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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
6-(2-Methyl-1H-imidazol-1-yl)pyrimidin-4-amine 6-(2-Methyl-1H-imidazol-1-yl)pyrimidin-4-amine 1314353-51-9 C8H9N5
7-Bromo-2,4-dichloropyrido[3,2-d]pyrimidine 7-Bromo-2,4-dichloropyrido[3,2-d]pyrimidine 1215074-41-1 C7H2BrCl2N3
Chloro[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]gold(I) Chloro[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]gold(I) 852445-82-0 C21H26AuClN2
5-cyclobutylpyridin-2-amine 5-cyclobutylpyridin-2-amine 1159814-97-7 C9H12N2
4-(4-chlorophenyl)pyridin-2-amine 4-(4-chlorophenyl)pyridin-2-amine 907945-72-6 C11H9ClN2
4-Bromo-1,2-dimethyl-1H-benzo[d]imidazole 4-Bromo-1,2-dimethyl-1H-benzo[d]imidazole 1379361-12-2 C9H9BrN2
6-BROMO-2-CHLOROOXAZOLO[5,4-B]PYRIDINE 6-BROMO-2-CHLOROOXAZOLO[5,4-B]PYRIDINE 1782797-89-0 C6H2BrClN2O
1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-2-one 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-2-one 1003309-09-8 C16H22BNO3
2-[(5-bromo-2-fluorophenyl)Methyl]-Benzo[b]thiophene 2-[(5-bromo-2-fluorophenyl)Methyl]-Benzo[b]thiophene 1034305-31-1 C15H10FIS
2-(1H-Pyrazol-1-yl)-5-(trifluoromethyl)pyrimidine 2-(1H-Pyrazol-1-yl)-5-(trifluoromethyl)pyrimidine 1398504-38-5 C8H5F3N4
(2-(thiazol-5-yl)pyridin-4-yl)boronic acid (2-(thiazol-5-yl)pyridin-4-yl)boronic acid 2225155-00-8 C8H7BN2O2S
2-(2-fluorophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(2-fluorophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 1402172-79-5 C17H19BFNO2
2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4'-bipyridine 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,4'-bipyridine 2223043-21-6 C16H19BN2O2
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(3-(trifluoromethyl)phenyl)pyridine 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(3-(trifluoromethyl)phenyl)pyridine 1402233-62-8 C18H19BF3NO2
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-ol 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-ol 2223012-50-6 C11H16BNO3
2-(tetrahydrofuran-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(tetrahydrofuran-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2222996-27-0 C15H22BNO3
2-cyclopentyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-cyclopentyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223037-41-8 C16H24BNO2
4-(1H-pyrazol-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(1H-pyrazol-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223050-94-8 C14H18BN3O2
4-(2-chlorophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(2-chlorophenyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223035-78-5 C17H19BClNO2
4-(4-methyl-1H-pyrazol-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(4-methyl-1H-pyrazol-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 1402240-23-6 C15H20BN3O2
