pyridine 3-Bromo-[2-methyl-5-(sec-butyl)-d12]-pyridine 1643577-39-2 C10H14BrN
3-Bromo-[4-methyl-5-(iso-butyl)-d12]-pyridine 3-Bromo-[4-methyl-5-(iso-butyl)-d12]-pyridine 1643564-17-3 C10H14BrN
3-Bromo-[5-methyl-6-(sec-butyl)-d12]-pyridine 3-Bromo-[5-methyl-6-(sec-butyl)-d12]-pyridine 1643537-58-9 C10H14BrN
3-Bromo-[6-methyl-5-(n-propyl)-d10]-pyridine 3-Bromo-[6-methyl-5-(n-propyl)-d10]-pyridine 1643542-94-2 C9H12BrN
3-Bromo-2-fluoro-5-(methyl-d3)-pyridine 3-Bromo-2-fluoro-5-(methyl-d3)-pyridine 1185319-98-5 C6H5BrFN
3-Bromo-5-(methoxy-d3)-pyridine 3-Bromo-5-(methoxy-d3)-pyridine 1185317-09-2 C6H6BrNO
3-Bromo-5-(methylethylamino-d8)-pyridine 3-Bromo-5-(methylethylamino-d8)-pyridine 1643563-10-3 C8H11BrN2
3-Bromo-6-(dimethylamino)pyridazine-d8 3-Bromo-6-(dimethylamino)pyridazine-d8 1643543-63-8 C6BrD8N3
3-Bromo-6-(iso-propoxy-d7)-pyridine 3-Bromo-6-(iso-propoxy-d7)-pyridine 1643537-56-7 C8H10BrNO
3-Bromo-6-(methoxy)pyridine-d6 3-Bromo-6-(methoxy)pyridine-d6 1643564-79-7 C6H6BrNO
3-Bromo-6-(n-propoxy-d7)-pyridazine 3-Bromo-6-(n-propoxy-d7)-pyridazine 1643576-73-1 C7H2BrD7N2O
3-Bromo-6-(n-propyl-d7)-pyridine 3-Bromo-6-(n-propyl-d7)-pyridine 1185314-59-3 C8H10BrN
3-Bromo-6-(tert-butyl)pyridine-d12 3-Bromo-6-(tert-butyl)pyridine-d12 1643538-55-9 C9H12BrN
3-Bromo-6-ethylpyridine-d8 3-Bromo-6-ethylpyridine-d8 1643563-55-6 C7H8BrN
3-Chloro-4-methyl-6-(methyl-d3)-pyridazine 3-Chloro-4-methyl-6-(methyl-d3)-pyridazine 1185306-59-5 C6H7ClN2
4-(Ethoxy-d5)-pyridine-2-boronic acid pinacol ester 4-(Ethoxy-d5)-pyridine-2-boronic acid pinacol ester 2223036-48-2 C13H17BD5NO4
4-(Ethylpyridine-d8)-2-boronic acid pinacol ester 4-(Ethylpyridine-d8)-2-boronic acid pinacol ester 2223039-46-9 C13H20BNO2
4,6-Dichloro-2-(n-propoxy-d7)-pyrimidine 4,6-Dichloro-2-(n-propoxy-d7)-pyrimidine 1185316-64-6 C7H8Cl2N2O
4-Amino-2-(iso-propyl-d7)-pyridine 4-Amino-2-(iso-propyl-d7)-pyridine 1185315-88-1 C8H12N2
4-Bromo-(2-methyl-6-morpholino-d11)-pyridine 4-Bromo-(2-methyl-6-morpholino-d11)-pyridine 1643537-72-7 C10H13BrN2O
4-Bromo-[2-(iso-propyl)-3-methyl-d10]-pyridine 4-Bromo-[2-(iso-propyl)-3-methyl-d10]-pyridine 1643563-50-1 C9H12BrN
4-Bromo-[2-methyl-6-(n-propyl)-d10]-pyridine 4-Bromo-[2-methyl-6-(n-propyl)-d10]-pyridine 1643539-51-8 C9H12BrN
4-Bromo-[3-methyl-6-(n-propyl)-d10]-pyridine 4-Bromo-[3-methyl-6-(n-propyl)-d10]-pyridine 1643544-16-4 C9H12BrN
4-Bromo-2-(diethylamino-d10)-pyridine 4-Bromo-2-(diethylamino-d10)-pyridine 1643541-65-4 C9H13BrN2
4-Bromo-2-(iso-butyl)pyridine-d12 4-Bromo-2-(iso-butyl)pyridine-d12 1643564-88-8 C9H12BrN
4-Bromo-2-(methoxy-d3)-pyrimidine 4-Bromo-2-(methoxy-d3)-pyrimidine 1185311-54-9 C5H5BrN2O
