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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-4-(tert-butoxy-d9)-pyridine 2-Amino-4-(tert-butoxy-d9)-pyridine 1643542-35-1 C9H14N2O
2-Amino-5-(iso-propoxy-d7)-pyridine 2-Amino-5-(iso-propoxy-d7)-pyridine 1643562-88-2 C8H12N2O
2-Amino-5-(n-propyl)pyridine-d10 2-Amino-5-(n-propyl)pyridine-d10 1643542-27-1 C8H12N2
2-Amino-6-(ethyl-d5)-pyridine 2-Amino-6-(ethyl-d5)-pyridine 1185315-15-4 C7H10N2
2-Bromo-4-(ethoxy-d5-carbonyl)-pyridine 2-Bromo-4-(ethoxy-d5-carbonyl)-pyridine 1643564-55-9 C8H8BrNO2
2-Bromo-4-(methylethylamino-d8)-pyridine 2-Bromo-4-(methylethylamino-d8)-pyridine 1643564-32-2 C8H3BrD8N2
2-Bromo-4-(n-propyl)pyridine-d10 2-Bromo-4-(n-propyl)pyridine-d10 1643563-48-7 C8BrD10N
2-Bromo-4-cyanopyridine-d3 2-Bromo-4-cyanopyridine-d3 1643575-84-1 C6H3BrN2
2-Bromo-4-fluoropyridine-d3 2-Bromo-4-fluoropyridine-d3 1643539-27-8 C5H3BrFN
2-Bromo-5-(n-propoxy)pyridine-d10 2-Bromo-5-(n-propoxy)pyridine-d10 1643541-87-0 C8H10BrNO
2-Bromo-5-(piperidino-d10)-pyridine 2-Bromo-5-(piperidino-d10)-pyridine 1643575-40-9 C10H13BrN2
2-Bromo-5-(tert-butyl-d9)-pyridine 2-Bromo-5-(tert-butyl-d9)-pyridine 1643562-90-6 C9H3BrD9N
2-Bromo-5-chloropyridine-d3 2-Bromo-5-chloropyridine-d3 1643576-61-7 C5H3BrClN
2-Bromo-5-trifluoromethylpyridine-d3 2-Bromo-5-trifluoromethylpyridine-d3 1643543-32-1 C6H3BrF3N
2-Bromo-6-(piperidin-4-yl)pyridine-d8 2-Bromo-6-(piperidin-4-yl)pyridine-d8 1622842-84-5 C10H13BrN2
2-Bromo-6-(tert-butyl-d9)-pyridine 2-Bromo-6-(tert-butyl-d9)-pyridine 1643577-61-0 C9H12BrN
2-Bromo-6-[N-Boc-(pyridine-3,4,5-d3)] 2-Bromo-6-[N-Boc-(pyridine-3,4,5-d3)] 1643541-83-6 C15H21BrN2O4
2-Bromo-6-methylpyridine-d6 2-Bromo-6-methylpyridine-d6 1374664-32-0 C6H6BrN
2-Chloro-4-(methyl-13C, d3)pyrimidine 2-Chloro-4-(methyl-13C, d3)pyrimidine 1227958-88-4 C5H2ClD3N2
2-Chloro-6-(iso-propyl-d7)-4-aminopyridine 2-Chloro-6-(iso-propyl-d7)-4-aminopyridine 1185312-74-6 C8H4ClD7N2
3-Amino-2-(methyl-d3)-pyridine 3-Amino-2-(methyl-d3)-pyridine 1185313-55-6 C6H5D3N2
3-Amino-5-(methyl-d3)-pyridine 3-Amino-5-(methyl-d3)-pyridine 1185320-01-7 C6H8N2
3-Amino-6-(methoxy-d3)-pyridazine 3-Amino-6-(methoxy-d3)-pyridazine 1643544-01-7 C5H7N3O
3-Amino-6-(n-propoxy-d7)-pyridazine 3-Amino-6-(n-propoxy-d7)-pyridazine 1643576-92-4 C7H11N3O
3-Bromo-(4,6-dimethyl-d6)-pyridine 3-Bromo-(4,6-dimethyl-d6)-pyridine 1643538-82-2 C7H8BrN
3-Bromo-[2-methyl-5-(n-propyl)-d10]-pyridine 3-Bromo-[2-methyl-5-(n-propyl)-d10]-pyridine 1643542-91-9 C9H12BrN
3-Bromo-[2-methyl-5-(tert-butyl)-d12]-pyridine 3-Bromo-[2-methyl-5-(tert-butyl)-d12]-pyridine 1643543-13-8 C10H14BrN
3-Bromo-[5-methyl-6-(iso-propyl)-d10]-pyridine 3-Bromo-[5-methyl-6-(iso-propyl)-d10]-pyridine 1643562-78-0 C9H12BrN