4-(cyclohexyloxy)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-(cyclohexyloxy)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 1402174-16-6 C17H26BNO3
4-cyclohexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-cyclohexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 1402240-77-0 C17H26BNO2
4-isobutyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 4-isobutyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223053-41-4 C15H24BNO2
5-(3-methylpiperidin-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(3-methylpiperidin-1-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 1402174-01-9 C17H27BN2O2
5-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidine 5-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidine 2223036-40-4 C15H18BN3O2
5-cyclobutoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-cyclobutoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223045-27-8 C15H22BNO3
N,N-diethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-amine N,N-diethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-amine 1416063-41-6 C15H25BN2O2
tert-butyl 2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)morpholine-4-carboxylate tert-butyl 2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)morpholine-4-carboxylate 2223006-90-2 C20H31BN2O5
YQBLDZMARIUXJI-UHFFFAOYSA-N YQBLDZMARIUXJI-UHFFFAOYSA-N 1215537-40-8 C28H37N3O3
FHMKYTDEGLFVSL-UHFFFAOYSA-N FHMKYTDEGLFVSL-UHFFFAOYSA-N 76182-29-1 C6H7ClN2O2
(S)-Pyrrolidine-2-carbonitrile hydrochloride (S)-Pyrrolidine-2-carbonitrile hydrochloride 65732-69-6 C5H9ClN2
5-(furan-2-yl)pyridin-3-amine 5-(furan-2-yl)pyridin-3-amine 1314356-21-2 C9H8N2O
8-bromo-2-chloroimidazo[1,2-a]pyridine 8-bromo-2-chloroimidazo[1,2-a]pyridine 1260902-12-2 C7H4BrClN2
4-HYDROXYMETHYL-5-METHYLIMIDAZOLE 4-HYDROXYMETHYL-5-METHYLIMIDAZOLE 29636-87-1 C5H8N2O
6-(4-(trifluoromethyl)phenyl)pyridazin-3(2H)-one 6-(4-(trifluoromethyl)phenyl)pyridazin-3(2H)-one 66548-87-6 C11H7F3N2O
5-(Trifluoromethyl)indole 5-(Trifluoromethyl)indole 100846-24-0 C9H6F3N
5-bromo-2-(4-methylpyrazol-1-yl)pyrimidine 5-bromo-2-(4-methylpyrazol-1-yl)pyrimidine 1260896-61-4 C8H7BrN4
4-Isopropoxy-pyridin-3-ylamine 4-Isopropoxy-pyridin-3-ylamine 173435-38-6 C8H12N2O
CHEMBRDG-BB 4010221 CHEMBRDG-BB 4010221 6857-34-7 C9H8N2S
N-CYANOACETYLPYRROLIDINE N-CYANOACETYLPYRROLIDINE 14227-95-3 C7H10N2O
4,6-Dichloro-2-cyclopentyl-pyrimidine 4,6-Dichloro-2-cyclopentyl-pyrimidine 1353854-57-5 C9H10Cl2N2
3-Bromo-1-propyl-1H-pyrazole 3-Bromo-1-propyl-1H-pyrazole 1354706-10-7 C6H9BrN2
3-Bromo-2-cyclopentyloxy-pyridin-4-ylamine 3-Bromo-2-cyclopentyloxy-pyridin-4-ylamine 1563529-43-0 C10H13BrN2O
1-Methylindole 1-Methylindole 603-76-9 C9H9N
4-(MORPHOLINOMETHYL)BENZYLAMINE 4-(MORPHOLINOMETHYL)BENZYLAMINE 91271-84-0 C12H18N2O