4-Bromo-2-(methylamino-d3)-pyridine 4-Bromo-2-(methylamino-d3)-pyridine 1185308-19-3 C6H7BrN2
4-Bromo-2-(n-propoxy-d7)-pyrimidine 4-Bromo-2-(n-propoxy-d7)-pyrimidine 1185316-20-4 C7H9BrN2O
4-Bromo-2-(n-propyl-d7)-pyridine 4-Bromo-2-(n-propyl-d7)-pyridine 1185319-68-9 C8H3BrD7N
4-Bromo-2-(sec-butyl-d9)-6-chloropyridine 4-Bromo-2-(sec-butyl-d9)-6-chloropyridine 1643542-83-9 C9H11BrClN
4-Bromo-2-(sec-butyl-d9)-pyridine 4-Bromo-2-(sec-butyl-d9)-pyridine 1643539-44-9 C9H12BrN
4-Bromo-2-chloro-6-(methyl-d3)-pyridine 4-Bromo-2-chloro-6-(methyl-d3)-pyridine 1643538-53-7 C6H5BrClN
4-Bromo-2-fluoro-6-(ethyl-d5)-pyridine 4-Bromo-2-fluoro-6-(ethyl-d5)-pyridine 1643576-14-0 C7H7BrFN
4-Bromo-2-fluoro-6-(tert-butyl-d9)-pyridine 4-Bromo-2-fluoro-6-(tert-butyl-d9)-pyridine 1643539-37-0 C9H11BrFN
4-Chloro-2-methylthio-6-(iso-propyl-d7)-pyrimidine 4-Chloro-2-methylthio-6-(iso-propyl-d7)-pyrimidine 1185316-74-8 C8H11ClN2S
4-Chloro-5-trifluoromethyl-2-(n-propyl-d7)-pyrimidine 4-Chloro-5-trifluoromethyl-2-(n-propyl-d7)-pyrimidine 1185317-23-0 C8HClD7F3N2
4-Chloro-6-(phenyl-d5)-pyrimidine 4-Chloro-6-(phenyl-d5)-pyrimidine 1185318-27-7 C10H7ClN2
5-(tert-Butoxy-d9)-pyridine-2-boronic acid pinacol ester 5-(tert-Butoxy-d9)-pyridine-2-boronic acid pinacol ester 2223043-12-5 C15H24BNO3
5-Bromo-(2-ethoxy-4-methyl-d8)-pyrimidine 5-Bromo-(2-ethoxy-4-methyl-d8)-pyrimidine 1643542-09-9 C7H9BrN2O
5-Bromo-2-(diethylamino-d10)-pyrimidine 5-Bromo-2-(diethylamino-d10)-pyrimidine 1643544-14-2 C8H12BrN3
5-Bromo-2-(ethyl-d5)-pyrimidine 5-Bromo-2-(ethyl-d5)-pyrimidine 1185309-63-0 C6H2BrD5N2
5-Bromo-2-(methyl-d3-amino)-pyrimidine 5-Bromo-2-(methyl-d3-amino)-pyrimidine 1185316-10-2 C5H3BrD3N3
5-Bromo-2-(n-propoxy-d7)-pyrimidine 5-Bromo-2-(n-propoxy-d7)-pyrimidine 1643539-07-4 C7H9BrN2O
5-Bromo-2,4-(dimethyl-d6)-pyrimidine 5-Bromo-2,4-(dimethyl-d6)-pyrimidine 1643543-89-8 C6HBrD6N2
5-Bromo-4-(sec-butyl-d9)-pyrimidine 5-Bromo-4-(sec-butyl-d9)-pyrimidine 1643564-47-9 C8H11BrN2
5-Bromo-4-chloro-2-(methoxy-d3)-pyrimidine 5-Bromo-4-chloro-2-(methoxy-d3)-pyrimidine 1643579-54-7 C5H4BrClN2O
6-(iso-Propyl-d7)-pyridine-2-boronic acid pinacol ester 6-(iso-Propyl-d7)-pyridine-2-boronic acid pinacol ester 2223027-44-7 C14H22BNO2
3-(5-PIPERIDIN-4-YL-1,2,4-OXADIAZOL-3-YL)PYRIDINE 3-(5-PIPERIDIN-4-YL-1,2,4-OXADIAZOL-3-YL)PYRIDINE 114474-26-9 C9H7N3O2
2,2,6-Trimethyl-4H-1,3-dioxin-4-one 2,2,6-Trimethyl-4H-1,3-dioxin-4-one 5394-63-8 C7H10O3
4-Bromo-1-chloro-2-nitrobenzene 4-Bromo-1-chloro-2-nitrobenzene 16588-24-2 C6H3BrClNO2
1,5-DIMETHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE 1,5-DIMETHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE 79080-31-2 C6H7F3N2
4-(BROMOMETHYL)ISOXAZOLE 4-(BROMOMETHYL)ISOXAZOLE 6455-40-9 C4H4BrNO
