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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-Chloro-5-bromo-2-(3-fluorophenyl)pyrimidine 4-Chloro-5-bromo-2-(3-fluorophenyl)pyrimidine 1399480-96-6 C10H5BrClFN2
4-Chloro-5-bromo-2-(4-tolyl)pyrimidine 4-Chloro-5-bromo-2-(4-tolyl)pyrimidine 1399481-13-0 C11H8BrClN2
4-Chloro-5-bromo-2-(cyclohexyloxy)pyrimidine 4-Chloro-5-bromo-2-(cyclohexyloxy)pyrimidine 1399482-56-4 C10H12BrClN2O
4-Chloro-5-bromo-2-phenylpyrimidine 4-Chloro-5-bromo-2-phenylpyrimidine 26740-70-5 C10H6BrClN2
4-chloro-6-(1,4-dioxan-2-yl)pyrimidine 4-chloro-6-(1,4-dioxan-2-yl)pyrimidine 2222935-23-9 C8H9ClN2O2
4-Chloro-6-bromo-2-(tert-butoxy)pyrimidine 4-Chloro-6-bromo-2-(tert-butoxy)pyrimidine 1563532-29-5 C8H10BrClN2O
4-fluoro-2-(methoxy-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,6-d2 4-fluoro-2-(methoxy-d3)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,6-d2 2256705-23-2 C12H17BFNO3
4-Hydroxy-2-(4-tolyl)pyridine 4-Hydroxy-2-(4-tolyl)pyridine 1159814-51-3 C12H11NO
4-Hydroxy-2-(cyclopentyl)pyridine 4-Hydroxy-2-(cyclopentyl)pyridine 1314353-82-6 C10H13NO
4-Hydroxy-2-phenyl-6-(2-methyl-5-thiazolyl)pyrimidine 4-Hydroxy-2-phenyl-6-(2-methyl-5-thiazolyl)pyrimidine 1159814-75-1 C14H11N3OS
4-Hydroxy-2-phenyl-6-(5-pyrimidyl)pyrimidine 4-Hydroxy-2-phenyl-6-(5-pyrimidyl)pyrimidine 1159814-56-8 C14H10N4O
4-Hydroxy-6-(4-thiazolyl)-2-cyclopropylpyrimidine 4-Hydroxy-6-(4-thiazolyl)-2-cyclopropylpyrimidine 1159815-06-1 C10H9N3OS
4-Hydroxy-6-(piperazin-1-yl)pyrimidine 4-Hydroxy-6-(piperazin-1-yl)pyrimidine 1159568-13-4 C8H12N4O
4-methyl-2-(prop-1-en-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 4-methyl-2-(prop-1-en-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2256758-22-0 C13H20BNO2S
5-(1H-imidazol-1-yl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 5-(1H-imidazol-1-yl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2256709-66-5 C14H18BN3O2
5-(2-bromophenyl)pyrimidine-2,4,6-d3 5-(2-bromophenyl)pyrimidine-2,4,6-d3 2256711-24-5 C10H7BrN2
5-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 5-(4-(methyl-d3)-1H-pyrazol-1-yl-3,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2256706-47-3 C15H20BN3O2
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(thiazol-5-yl)pyridin-2(1H)-one 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(thiazol-5-yl)pyridin-2(1H)-one 2256754-92-2 C14H17BN2O3S
5-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(4-bromo-1H-pyrazol-1-yl-3,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256706-57-5 C14H15BBrD2N3O2
5-(tetrahydro-2H-pyran-2-yl)pyrimidin-2-amine 5-(tetrahydro-2H-pyran-2-yl)pyrimidin-2-amine 1622834-61-0 C9H13N3O
5-Amino-2-(1H-pyrrol-1-yl)thiazole 5-Amino-2-(1H-pyrrol-1-yl)thiazole 1314356-50-7 C7H7N3S
5-Amino-2-(3-fluorophenyl)thiazole 5-Amino-2-(3-fluorophenyl)thiazole 1159818-22-0 C9H7FN2S
5-Amino-2-(3-trifluoromethylphenyl)thiazole 5-Amino-2-(3-trifluoromethylphenyl)thiazole 1159814-64-8 C10H7F3N2S