3-Bromo-[6-methyl-5-(iso-butyl)-d12]-pyridine 3-Bromo-[6-methyl-5-(iso-butyl)-d12]-pyridine 1643577-42-7 C10H14BrN
3-Bromo-2-methyl-6-(methyl-d3)-pyridine 3-Bromo-2-methyl-6-(methyl-d3)-pyridine 1185310-79-5 C7H8BrN
3-Bromo-5-(methyl-d3)-pyridine 3-Bromo-5-(methyl-d3)-pyridine 1185314-90-2 C6H6BrN
3-Bromo-5-(tert-butoxy-d9)-pyridine 3-Bromo-5-(tert-butoxy-d9)-pyridine 1643543-15-0 C9H3BrD9NO
3-Bromo-5-methyl-6-(methyl-d3)-pyridine 3-Bromo-5-methyl-6-(methyl-d3)-pyridine 1185319-79-2 C7H8BrN
3-Bromo-6-(diethylamino-d10)-pyridazine 3-Bromo-6-(diethylamino-d10)-pyridazine 1643538-95-7 C8H12BrN3
3-Bromo-6-(iso-propoxy)pyridine-d10 3-Bromo-6-(iso-propoxy)pyridine-d10 1643537-85-2 C8BrD10NO
3-Bromo-6-(iso-propyl-d7)-pyridazine 3-Bromo-6-(iso-propyl-d7)-pyridazine 1185314-94-6 C7H9BrN2
3-Bromo-6-(n-propoxy)pyridazine-d9 3-Bromo-6-(n-propoxy)pyridazine-d9 1643544-08-4 C7H9BrN2O
3-Bromo-6-(n-propyl)pyridine-d10 3-Bromo-6-(n-propyl)pyridine-d10 1643577-66-5 C8H10BrN
3-Bromo-6-(tert-butoxy-d9)-pyridazine 3-Bromo-6-(tert-butoxy-d9)-pyridazine 1185318-44-8 C8H11BrN2O
3-Bromo-6-[(N-methylpiperazin-d11)-1-yl]-pyridazine 3-Bromo-6-[(N-methylpiperazin-d11)-1-yl]-pyridazine 1643542-56-6 C9H13BrN4
3-Chloro-4-methyl-6-(ethyl-d5)-pyridazine 3-Chloro-4-methyl-6-(ethyl-d5)-pyridazine 1185306-61-9 C7H9ClN2
3-Iodo-5-bromopyridine-2,4,6-d3 3-Iodo-5-bromopyridine-2,4,6-d3 1643562-67-7 C5BrD3IN
4-(Dimethylamino-d6)-pyridine-2-boronic acid pinacol ester 4-(Dimethylamino-d6)-pyridine-2-boronic acid pinacol ester 2223035-37-6 C13H21BN2O2
4,6-Dichloro-2-(ethyl-d5)-pyrimidine 4,6-Dichloro-2-(ethyl-d5)-pyrimidine 1185317-56-9 C6H6Cl2N2
4-Amino-2-(ethyl-d5)-pyridine 4-Amino-2-(ethyl-d5)-pyridine 1185317-77-4 C7H5D5N2
4-Bromo-[2-methyl-6-(iso-propyl)-d10]-pyridine 4-Bromo-[2-methyl-6-(iso-propyl)-d10]-pyridine 1643537-44-3 C9H12BrN
4-Bromo-2-(cyano-13C, 15N)thiazole 4-Bromo-2-(cyano-13C, 15N)thiazole 1227958-91-9 C4HBrN2S
4-Bromo-2-(ethyl-d5)-pyrimidine 4-Bromo-2-(ethyl-d5)-pyrimidine 1185309-70-9 C6H7BrN2
4-Bromo-2-(iso-propyl-d7-amino)pyridine 4-Bromo-2-(iso-propyl-d7-amino)pyridine 1185313-11-4 C8H11BrN2
4-Bromo-2-(n-propyl-d7)-6-trifluoromethylpyridine 4-Bromo-2-(n-propyl-d7)-6-trifluoromethylpyridine 1643563-33-0 C9H9BrF3N
4-Bromo-2-(sec-butyl)pyridine-d12 4-Bromo-2-(sec-butyl)pyridine-d12 1643538-07-1 C9H12BrN
4-Bromo-2-(sec-butyl-d9)-6-trifluoromethylpyridine 4-Bromo-2-(sec-butyl-d9)-6-trifluoromethylpyridine 1643542-74-8 C10H11BrF3N
4-Bromo-2-[(piperazin-1-yl)pyridine-d11] 4-Bromo-2-[(piperazin-1-yl)pyridine-d11] 1643564-31-1 C9H12BrN3
4-Bromo-2-chloro-6-(iso-butyl-d9)-pyridine 4-Bromo-2-chloro-6-(iso-butyl-d9)-pyridine 1643564-13-9 C9H11BrClN
