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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
ethyl 7-(difluoromethyl)-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylate ethyl 7-(difluoromethyl)-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylate 438219-16-0 C16H13F2N3O2
9H-Dibenzo[a,c]carbazole 9H-Dibenzo[a,c]carbazole 201-67-2 C20H13N
3-Amino-4-methyl-4H-1,2,4-triazole 3-Amino-4-methyl-4H-1,2,4-triazole 16681-76-8 C3H6N4
2-CHLORO-5,6-DIMETHYLBENZIMIDAZOLE 2-CHLORO-5,6-DIMETHYLBENZIMIDAZOLE 39791-96-3 C9H9ClN2
2-(2-HYDROXYPHENYL)BENZOXAZOLE 2-(2-HYDROXYPHENYL)BENZOXAZOLE 835-64-3 C13H9NO2
2-(2,6-dioxopiperidin-3-yl)-5-(3-(hydroxymethyl)pyrrolidin-1-yl)isoindoline-1,3-dione 2-(2,6-dioxopiperidin-3-yl)-5-(3-(hydroxymethyl)pyrrolidin-1-yl)isoindoline-1,3-dione 2412058-47-8 C18H19N3O5
2-BROMO-4-IMIDAZOL-1-YL-PYRIDINE 2-BROMO-4-IMIDAZOL-1-YL-PYRIDINE 886363-89-9 C8H6BrN3
2(1H)-Pyridinone, 1-(2-methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2(1H)-Pyridinone, 1-(2-methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1598407-01-2 C14H22BNO4
2-Thiophenamine, 5-(4-pyridinyl)- 2-Thiophenamine, 5-(4-pyridinyl)- 692889-07-9 C9H8N2S
1H-1,2,3-Triazole, 5-(2-methylpropyl)- 1H-1,2,3-Triazole, 5-(2-methylpropyl)- 29143-31-5 C6H11N3
2-(1-TRITYL-1H-IMIDAZOL-4-YL)-ETHYLAMINE HYDRATE 2-(1-TRITYL-1H-IMIDAZOL-4-YL)-ETHYLAMINE HYDRATE 195053-92-0 C24H23N3
8-METHYL-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 8-METHYL-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 88751-05-7 C9H8N2O2
Pyrimidine, 4-chloro-6-(1H-imidazol-2-yl)- Pyrimidine, 4-chloro-6-(1H-imidazol-2-yl)- 943314-79-2 C7H5ClN4
1H-1,2,3-Triazole, 1-(1-methylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1H-1,2,3-Triazole, 1-(1-methylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2223027-39-0 C11H20BN3O2
5-Thiazolamine, 4-methyl-, hydrochloride (1:1) 5-Thiazolamine, 4-methyl-, hydrochloride (1:1) 168156-11-4 C4H7ClN2S
Pyridine-2,3,5,6-d4, 4-chloro-, 1-oxide Pyridine-2,3,5,6-d4, 4-chloro-, 1-oxide 1001003-90-2 C5H4ClNO
2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2819702-29-7 C12H18BNO2
2-(methyl-d2)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(methyl-d2)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2819702-45-7 C12H18BNO2
2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-4,5,6-d3 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-4,5,6-d3 2819702-89-9 C12H18BNO2
tert-butyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl-3,4,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 tert-butyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl-3,4,6-d3)piperidine-1-carboxylate-2,2,3,4,4,5,5,6,6-d9 2819703-40-5 C21H33BN2O4
tert-butyl 3-(6-(difluoromethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperidine-1-carboxylate tert-butyl 3-(6-(difluoromethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperidine-1-carboxylate 2819706-04-0 C22H33BF2N2O4
