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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-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 4-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,5,6-d3 2241874-67-7 C11H15BClNO2
4-Chloro-2-(tetrahydrofuran-3-yl)pyridine 4-Chloro-2-(tetrahydrofuran-3-yl)pyridine 1434127-61-3 C9H10ClNO
4-Chloro-2-phenyl-6-(2-methyl-4-thiazolyl)pyrimidine 4-Chloro-2-phenyl-6-(2-methyl-4-thiazolyl)pyrimidine 1159821-82-5 C14H10ClN3S
4-Chloro-3-(n-propoxy)pyridine 4-Chloro-3-(n-propoxy)pyridine 1563529-09-8 C8H10ClNO
4-Chloro-5-bromo-2-(1H-pyrazol-1-yl)pyrimidine 4-Chloro-5-bromo-2-(1H-pyrazol-1-yl)pyrimidine 1399482-64-4 C7H4BrClN4
4-Chloro-5-bromo-2-(3-methyl-1H-pyrazol-1-yl)pyrimidine 4-Chloro-5-bromo-2-(3-methyl-1H-pyrazol-1-yl)pyrimidine 1399481-54-9 C8H6BrClN4
4-Chloro-5-bromo-2-(4-chlorophenyl)pyrimidine 4-Chloro-5-bromo-2-(4-chlorophenyl)pyrimidine 1399482-28-0 C10H5BrCl2N2
4-Chloro-5-bromo-2-(iso-propoxy)pyrimidine 4-Chloro-5-bromo-2-(iso-propoxy)pyrimidine 1399481-53-8 C7H8BrClN2O
4-Chloro-6-(2-methyl-4-thiazolyl)-2-cyclopropylpyrimidine 4-Chloro-6-(2-methyl-4-thiazolyl)-2-cyclopropylpyrimidine 1159815-11-8 C11H10ClN3S
4-Chloro-6-(4-pyridyl)-2-cyclopropylpyrimidine 4-Chloro-6-(4-pyridyl)-2-cyclopropylpyrimidine 1159820-39-9 C12H10ClN3
4-Chloro-6-methyl-2-(3-furyl)pyrimidine 4-Chloro-6-methyl-2-(3-furyl)pyrimidine 1159815-88-9 C9H7ClN2O
4-chloropyridine-2,3,5,6-d4 hydrochloride 4-chloropyridine-2,3,5,6-d4 hydrochloride 1279827-37-0 C5H5Cl2N
4-fluoro-2-(tetrahydrofuran-2-yl)pyridine 4-fluoro-2-(tetrahydrofuran-2-yl)pyridine 2256709-29-0 C9H10FNO
4-Hydroxy-2-(2-thienyl)thiazole 4-Hydroxy-2-(2-thienyl)thiazole 285995-74-6 C7H5NOS2
4-Hydroxy-2-(3,4-difluorophenyl)thiazole 4-Hydroxy-2-(3,4-difluorophenyl)thiazole 1159814-83-1 C9H5F2NOS
4-Hydroxy-2-cyclobutylthiazole 4-Hydroxy-2-cyclobutylthiazole 1159817-26-1 C7H9NOS
4-Hydroxy-2-phenyl-6-(4-pyridyl)pyrimidine 4-Hydroxy-2-phenyl-6-(4-pyridyl)pyrimidine 263243-59-0 C15H11N3O
4-Hydroxy-3-phenylpyridine 4-Hydroxy-3-phenylpyridine 19069-62-6 C11H9NO
4-methyl-2-(tetrahydrofuran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 4-methyl-2-(tetrahydrofuran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2256758-26-4 C14H22BNO3S
5-(1H-pyrazol-1-yl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 5-(1H-pyrazol-1-yl-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2256709-93-8 C14H15BD3N3O2
5-(3-(methyl-d3)-1H-pyrazol-1-yl-4,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 5-(3-(methyl-d3)-1H-pyrazol-1-yl-4,5-d2)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2256705-37-8 C15H20BN3O2
5-(4-bromophenyl)-2-(methyl-d3)pyridine-3,4,6-d3 5-(4-bromophenyl)-2-(methyl-d3)pyridine-3,4,6-d3 2256711-94-9 C12H10BrN
5-(4-BROMOPHENYL)PYRIDIN-2-AMINE 5-(4-BROMOPHENYL)PYRIDIN-2-AMINE 1191616-44-0 C11H9BrN2
5-(4-tetrahydropyranyl)-3-acetoxypyridine 5-(4-tetrahydropyranyl)-3-acetoxypyridine 1434127-69-1 C12H15NO3
5-(methoxy-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 5-(methoxy-d3)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3,4,6-d3 2241867-70-7 C12H18BNO3