5-Amino-2-(cyclohexenyl)thiazole 5-Amino-2-(cyclohexenyl)thiazole 1159816-05-3 C9H12N2S
5-bromo-2-(2-bromophenyl)pyridine-3,4,6-d3 5-bromo-2-(2-bromophenyl)pyridine-3,4,6-d3 2256711-52-9 C11H4Br2D3N
5-BROMO-2-(2-FLUOROPHENYL)PYRIDIN-4-AMINE 5-BROMO-2-(2-FLUOROPHENYL)PYRIDIN-4-AMINE 1381943-62-9 C11H8BrFN2
5-bromo-2-(3-bromophenyl)pyridine-3,4,6-d3 5-bromo-2-(3-bromophenyl)pyridine-3,4,6-d3 2256711-88-1 C11H7Br2N
5-Bromo-2-(3-furyl)thiazole 5-Bromo-2-(3-furyl)thiazole 1142194-99-7 C7H4BrNOS
5-BROMO-2-(4-HYDROXYPIPERIDIN-1-YL)PYRIDIN-4-AMINE 5-BROMO-2-(4-HYDROXYPIPERIDIN-1-YL)PYRIDIN-4-AMINE 1381937-97-8 C10H14BrN3O
5-BROMO-2-(4-METHYLPHENYL)PYRIDIN-4-AMINE 5-BROMO-2-(4-METHYLPHENYL)PYRIDIN-4-AMINE 1381935-48-3 C12H11BrN2
5-bromo-2-iodopyrimidine-4,6-d2 5-bromo-2-iodopyrimidine-4,6-d2 2259315-62-1 C4H2BrIN2
5-Bromo-4-(iso-propyl)-2-(dimethylamino)thiazole 5-Bromo-4-(iso-propyl)-2-(dimethylamino)thiazole 1643539-06-3 C8H13BrN2S
5-Bromo-4-(n-propyl)-2-(pyrrolidino)thiazole 5-Bromo-4-(n-propyl)-2-(pyrrolidino)thiazole 1643543-35-4 C10H15BrN2S
5-Bromo-4-cyclopropyl-2-cyanothiazole 5-Bromo-4-cyclopropyl-2-cyanothiazole 1314357-24-8 C7H5BrN2S
5-Bromo-4-hydroxy-2-(cyclopentyl)pyrimidine 5-Bromo-4-hydroxy-2-(cyclopentyl)pyrimidine 1500229-44-6 C9H11BrN2O
5-Bromo-4-methyl-2-(diethylamino)thiazole 5-Bromo-4-methyl-2-(diethylamino)thiazole 1538537-73-3 C8H13BrN2S
5-Hydroxy-2-(4-Fluorophenyl)thiazole 5-Hydroxy-2-(4-Fluorophenyl)thiazole 1159814-47-7 C9H6FNOS
5-PROPOXYPYRIDIN-3-YLAMINE 5-PROPOXYPYRIDIN-3-YLAMINE 1563533-46-9 C8H12N2O
6-(2-METHYLPROPYL)PYRIDIN-3-AMINE 6-(2-METHYLPROPYL)PYRIDIN-3-AMINE 1241675-03-5 C9H14N2
6-(3-CHLOROPHENYL)PYRIDIN-2-AMINE 6-(3-CHLOROPHENYL)PYRIDIN-2-AMINE 882014-33-7 C11H9ClN2
6-(methoxy-d3)pyridin-2-amine 6-(methoxy-d3)pyridin-2-amine 2259316-11-3 C6H8N2O
6-(tetrahydro-2H-pyran-3-yl)pyridin-2-ol 6-(tetrahydro-2H-pyran-3-yl)pyridin-2-ol 2222934-55-4 C10H13NO2
6-(tetrahydrofuran-3-yl)pyridin-2-ol 6-(tetrahydrofuran-3-yl)pyridin-2-ol 2222934-44-1 C9H11NO2
6-ISOPROPYL-6'-TERT-BUTYL-2,2'-BIPYRIDINE 6-ISOPROPYL-6'-TERT-BUTYL-2,2'-BIPYRIDINE 1434127-21-5 C17H22N2
N-(ethyl-d5)-N-(methyl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-amine-3,5,6-d3 N-(ethyl-d5)-N-(methyl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-amine-3,5,6-d3 2241874-77-9 C14H23BN2O2
pyrimidin-d3-2-ol pyrimidin-d3-2-ol 128474-97-5 C4H4N2O
tert-butyl 2-(3-aminophenyl)morpholine-4-carboxylate tert-butyl 2-(3-aminophenyl)morpholine-4-carboxylate 1312566-26-9 C15H22N2O3
tert-butyl 2-(4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazol-2-yl)pyrrolidine-1-carboxylate tert-butyl 2-(4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazol-2-yl)pyrrolidine-1-carboxylate 2256758-23-1 C19H31BN2O4S
tert-butyl 3-(5-bromopyridin-2-yl)piperidine-1-carboxylate tert-butyl 3-(5-bromopyridin-2-yl)piperidine-1-carboxylate 1245915-18-7 C15H21BrN2O2