2,3,5,6-tetradeuterio-4-nitro-1-oxidopyridin-1-ium 2,3,5,6-tetradeuterio-4-nitro-1-oxidopyridin-1-ium 119673-94-8 C5D4N2O3
2-(cyclopentyloxy)pyridin-4-amine 2-(cyclopentyloxy)pyridin-4-amine 1247459-58-0 C10H14N2O
1-(pyrimidin-4-yl)azetidin-3-ol 1-(pyrimidin-4-yl)azetidin-3-ol 1339651-68-1 C7H9N3O
5-Chloro-1-(4-piperidyl)-2-benzimidazolinone 5-Chloro-1-(4-piperidyl)-2-benzimidazolinone 53786-28-0 C12H14ClN3O
(6-Methyl-thieno[2,3-d]pyrimidin-4-yl)-hydrazine (6-Methyl-thieno[2,3-d]pyrimidin-4-yl)-hydrazine 439692-69-0 C7H8N4S
4,4'-Trimethylenebis(1-methylpiperidine) 4,4'-Trimethylenebis(1-methylpiperidine) 64168-11-2 C15H30N2
(6-Methyl-5-ethyl-d8)-pyridine-3-boronic acid (6-Methyl-5-ethyl-d8)-pyridine-3-boronic acid 2225180-37-8 C8H12BNO2
[2-(tert-Butyl)-3-methyl-d12]-pyridine-4-boronic acid [2-(tert-Butyl)-3-methyl-d12]-pyridine-4-boronic acid 2225179-78-0 C10H16BNO2
[4-Methyl-6-(iso-butyl)-d12]-pyridine-3-boronic acid [4-Methyl-6-(iso-butyl)-d12]-pyridine-3-boronic acid 2225168-99-8 C10H16BNO2
[5-Methyl-6-(iso-propyl)-d10]-pyridine-3-boronic acid [5-Methyl-6-(iso-propyl)-d10]-pyridine-3-boronic acid 2225176-28-1 C9H14BNO2
[6-Methyl-5-(iso-propyl)-d10]-pyridine-3-boronic acid [6-Methyl-5-(iso-propyl)-d10]-pyridine-3-boronic acid 2225169-02-6 C9H14BNO2
2-(n-Propyl-d7)-pyrimidine-5-boronic acid 2-(n-Propyl-d7)-pyrimidine-5-boronic acid 2225171-87-7 C7H11BN2O2
2-(Pyrrolidinopyridine-d11)-4-boronic acid 2-(Pyrrolidinopyridine-d11)-4-boronic acid 2225172-30-3 C9H13BN2O2
2-Amino-4-(iso-butyl-d9)-pyridine 2-Amino-4-(iso-butyl-d9)-pyridine 1643539-25-6 C9H14N2
2-Amino-4-(sec-butyl-d9)-pyridine 2-Amino-4-(sec-butyl-d9)-pyridine 1643562-59-7 C9H14N2
2-Amino-5-(ethyl-d5)-pyridine 2-Amino-5-(ethyl-d5)-pyridine 1185311-20-9 C7H10N2
2-Amino-5-(n-propoxy-d7)-pyridine 2-Amino-5-(n-propoxy-d7)-pyridine 1643577-00-7 C8H12N2O
2-Amino-5-(piperidino-d10)-pyridine 2-Amino-5-(piperidino-d10)-pyridine 1643542-11-3 C10H15N3
2-Amino-6-(iso-propyl-d7)-pyridine 2-Amino-6-(iso-propyl-d7)-pyridine 1185313-64-7 C8H12N2
2-Bromo-3,5-(d-methyl-d6)-4-(methoxy-d3)-pyridine 2-Bromo-3,5-(d-methyl-d6)-4-(methoxy-d3)-pyridine 1185313-47-6 C8H10BrNO
2-Bromo-4-(methoxy-d3)-pyridine 2-Bromo-4-(methoxy-d3)-pyridine 1185310-54-6 C6H6BrNO
2-Bromo-4-(methylethylamino)pyridine-d11 2-Bromo-4-(methylethylamino)pyridine-d11 1643537-82-9 C8H11BrN2
2-Bromo-4-chloropyridine-d3 2-Bromo-4-chloropyridine-d3 1643575-67-0 C5H3BrClN
2-Bromo-5-(iso-propoxy)pyridine-d10 2-Bromo-5-(iso-propoxy)pyridine-d10 1643562-56-4 C8H10BrNO
2-Bromo-5-(pyrrolidino-d8)-pyridine 2-Bromo-5-(pyrrolidino-d8)-pyridine 1643563-74-9 C9H11BrN2
2-Bromo-5-aminopyridine-3,4,6-d3 2-Bromo-5-aminopyridine-3,4,6-d3 1643543-84-3 C5H5BrN2
2-Bromo-5-morpholinopyridine-d11 2-Bromo-5-morpholinopyridine-d11 1374664-33-1 C9H11BrN2O