5-(methyl-13C-d3)pyridin-3-amine 5-(methyl-13C-d3)pyridin-3-amine 1643543-00-3 C6H5D3N2
5-(tetrahydrofuran-2-yl)pyridin-3-amine 5-(tetrahydrofuran-2-yl)pyridin-3-amine 1888880-19-0 C9H12N2O
5-(tetrahydrofuran-3-yl)pyridin-3-amine 5-(tetrahydrofuran-3-yl)pyridin-3-amine 1892538-43-0 C9H12N2O
5-Amino-2-(2-methoxyphenyl)thiazole 5-Amino-2-(2-methoxyphenyl)thiazole 1159819-67-6 C10H10N2OS
5-Amino-2-(4-ethylphenyl)thiazole 5-Amino-2-(4-ethylphenyl)thiazole 1159814-59-1 C11H12N2S
5-Amino-2-(piperidin-3-yl)pyrimidine 5-Amino-2-(piperidin-3-yl)pyrimidine 1622835-84-0 C9H14N4
5-BROMO-1-(4-TETRAHYDROPYRANYL)-1H-PYRAZOLE 5-BROMO-1-(4-TETRAHYDROPYRANYL)-1H-PYRAZOLE 1369237-49-9 C8H11BrN2O
5-BROMO-2-(2-HYDROXYPIPERIDIN-1-YL)PYRIDIN-4-AMINE 5-BROMO-2-(2-HYDROXYPIPERIDIN-1-YL)PYRIDIN-4-AMINE 1381938-20-0 C10H14BrN3O
5-BROMO-2-(3-FLUOROPHENYL)PYRIDIN-4-AMINE 5-BROMO-2-(3-FLUOROPHENYL)PYRIDIN-4-AMINE 1381941-00-9 C11H8BrFN2
5-BROMO-2-(3-METHYLPHENYL)PYRIDIN-4-AMINE 5-BROMO-2-(3-METHYLPHENYL)PYRIDIN-4-AMINE 1381943-82-3 C12H11BrN2
5-BROMO-2-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDIN-4-AMINE 5-BROMO-2-(4-METHYL-1H-PYRAZOL-1-YL)PYRIDIN-4-AMINE 1381933-24-9 C9H9BrN4
5-Bromo-2-(4-tert-butylphenyl)thiazole 5-Bromo-2-(4-tert-butylphenyl)thiazole 1159822-05-5 C13H14BrNS
5-bromo-2-(methoxy-d3)pyrimidine-4,6-d2 5-bromo-2-(methoxy-d3)pyrimidine-4,6-d2 2256707-51-2 C5H5BrN2O
5-Bromo-2-(N-Boc-piperidin-3-yl)pyrimidine 5-Bromo-2-(N-Boc-piperidin-3-yl)pyrimidine 1563532-49-9 C14H20BrN3O2
5-BROMO-2-(THIOPHEN-3-YL)PYRIDIN-4-AMINE 5-BROMO-2-(THIOPHEN-3-YL)PYRIDIN-4-AMINE 1381943-73-2 C9H7BrN2S
5-BROMO-2-PHENYLPYRIDIN-4-AMINE 5-BROMO-2-PHENYLPYRIDIN-4-AMINE 1381934-75-3 C11H9BrN2
5-Bromo-4-(iso-propyl)-2-(n-propyl)thiazole 5-Bromo-4-(iso-propyl)-2-(n-propyl)thiazole 1643543-09-2 C9H14BrNS
5-Bromo-4-(n-propyl)-2-methoxythiazole 5-Bromo-4-(n-propyl)-2-methoxythiazole 1643562-93-9 C7H10BrNOS
5-Bromo-4-ethyl-2-(diethylamino)thiazole 5-Bromo-4-ethyl-2-(diethylamino)thiazole 1643543-31-0 C9H15BrN2S
5-Bromo-4-methyl-2-(morpholino)thiazole 5-Bromo-4-methyl-2-(morpholino)thiazole 1531837-03-2 C8H11BrN2OS
5-Hydroxy-5'-chloro-2,2'-bipyridine 5-Hydroxy-5'-chloro-2,2'-bipyridine 1185313-74-9 C10H7ClN2O
6-(2-BROMOPHENYL)PYRIDIN-2-AMINE 6-(2-BROMOPHENYL)PYRIDIN-2-AMINE 1292186-54-9 C11H9BrN2
6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bipyridine-3,3',4,4',5,5',6'-d7 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bipyridine-3,3',4,4',5,5',6'-d7 2241866-69-1 C16H19BN2O2
6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one-3,4,5-d3 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one-3,4,5-d3 2241870-02-8 C11H16BNO3
6-(ethoxy-d5)pyridin-2-amine 6-(ethoxy-d5)pyridin-2-amine 2259316-16-8 C7H5D5N2O
6-(OXOLAN-3-YLOXY)-3-PYRIDAZINAMINE 6-(OXOLAN-3-YLOXY)-3-PYRIDAZINAMINE 1599480-40-6 C8H11N3O2
6-(tetrahydrofuran-2-yl)pyridazin-3-ol 6-(tetrahydrofuran-2-yl)pyridazin-3-ol 1896594-34-5 C8H10N2O2
6-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 6-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 2256754-90-0 C14H21BN2O2
N,N-bis(boc)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-amine-3,4,5-d3 N,N-bis(boc)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-amine-3,4,5-d3 2241870-00-6 C21H30BD3N2O6