1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one-3,5,6-d3 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one-3,5,6-d3 2819705-07-0 C12H18BNO3
5-ethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline 5-ethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline 2819706-54-0 C16H21BN2O2
3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)tetrahydro-4H-pyran-4-one 3-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)tetrahydro-4H-pyran-4-one 2819707-04-3 C16H22BNO4
3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)tetrahydro-4H-pyran-4-one 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)tetrahydro-4H-pyran-4-one 2819707-19-0 C16H22BNO4
3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)tetrahydro-4H-pyran-4-one 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)tetrahydro-4H-pyran-4-one 2819707-24-7 C15H21BN2O4
methyl 2-cyano-5-cyclopropyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate methyl 2-cyano-5-cyclopropyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 2819707-76-9 C18H22BNO4
5-fluoro-4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 5-fluoro-4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 2819708-01-3 C14H17BFNO3
1H-Pyrazole-3-carboxylic acid, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, ethyl ester 1H-Pyrazole-3-carboxylic acid, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, ethyl ester 2711075-62-4 C12H19BN2O4
3-Pyridinamine, 5-cyclopropyl-6-methoxy- 3-Pyridinamine, 5-cyclopropyl-6-methoxy- 1354223-55-4 C9H12N2O
Pyrimidine, 4-(6-bromo-2-pyridinyl)- Pyrimidine, 4-(6-bromo-2-pyridinyl)- 1414851-18-5 C9H6BrN3
2,2'-Bioxazole, 4,4'-bis(4-fluorophenyl)-4,4',5,5'-tetrahydro-, (4S,4'S)- 2,2'-Bioxazole, 4,4'-bis(4-fluorophenyl)-4,4',5,5'-tetrahydro-, (4S,4'S)- 2567867-99-4 C18H14F2N2O2
Boronic acid, B-[2-(5-pyrimidinyl)phenyl]- Boronic acid, B-[2-(5-pyrimidinyl)phenyl]- 2225180-21-0 C10H9BN2O2
1-(4-BROMOBENZYL)-1H-IMIDAZOLE 1-(4-BROMOBENZYL)-1H-IMIDAZOLE 72459-46-2 C10H9BrN2
1H-1,2,4-Triazole, 3-bromo-5-methyl- 1H-1,2,4-Triazole, 3-bromo-5-methyl- 26557-90-4 C3H4BrN3
Reaction mass of 2-ethyl-4-methyl-1H-imidazole-1-propiononitrile and 2-ethyl-5-methyl-1H-imidazole-1-propiononitrile Reaction mass of 2-ethyl-4-methyl-1H-imidazole-1-propiononitrile and 2-ethyl-5-methyl-1H-imidazole-1-propiononitrile 568591-00-4
1-benzyltriazole 1-benzyltriazole 4368-68-7 C9H9N3
9-phenyl-1,7-diazabicyclo[4.3.0]nona-2,4,6,8-tetraene 9-phenyl-1,7-diazabicyclo[4.3.0]nona-2,4,6,8-tetraene 92961-15-4 C13H10N2
BIOTIN-NHS BIOTIN-NHS 35013-72-0 C14H19N3O5S
3,4,5,6-tetradeuteriopyridin-2-amine 3,4,5,6-tetradeuteriopyridin-2-amine 87802-54-8 C5H2D4N2
2-Cyclopropylthiazol-4-amine 2-Cyclopropylthiazol-4-amine 1159816-82-6 C6H8N2S
2-chloro-3-((tetrahydrofuran-3-yl)oxy)pyridine 2-chloro-3-((tetrahydrofuran-3-yl)oxy)pyridine 1497388-44-9 C9H10ClNO2