4-chloro-7-(2-methoxyethoxy)quinazoline 4-chloro-7-(2-methoxyethoxy)quinazoline 199327-54-3 C11H11ClN2O2
2-Isopropyl-4-(methylaminomethyl)thiazole 2-Isopropyl-4-(methylaminomethyl)thiazole 154212-60-9 C8H14N2S
2-methyl-6-morpholin-4-yl-1H-pyrimidin-4-one 2-methyl-6-morpholin-4-yl-1H-pyrimidin-4-one 372171-74-9 C9H13N3O2
6-BROMO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID 6-BROMO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID 19075-58-2 C9H5BrO2S
2-Tetrahydrofuranyl methacrylate 2-Tetrahydrofuranyl methacrylate 15895-80-4 C8H12O3
Ethyl 4-iodo-1H-imidazole-2-carboxylate Ethyl 4-iodo-1H-imidazole-2-carboxylate 1824103-80-1 C6H7IN2O2
4-(2-THIAZOLYL)PHENOL 4-(2-THIAZOLYL)PHENOL 81015-49-8 C9H7NOS
2-AMINO-6-(4-PYRIDYL)PYRAZINE 2-AMINO-6-(4-PYRIDYL)PYRAZINE 1159814-77-3 C9H8N4
5-METHOXY-2,3-DIHYDRO-1H-ISOINDOLE 5-METHOXY-2,3-DIHYDRO-1H-ISOINDOLE 127168-88-1 C9H11NO
2,4-dichloro-6-(6'-bromo-2'-pyridyl)pyrimidine 2,4-dichloro-6-(6'-bromo-2'-pyridyl)pyrimidine 1185306-26-6 C9H4BrCl2N3
7-chloro-3H,4H-thieno[3,4-d]pyrimidin-4-one 7-chloro-3H,4H-thieno[3,4-d]pyrimidin-4-one 53826-83-8 C6H3ClN2OS
4-IODO-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 4-IODO-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 281204-89-5 C10H16INO2
(2-(2-fluorophenyl)pyrimidin-5-yl)boronic acid (2-(2-fluorophenyl)pyrimidin-5-yl)boronic acid 2225172-10-9 C10H8BFN2O2
(2-(3-chlorophenyl)pyrimidin-5-yl)boronic acid (2-(3-chlorophenyl)pyrimidin-5-yl)boronic acid 2225177-68-2 C10H8BClN2O2
(2-(ethoxy-d5)pyridin-4-yl)boronic acid (2-(ethoxy-d5)pyridin-4-yl)boronic acid 2241875-90-9 C7H5BD5NO3
(2-(furan-3-yl)pyridin-4-yl)boronic acid (2-(furan-3-yl)pyridin-4-yl)boronic acid 2225172-80-3 C9H8BNO3
(2-(o-tolyl)pyrimidin-5-yl)boronic acid (2-(o-tolyl)pyrimidin-5-yl)boronic acid 2225180-46-9 C11H11BN2O2
(2-(piperidin-3-yl)pyridin-4-yl)boronic acid (2-(piperidin-3-yl)pyridin-4-yl)boronic acid 2225151-78-8 C10H15BN2O2
(2-(tetrahydrofuran-3-yl)pyridin-4-yl)boronic acid (2-(tetrahydrofuran-3-yl)pyridin-4-yl)boronic acid 2225152-91-8 C9H12BNO3
(2-fluoro-6-(methyl-d3)pyridin-4-yl)boronic acid (2-fluoro-6-(methyl-d3)pyridin-4-yl)boronic acid 2241875-92-1 C6H7BFNO2
(5-(piperidin-3-yl)pyridin-3-yl)boronic acid (5-(piperidin-3-yl)pyridin-3-yl)boronic acid 2225153-08-0 C10H15BN2O2
(5-(sec-butyl)pyridin-3-yl)boronic acid (5-(sec-butyl)pyridin-3-yl)boronic acid 2225152-50-9 C9H14BNO2
(5-cyclohexylpyridin-3-yl)boronic acid (5-cyclohexylpyridin-3-yl)boronic acid 2225155-94-0 C11H16BNO2
1-(2-Pyridyl)-1H-pyrazole-4-boronic acid 1-(2-Pyridyl)-1H-pyrazole-4-boronic acid 1983203-12-8 C8H8BN3O2
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