4-Bromo-2-ethylpyridine-d8 4-Bromo-2-ethylpyridine-d8 1643563-41-0 C7BrD8N
4-Bromo-2-fluoro-6-(methyl-d3)-pyridine 4-Bromo-2-fluoro-6-(methyl-d3)-pyridine 1643563-00-1 C6H5BrFN
4-Bromo-6-(methoxy-d3)-pyrimidine 4-Bromo-6-(methoxy-d3)-pyrimidine 1185318-17-5 C5H5BrN2O
4-Chloro-2-amino-6-(n-propyl-d7)-pyrimidine 4-Chloro-2-amino-6-(n-propyl-d7)-pyrimidine 1185315-12-1 C7H3ClD7N3
4-Chloro-5-cyano-2-(iso-propyl-d7)-pyrimidine 4-Chloro-5-cyano-2-(iso-propyl-d7)-pyrimidine 1185309-78-7 C8H8ClN3
4-Chloro-5-trifluoromethyl-2-(iso-propyl-d7)-pyrimidine 4-Chloro-5-trifluoromethyl-2-(iso-propyl-d7)-pyrimidine 1185312-06-4 C8H8ClF3N2
4-Chloro-6-(methyl-d3)-pyrimidine 4-Chloro-6-(methyl-d3)-pyrimidine 1185318-23-3 C5H5ClN2
5-(Ethyl-d5)-pyridine-2-boronic acid pinacol ester 5-(Ethyl-d5)-pyridine-2-boronic acid pinacol ester 2223045-83-6 C13H20BNO2
5-(iso-Propyl-d7)-pyridine-2-boronic acid pinacol ester 5-(iso-Propyl-d7)-pyridine-2-boronic acid pinacol ester 2223052-37-5 C14H22BNO2
5-(Pyrrolidinopyridine-d11)-2-boronic acid pinacol ester 5-(Pyrrolidinopyridine-d11)-2-boronic acid pinacol ester 2223032-41-3 C15H23BN2O2
5-[(iso-Propyl)pyridine-d10]-2-boronic acid pinacol ester 5-[(iso-Propyl)pyridine-d10]-2-boronic acid pinacol ester 2223038-83-1 C14H22BNO2
5-Bromo-2-(methyl-d3)-pyrimidine 5-Bromo-2-(methyl-d3)-pyrimidine 1185316-89-5 C5H5BrN2
5-Bromo-2-(sec-butyl-d9)-pyrimidine 5-Bromo-2-(sec-butyl-d9)-pyrimidine 1643577-54-1 C8H2BrD9N2
5-Bromo-4-(ethyl-d5)-pyrimidine 5-Bromo-4-(ethyl-d5)-pyrimidine 1643539-15-4 C6H7BrN2
6-(2-Furyl)(pyridine-d3)-2-boronic acid pinacol ester 6-(2-Furyl)(pyridine-d3)-2-boronic acid pinacol ester 2223040-03-5 C15H18BNO3
6-(3-Furyl)(pyridine-d3)-2-boronic acid pinacol ester 6-(3-Furyl)(pyridine-d3)-2-boronic acid pinacol ester 2223032-08-2 C15H18BNO3
5-BROMO-2,3-DIHYDROSPIRO[IMIDAZOLIDINE-4,1-INDENE]-2,5-DIONE 5-BROMO-2,3-DIHYDROSPIRO[IMIDAZOLIDINE-4,1-INDENE]-2,5-DIONE 553680-99-2 C11H9BrN2O2
4-Bromo-3,5-dimethylpyrazole 4-Bromo-3,5-dimethylpyrazole 3398-16-1 C5H7BrN2
2-CHLORO-1H-INDOLE-3-CARBALDEHYDE 2-CHLORO-1H-INDOLE-3-CARBALDEHYDE 5059-30-3 C9H6ClNO
4-Bromo-1H-indazole 4-Bromo-1H-indazole 186407-74-9 C7H5BrN2
2,3-Dihydrofuran 2,3-Dihydrofuran 1191-99-7 C4H6O
4-(1H-IMIDAZOL-4-YLMETHYL)PIPERIDINE DIHYDROBROMIDE 4-(1H-IMIDAZOL-4-YLMETHYL)PIPERIDINE DIHYDROBROMIDE 164391-47-3 C9H17Br2N3
(3R,4R)-(-)-1-BENZYL-3,4-PYRROLIDINDIOL (3R,4R)-(-)-1-BENZYL-3,4-PYRROLIDINDIOL 76784-33-3 C11H15NO2
3,6-dimethoxythieno[3,2-b]thiophene 3,6-dimethoxythieno[3,2-b]thiophene 850233-79-3 C8H8O2S2
2,3,6-Trimethylimidazo[2,1-b]thiazole-5-carboxylic acid 2,3,6-Trimethylimidazo[2,1-b]thiazole-5-carboxylic acid 1007875-80-0 C9H10N2O2S