1-METHYL-4-(TRIFLUOROMETHYL)-1H-IMIDAZOLE-2-CARBOXYLIC ACID 1-METHYL-4-(TRIFLUOROMETHYL)-1H-IMIDAZOLE-2-CARBOXYLIC ACID 1554401-44-3 C6H5F3N2O2
N-BOC-4-Hydroxypiperidine N-BOC-4-Hydroxypiperidine 109384-19-2 C10H19NO3
4,5-DIPHENYL-2-MERCAPTOOXAZOLE 4,5-DIPHENYL-2-MERCAPTOOXAZOLE 6670-13-9 C15H11NOS
1-(4-Fluoro-phenyl)-1H-pyrazol-4-ol 1-(4-Fluoro-phenyl)-1H-pyrazol-4-ol 77458-31-2 C9H7FN2O
2-CHLOROADAMANTANE 2-CHLOROADAMANTANE 7346-41-0 C10H15Cl
3-(1H-1,2,3-TRIAZOL-4-YL)BENZONITRILE AND 3-(2H-1,2,3-TRIAZOL-4-YL)BENZONITRILE 3-(1H-1,2,3-TRIAZOL-4-YL)BENZONITRILE AND 3-(2H-1,2,3-TRIAZOL-4-YL)BENZONITRILE 550364-01-7 C9H6N4
(2S,4S)-4-Fluoro-2-(Fluoromethyl)Pyrrolidine Hydrochloride(WX601106) (2S,4S)-4-Fluoro-2-(Fluoromethyl)Pyrrolidine Hydrochloride(WX601106) 1951424-95-5 C5H10ClF2N
[2-(2-HYDROXYPROPAN-2-YL)PYRIDINE-d9]-4-BORONIC ACID [2-(2-HYDROXYPROPAN-2-YL)PYRIDINE-d9]-4-BORONIC ACID 2225173-28-2 C8H12BNO3
[2-Methyl-6-(n-propyl)-d10]-pyridine-4-boronic acid [2-Methyl-6-(n-propyl)-d10]-pyridine-4-boronic acid 2225176-42-9 C9H14BNO2
[5-Methyl-6-(sec-butyl)-d12]-pyridine-3-boronic acid [5-Methyl-6-(sec-butyl)-d12]-pyridine-3-boronic acid 2225153-23-9 C10H16BNO2
2-(Ethyl-d5)-6-cyanopyridine-4-boronic acid 2-(Ethyl-d5)-6-cyanopyridine-4-boronic acid 2225176-25-8 C8H9BN2O2
2-(Iodopyridine-d3)-4-boronic acid 2-(Iodopyridine-d3)-4-boronic acid 2225179-25-7 C5H5BINO2
2-(iso-Butyl-d9)-pyridine-5-boronic acid 2-(iso-Butyl-d9)-pyridine-5-boronic acid 2225178-17-4 C9H14BNO2
2-(iso-Propyl-d7)-6-trifluoromethylpyridine-4-boronic acid 2-(iso-Propyl-d7)-6-trifluoromethylpyridine-4-boronic acid 2225175-73-3 C9H11BF3NO2
2-(n-Propoxy-d7)-pyridine-4-boronic acid 2-(n-Propoxy-d7)-pyridine-4-boronic acid 2225172-85-8 C8H12BNO3
2-(sec-Butyl-d9)-pyridine-5-boronic acid 2-(sec-Butyl-d9)-pyridine-5-boronic acid 2225152-77-0 C9H14BNO2
2,4-Dibromopyridine-3,5,6-d3 2,4-Dibromopyridine-3,5,6-d3 1643579-90-1 C5Br2D3N
2,4-Dichloro-6-(n-propyl-d7)-pyrimidine 2,4-Dichloro-6-(n-propyl-d7)-pyrimidine 1185316-42-0 C7H8Cl2N2
2-Amino-4-(iso-propyl-d7)-pyridine 2-Amino-4-(iso-propyl-d7)-pyridine 1185316-00-0 C8H12N2
2-Amino-4-(methyl-d3)-pyridine 2-Amino-4-(methyl-d3)-pyridine 475502-23-9 C6H5D3N2
2-Amino-4-(tert-butyl-d9)-pyridine 2-Amino-4-(tert-butyl-d9)-pyridine 1643576-24-2 C9H14N2
2-Amino-4-[(tert-butyl)pyridine-d12] 2-Amino-4-[(tert-butyl)pyridine-d12] 1643541-79-0 C9H14N2
2-Amino-5-(iso-propyl)pyridine-d10 2-Amino-5-(iso-propyl)pyridine-d10 1643562-84-8 C8H12N2
2-Amino-5-(methoxy-d3)-pyridine 2-Amino-5-(methoxy-d3)-pyridine 1643575-32-9 C6H8N2O
2-Amino-5-(pyrrolidino-d8)-pyridine 2-Amino-5-(pyrrolidino-d8)-pyridine 1643562-86-0 C9H5D8N3
2-Amino-6-(methyl-13C, d3)pyridine 2-Amino-6-(methyl-13C, d3)pyridine 1227960-36-2 C6H5D3N2
2-Bromo-4-(diethylamino)pyridine-d13 2-Bromo-4-(diethylamino)pyridine-d13 1643579-78-5 C9H13BrN2
2-Bromo-4-(ethyl-d5)-pyridine 2-Bromo-4-(ethyl-d5)-pyridine 1185313-78-3 C7H8BrN