2-Bromo-6-(iso-propyl)pyridine-d10 2-Bromo-6-(iso-propyl)pyridine-d10 1643575-75-0 C8H10BrN
2-Bromo-6-(n-propoxy-d7)-pyridine 2-Bromo-6-(n-propoxy-d7)-pyridine 1185312-62-2 C8H3BrD7NO
2-Bromo-6-(phenyl-d5)-pyridine 2-Bromo-6-(phenyl-d5)-pyridine 1185319-01-0 C11H8BrN
2-Bromo-6-[N-Boc-(piperazin-d8)-1-yl]pyridine 2-Bromo-6-[N-Boc-(piperazin-d8)-1-yl]pyridine 1643541-74-5 C14H20BrN3O2
2-Chloro-4-(Methoxy-d3)-pyrimidine 2-Chloro-4-(Methoxy-d3)-pyrimidine 1215072-03-9 C5H5ClN2O
2-Chloro-6-(iso-butyl-d9)-pyridine-4-boronic acid 2-Chloro-6-(iso-butyl-d9)-pyridine-4-boronic acid 2225155-92-8 C9H13BClNO2
2-Cyano-6-(tert-butyl-d9)-pyridine-4-boronic acid 2-Cyano-6-(tert-butyl-d9)-pyridine-4-boronic acid 2225170-65-8 C10H13BN2O2
2-Hydroxy-4-(ethyl-d5)-pyridine 2-Hydroxy-4-(ethyl-d5)-pyridine 1185313-96-5 C7H9NO
3-Acetyl-6-(methyl-d3)-pyridine 3-Acetyl-6-(methyl-d3)-pyridine 1185314-07-1 C8H6D3NO
3-Amino-6-(ethyl-d5)-pyridine 3-Amino-6-(ethyl-d5)-pyridine 1185317-37-6 C7H10N2
3-Amino-6-(iso-propyl-d7)-pyridine 3-Amino-6-(iso-propyl-d7)-pyridine 1185309-04-9 C8H12N2
3-Amino-6-bromopyridazine-4,5-d2 3-Amino-6-bromopyridazine-4,5-d2 1643579-73-0 C4H4BrN3
3-Bromo-[2-methyl-5-(iso-butyl)-d12]-pyridine 3-Bromo-[2-methyl-5-(iso-butyl)-d12]-pyridine 1643538-54-8 C10H14BrN
3-Bromo-[5-methyl-6-(iso-butyl)-d12]-pyridine 3-Bromo-[5-methyl-6-(iso-butyl)-d12]-pyridine 1643537-97-6 C10H14BrN
3-Bromo-[6-(sec-butyl)-4-methyl-d12]-pyridine 3-Bromo-[6-(sec-butyl)-4-methyl-d12]-pyridine 1643537-91-0 C10H14BrN
3-Bromo-2-(methyl-d3)-pyridine 3-Bromo-2-(methyl-d3)-pyridine 1185314-16-2 C6H6BrN
3-Bromo-2-methyl-6-(methoxy-d3)-pyridine 3-Bromo-2-methyl-6-(methoxy-d3)-pyridine 1185319-83-8 C7H5BrD3NO
3-Bromo-5-(iso-propyl)pyridine-d10 3-Bromo-5-(iso-propyl)pyridine-d10 1643537-92-1 C8BrD10N
3-Bromo-5-(pyrrolidino)pyridine-d11 3-Bromo-5-(pyrrolidino)pyridine-d11 1643577-04-1 C9BrD11N2
3-Bromo-5-(tert-butoxy)pyridine-d12 3-Bromo-5-(tert-butoxy)pyridine-d12 1643576-22-0 C9H12BrNO
3-Bromo-5-methyl-6-(methoxy-d3)-pyridine 3-Bromo-5-methyl-6-(methoxy-d3)-pyridine 1185317-02-5 C7H8BrNO
3-Bromo-6-(diethylamino)pyridazine-d12 3-Bromo-6-(diethylamino)pyridazine-d12 1643544-00-6 C8H12BrN3
3-Bromo-6-(iso-propoxy)pyridazine-d9 3-Bromo-6-(iso-propoxy)pyridazine-d9 1643575-51-2 C7H9BrN2O
3-Bromo-6-(iso-propyl)pyridine-d10 3-Bromo-6-(iso-propyl)pyridine-d10 1643563-59-0 C8H10BrN
3-Bromo-6-(morpholino-d8)-pyridine 3-Bromo-6-(morpholino-d8)-pyridine 1643542-99-7 C9H11BrN2O
3-Bromo-6-(n-propyl)pyridazine-d9 3-Bromo-6-(n-propyl)pyridazine-d9 1643539-42-7 C7H9BrN2
3-Bromo-6-(tert-butoxy)pyridazine-d11 3-Bromo-6-(tert-butoxy)pyridazine-d11 1643537-65-8 C8H11BrN2O
3-Bromo-6-(tert-butyl-d9)-pyridine 3-Bromo-6-(tert-butyl-d9)-pyridine 1643539-11-0 C9H12BrN
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