4-Aminothieno[2,3-d]pyrimidine-6-carbaldehyde 4-Aminothieno[2,3-d]pyrimidine-6-carbaldehyde 655254-90-3 C7H5N3OS
6'-Bromo-8'-methyl-1'H-spiro[cyclopentane-1,3'-imidazo[1,5-a]pyridine]-1',5'(2'H)-dione 6'-Bromo-8'-methyl-1'H-spiro[cyclopentane-1,3'-imidazo[1,5-a]pyridine]-1',5'(2'H)-dione 1849592-55-7 C12H13BrN2O2
1-bromo-7,7-dimethyl-7H-fluoreno[2,3-b]benzofuran 1-bromo-7,7-dimethyl-7H-fluoreno[2,3-b]benzofuran 2217688-31-6 C21H15BrO
4-cyclopropylpyrimidin-2(1H)-one 4-cyclopropylpyrimidin-2(1H)-one 1215071-65-0 C7H8N2O
5,5'-(2,5-Bis(2-ethylhexyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(thiophene-2-carbaldehyde) 5,5'-(2,5-Bis(2-ethylhexyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(thiophene-2-carbaldehyde) 1239218-96-2 C32H40N2O4S2
2,3-BENZOCARBAZOLE 2,3-BENZOCARBAZOLE 243-28-7 C16H11N
5-bromo-2-(butan-2-yl)-4-chloropyrimidine 5-bromo-2-(butan-2-yl)-4-chloropyrimidine 1506786-09-9 C8H10BrClN2
{5H,6H,7H,8H-imidazo[1,2-a]pyridin-2-ylmethyl}(methyl)amine {5H,6H,7H,8H-imidazo[1,2-a]pyridin-2-ylmethyl}(methyl)amine 1500012-34-9 C9H15N3
2-(1-methyl-1H-pyrazol-4-yl)pyridin-3-amine 2-(1-methyl-1H-pyrazol-4-yl)pyridin-3-amine 1554842-76-0 C9H10N4
1H-1,2,3-TRIAZOLO[4,5-B]PYRIDINE 1H-1,2,3-TRIAZOLO[4,5-B]PYRIDINE 273-34-7 C5H4N4
(2-(2-(methyl-d3)propan-2-yl-1,1,1,3,3,3-d6)pyridin-4-yl)boronic acid (2-(2-(methyl-d3)propan-2-yl-1,1,1,3,3,3-d6)pyridin-4-yl)boronic acid 2241875-88-5 C9H5BD9NO2
(2-(2-chlorophenyl)pyrimidin-5-yl)boronic acid (2-(2-chlorophenyl)pyrimidin-5-yl)boronic acid 2225170-25-0 C10H8BClN2O2
(2-(bis(methyl-d3)amino)pyridin-4-yl)boronic acid (2-(bis(methyl-d3)amino)pyridin-4-yl)boronic acid 2241875-85-2 C7H11BN2O2
(2-(morpholino-d8)pyrimidin-5-yl)boronic acid (2-(morpholino-d8)pyrimidin-5-yl)boronic acid 2241877-04-1 C8H12BN3O3
(2-(pyridin-3-yl)pyrimidin-5-yl)boronic acid (2-(pyridin-3-yl)pyrimidin-5-yl)boronic acid 2225176-57-6 C9H8BN3O2
(2,3-bis(methyl-d3)pyridin-4-yl)boronic acid (2,3-bis(methyl-d3)pyridin-4-yl)boronic acid 2241875-98-7 C7H4BD6NO2
(4-(ethyl-d5)pyrimidin-5-yl)boronic acid (4-(ethyl-d5)pyrimidin-5-yl)boronic acid 2225175-58-4 C6H9BN2O2
(5-(methyl-d3)-6-(propyl-d7)pyridin-3-yl)boronic acid (5-(methyl-d3)-6-(propyl-d7)pyridin-3-yl)boronic acid 2241876-05-9 C9H14BNO2
(6-(piperidin-4-yl)pyridin-3-yl)boronic acid (6-(piperidin-4-yl)pyridin-3-yl)boronic acid 1448457-46-2 C10H15BN2O2
[2-(METHOXYCARBONYL)-6-IODOPYRIDIN-4-YL]BORONIC ACID [2-(METHOXYCARBONYL)-6-IODOPYRIDIN-4-YL]BORONIC ACID 2225154-49-2 C7H7BINO4
[2,4'-bipyrimidin]-5-ylboronic acid [2,4'-bipyrimidin]-5-ylboronic acid 2225172-40-5 C8H7BN4O2
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