2-Bromo-4-(morpholino-d8)-pyridine 2-Bromo-4-(morpholino-d8)-pyridine 1643563-38-5 C9H11BrN2O
2-Bromo-4-ethoxycarbonylpyridine-d8 2-Bromo-4-ethoxycarbonylpyridine-d8 1643563-17-0 C8H8BrNO2
2-Bromo-4-methoxycarbonylpyridine-d6 2-Bromo-4-methoxycarbonylpyridine-d6 1643539-52-9 C7H6BrNO2
2-Bromo-5-(diethylamino-d10)-pyridine 2-Bromo-5-(diethylamino-d10)-pyridine 1643538-89-9 C9H13BrN2
2-Bromo-5-(ethoxy-d5)-pyridine 2-Bromo-5-(ethoxy-d5)-pyridine 1643541-71-2 C7H8BrNO
2-Bromo-5-(iso-propoxy-d7)-pyridine 2-Bromo-5-(iso-propoxy-d7)-pyridine 1643542-00-0 C8H3BrD7NO
2-Bromo-5-cyanopyridine-d3 2-Bromo-5-cyanopyridine-d3 1643576-36-6 C6H3BrN2
2-Bromo-6-(acetyl-d3)-pyridine 2-Bromo-6-(acetyl-d3)-pyridine 1185320-20-0 C7H3BrD3NO
2-Bromo-6-(methylamino-d3)-pyridine 2-Bromo-6-(methylamino-d3)-pyridine 1185310-42-2 C6H7BrN2
2-Bromo-6-(n-propyl)pyridine-d10 2-Bromo-6-(n-propyl)pyridine-d10 1643564-20-8 C8H10BrN
2-Bromo-6-(trifluoromethyl)pyridine-d3 2-Bromo-6-(trifluoromethyl)pyridine-d3 1643575-62-5 C6BrD3F3N
2-Bromo-6-{N-Boc-[(piperazin-1-yl)pyridine-d11]} 2-Bromo-6-{N-Boc-[(piperazin-1-yl)pyridine-d11]} 1643577-01-8 C14H20BrN3O2
2-Chloro-6-(n-propyl-d7)-4-aminopyridine 2-Chloro-6-(n-propyl-d7)-4-aminopyridine 1185315-63-2 C8H4ClD7N2
2-Fluoro-4-bromopyridine-d3 2-Fluoro-4-bromopyridine-d3 1643539-50-7 C5H3BrFN
2-Iodopyridine-d4 2-Iodopyridine-d4 1643564-74-2 C5H4IN
3-Amino-5-(ethyl-d5)-pyridine 3-Amino-5-(ethyl-d5)-pyridine 1643542-37-3 C7H10N2
3-Amino-5-(n-propyl-d7)-pyridine 3-Amino-5-(n-propyl-d7)-pyridine 1643537-59-0 C8H12N2
3-Amino-6-(methyl-d3)-pyridazine 3-Amino-6-(methyl-d3)-pyridazine 1185309-73-2 C5H4D3N3
3-Amino-6-(n-propyl-d7)-pyridazine 3-Amino-6-(n-propyl-d7)-pyridazine 1185307-17-8 C7H11N3
3-Bromo-(4-methyl-5-ethyl-d8)-pyridine 3-Bromo-(4-methyl-5-ethyl-d8)-pyridine 1643562-68-8 C8H10BrN
3-Bromo-[5-methyl-6-(n-propyl)-d10]-pyridine 3-Bromo-[5-methyl-6-(n-propyl)-d10]-pyridine 1643541-81-4 C9H12BrN
3-Bromo-[6-methyl-5-(iso-propyl)-d10]-pyridine 3-Bromo-[6-methyl-5-(iso-propyl)-d10]-pyridine 1643537-80-7 C9H12BrN
3-Bromo-5-(iso-propyl-d7)-pyridine 3-Bromo-5-(iso-propyl-d7)-pyridine 1185313-10-3 C8H10BrN
3-Bromo-5-(methylethylamino)pyridine-d11 3-Bromo-5-(methylethylamino)pyridine-d11 1643577-07-4 C8H11BrN2
3-Bromo-5-(pyrrolidino-d8)-pyridine 3-Bromo-5-(pyrrolidino-d8)-pyridine 1643537-66-9 C9H11BrN2
3-Bromo-5-(tert-butyl)pyridine-d12 3-Bromo-5-(tert-butyl)pyridine-d12 1643537-60-3 C9BrD12N
3-Bromo-5-methylpyridine-d6 3-Bromo-5-methylpyridine-d6 1643564-84-4 C6H6BrN
3-Bromo-6-(diethylamino-d10)-pyridine 3-Bromo-6-(diethylamino-d10)-pyridine 1643562-96-2 C9H13BrN2
3-Bromo-6-(iso-propoxy-d7)-pyridazine 3-Bromo-6-(iso-propoxy-d7)-pyridazine 1185317-62-7 C7H9BrN2O
3-Bromo-6-(iso-propyl-d7)-pyridine 3-Bromo-6-(iso-propyl-d7)-pyridine 1643577-13-2 C8H10BrN
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