tert-butyl 4-(2-bromopyrimidin-5-yl)piperidine-1-carboxylate tert-butyl 4-(2-bromopyrimidin-5-yl)piperidine-1-carboxylate 2222935-37-5 C14H20BrN3O2
tert-butyl 4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl-3,4,5-d3)piperazine-1-carboxylate-2,2,3,3,5,5,6,6-d8 tert-butyl 4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl-3,4,5-d3)piperazine-1-carboxylate-2,2,3,3,5,5,6,6-d8 2241870-10-8 C20H32BN3O4
(R)-3-Fluoropyrrolidine-1-sulfonyl chloride (R)-3-Fluoropyrrolidine-1-sulfonyl chloride 1411774-27-0 C4H7ClFNO2S
(S)-Ethyl 6-(5-bromofuran-2-yl)-7,9-dimethyl-8,10-dioxo-11-phenyl-7,8,9,10-tetrahydro-6H-benzo[b]pyrimido[4',5':3,4]pyrrolo[1,2-d][1,4]oxazine-2-carboxylate (S)-Ethyl 6-(5-bromofuran-2-yl)-7,9-dimethyl-8,10-dioxo-11-phenyl-7,8,9,10-tetrahydro-6H-benzo[b]pyrimido[4',5':3,4]pyrrolo[1,2-d][1,4]oxazine-2-carboxylate 1415390-49-6 C28H22BrN3O6
2-methyl-1H-pyrrolo[2,3-b]pyridin-4-amine 2-methyl-1H-pyrrolo[2,3-b]pyridin-4-amine 1638771-68-2 C8H9N3
(3S,4R)-3-amino-4-hydroxypyrrolidin-2-one hydrochloride (3S,4R)-3-amino-4-hydroxypyrrolidin-2-one hydrochloride 2446872-13-3 C4H9ClN2O2
(2-(tert-butoxy)pyrimidin-5-yl)boronic acid (2-(tert-butoxy)pyrimidin-5-yl)boronic acid 2225180-17-4 C8H13BN2O3
5-Bromo-2-(oxetan-3-yloxy)-pyridine 5-Bromo-2-(oxetan-3-yloxy)-pyridine 1600912-06-8 C8H8BrNO2
1-(2-bromopyridin-4-yl)piperazine 1-(2-bromopyridin-4-yl)piperazine 854159-48-1 C9H12BrN3
(5S)-2 2 3-TRIMETHYL-5-PHENYLMETHYL-4-I& (5S)-2 2 3-TRIMETHYL-5-PHENYLMETHYL-4-I& 278173-23-2 C13H18N2O.ClH
3-TERT-BUTYLISOXAZOL-5-AMINE 3-TERT-BUTYLISOXAZOL-5-AMINE 59669-59-9 C7H12N2O
2-[3-(TRIFLUOROMETHYL)PHENYL]-1,3-THIAZOLE- 2-[3-(TRIFLUOROMETHYL)PHENYL]-1,3-THIAZOLE- 192063-44-8 C10H6F3NS
(S)-BAY 73-6691 (S)-BAY 73-6691 794568-91-5 C15H12ClF3N4O
6-methoxy-5-(tetrahydrofuran-2-yl)pyridin-3-amine 6-methoxy-5-(tetrahydrofuran-2-yl)pyridin-3-amine 2294947-94-5 C10H14N2O2
2-Bromo-5-(tetrahydrofuran-2-yl)pyridine 2-Bromo-5-(tetrahydrofuran-2-yl)pyridine 1353854-56-4 C9H10BrNO
2-Brom-6-(tetrahydrofuran-2-yl)pyridine 2-Brom-6-(tetrahydrofuran-2-yl)pyridine 1353853-93-6 C9H10BrNO
6-(Oxan-2-yl)pyridine-3-boronic acid pinacol ester 6-(Oxan-2-yl)pyridine-3-boronic acid pinacol ester 2223005-94-3 C16H24BNO3
2,6-bis[1,1-bis(pyridin-2-yl)ethyl]pyridine 2,6-bis[1,1-bis(pyridin-2-yl)ethyl]pyridine 105631-67-2 C29H25N5
3-chloroimidazo[1,2-a]pyridine-6-sulfonyl chloride 3-chloroimidazo[1,2-a]pyridine-6-sulfonyl chloride 2306270-26-6 C7H4Cl2N2O2S
Dodecanedioic acid, 1,12-bis(2,5-dioxo-1-pyrrolidinyl) ester Dodecanedioic acid, 1,12-bis(2,5-dioxo-1-pyrrolidinyl) ester 75472-90-1 C20H28N2O8
1H-Isoindole-1,3(2H)-dione,5,5'-oxybis[2-methyl- 1H-Isoindole-1,3(2H)-dione,5,5'-oxybis[2-methyl- 27507-54-6 C18H12N2O5
Benzoicacid,3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)- Benzoicacid,3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)- 223646-24-0 C12H13NO5S
1,4-Di(pyridin-2-yl)benzene 1,4-Di(pyridin-2-yl)benzene 57477-09-5 C16H12N2
7-chloronaphtho[1,2-b]benzofuran 7-chloronaphtho[1,2-b]benzofuran 2411141-56-3 C16H9ClO
3-methoxy-1-methyl-1H-Pyrazole-4-carboxaldehyde 3-methoxy-1-methyl-1H-Pyrazole-4-carboxaldehyde 875570-95-9 C6H8N2O2
1-(2-Bromo-3-pyridinyl)piperazine 1-(2-Bromo-3-pyridinyl)piperazine 854159-47-0 C9H12BrN3
7-Chloro-5-(chloromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine 7-Chloro-5-(chloromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine 63882-72-4 C6H4Cl2N4
5-((Benzyloxy)carbonyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid 5-((Benzyloxy)carbonyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid 100307-49-1 C15H15N3O4
2-(Chloromethyl)thieno[3,2-d]pyrimidine 2-(Chloromethyl)thieno[3,2-d]pyrimidine 77294-17-8 C7H5ClN2S
5-Bromo-[1,2,4]triazolo[1,5-a]pyrimidine 5-Bromo-[1,2,4]triazolo[1,5-a]pyrimidine 154695-81-5 C5H3BrN4
6-Methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde 6-Methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde 1263059-02-4 C8H7N3O
(R)-(5-oxopyrrolidin-2-yl)methyl methanesulfonate (R)-(5-oxopyrrolidin-2-yl)methyl methanesulfonate 128811-47-2 C6H11NO4S
(S)-3-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol (S)-3-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol 1163680-85-0 C6H7N3O4
6,6-Dimethyl-6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione 6,6-Dimethyl-6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione 67566-51-2 C9H12N2O2
1,3-Diphenyl-3-imidazo[4,5-b]pyrazinium Iodide 1,3-Diphenyl-3-imidazo[4,5-b]pyrazinium Iodide 1311465-22-1 C17H13IN4
2,3-DIHYDRO-2-METHYLBENZOFURAN 2,3-DIHYDRO-2-METHYLBENZOFURAN 1746-11-8 C9H10O
4-CHLORO-2-METHOXY-PYRIDINE 4-CHLORO-2-METHOXY-PYRIDINE 72141-44-7 C6H6ClNO
3,5-DIBROMO-2-METHYLTHIOPHENE 3,5-DIBROMO-2-METHYLTHIOPHENE 29421-73-6 C5H4Br2S
7-METHYL-2-PHENYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID 7-METHYL-2-PHENYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID 220465-49-6 C15H12N2O2
2-NITROFURAN 2-NITROFURAN 609-39-2 C4H3NO3
N-Boc-2-piperidone N-Boc-2-piperidone 85908-96-9 C10H17NO3
1-(4-Methoxyphenyl)piperazine dihydrochloride 1-(4-Methoxyphenyl)piperazine dihydrochloride 38869-47-5 C11H18Cl2N2O
5-CHLORO-2-BENZOTHIAZOLINONE 5-CHLORO-2-BENZOTHIAZOLINONE 20600-44-6 C7H4ClNOS
2-CHLORO-4-HYDROXYQUINAZOLINE 2-CHLORO-4-HYDROXYQUINAZOLINE 607-69-2 C8H5ClN2O
4-NITRO-1H-IMIDAZOLE-5-CARBOXYLIC ACID 4-NITRO-1H-IMIDAZOLE-5-CARBOXYLIC ACID 40507-59-3 C4H3N3O4
Tetrahydrofuran-3-yl)methanamine Tetrahydrofuran-3-yl)methanamine 165253-31-6 C5H11NO
(R,R)-2,2'-(DIMETHYLMETHYLENE)BIS(4-PHENYL-2-OXAZOLINE) (R,R)-2,2'-(DIMETHYLMETHYLENE)BIS(4-PHENYL-2-OXAZOLINE) 150529-93-4 C21H22N2O2
4-MORPHOLINECARBONITRILE 4-MORPHOLINECARBONITRILE 1530-89-8 C5H8N2O
2,3-Dihydro-2,2-dimethyl-7-benzofuranol 2,3-Dihydro-2,2-dimethyl-7-benzofuranol 1563-38-8 C10H12O2
Piperonyl aldehyde Piperonyl aldehyde 120-57-0 C8H6O3
Pseudothiohydantoin Pseudothiohydantoin 556-90-1 C3H4N2OS
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