2,4-dichloro-6-(3,4-difluorophenyl)-1,3,5-triazine 2,4-dichloro-6-(3,4-difluorophenyl)-1,3,5-triazine 1227959-18-3 C9H3Cl2F2N3
2-Bromo-1,3-oxazole hydrochloride 2-Bromo-1,3-oxazole hydrochloride 1305712-69-9 C3H3BrClNO
5-Bromo-8-methylquinoxaline 5-Bromo-8-methylquinoxaline 1360599-43-4 C9H7BrN2
tert-Butyl 4-(4-hydroxypyridin-2-yl)piperazine-1-carboxylate tert-Butyl 4-(4-hydroxypyridin-2-yl)piperazine-1-carboxylate 1453265-70-7 C14H21N3O3
4-(Octadecyloxy)-1,3-benzenediamine 4-(Octadecyloxy)-1,3-benzenediamine 155096-60-9 C24H44N2O
Tris([2,2'-bipyridine]-4,4'-diamine)ruthenium(II)dichloride Tris([2,2'-bipyridine]-4,4'-diamine)ruthenium(II)dichloride C30H30Cl2N12Ru
5-bromo-2-(trifluoromethyl)pyridin-4-amine 5-bromo-2-(trifluoromethyl)pyridin-4-amine 1369921-11-8 C6H4BrF3N2
Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-4,5-dimethyl-2H-imidazol-2-ylidene}gold(I) Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-4,5-dimethyl-2H-imidazol-2-ylidene}gold(I) 1192141-66-4 C29H41AuClN2-
2'-chloro-2,3'-bipyridine 2'-chloro-2,3'-bipyridine 93297-77-9 C10H7ClN2
Pyrimidine, 4,6-dichloro-2-[(1E)-2-phenylethenyl]- Pyrimidine, 4,6-dichloro-2-[(1E)-2-phenylethenyl]- 934353-78-3 C12H8Cl2N2
pyrimidin-2,4-d2-5-ol pyrimidin-2,4-d2-5-ol 2222933-94-8 C4H4N2O
tert-butyl 2-(3-bromophenyl)morpholine-4-carboxylate tert-butyl 2-(3-bromophenyl)morpholine-4-carboxylate 1622835-96-4 C15H20BrNO3
tert-butyl 3-(6-(tert-butoxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperidine-1-carboxylate tert-butyl 3-(6-(tert-butoxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperidine-1-carboxylate 2256754-74-0 C25H41BN2O5
tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate-2,2,3,3,5,6,6-d7 tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate-2,2,3,3,5,6,6-d7 2241870-23-3 C16H21BD7NO4
tert-butyl 4-(5-aminopyridin-3-yl)piperidine-1-carboxylate tert-butyl 4-(5-aminopyridin-3-yl)piperidine-1-carboxylate 762298-12-4 C15H23N3O2
5-chloro-3H-imidazo[4,5-b]pyridine-2-thiol 5-chloro-3H-imidazo[4,5-b]pyridine-2-thiol 40851-97-6 C6H4ClN3S
BIS(2-FURYL)CHLOROPHOSPHINE BIS(2-FURYL)CHLOROPHOSPHINE 181257-35-2 C8H6ClO2P
6-isopropylquinazoline 6-isopropylquinazoline 1059158-62-1 C11H12N2
2-(1H-IMIDAZOL-1-YL)ETHANAMINE HYDROCHLORIDE 2-(1H-IMIDAZOL-1-YL)ETHANAMINE HYDROCHLORIDE 154094-97-0 C5H10ClN3
(2S,4S)-1-(tert-Butoxycarbonyl)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidine-2-carboxylic acid (2S,4S)-1-(tert-Butoxycarbonyl)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidine-2-carboxylic acid 1821705-03-6 C24H33N5O4
(2S,5S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-5-phenylpyrrolidine-2-carboxylic acid (2S,5S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-5-phenylpyrrolidine-2-carboxylic acid 1219953-60-2 C26H23NO4
1-(sec-butyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 1-(sec-butyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 2222997-43-3 C13H23BN2O2
tert-butyl 4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate tert-butyl 4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1(2H)-carboxylate 3124612-49-0 C17H30BNO4
3-Bromo-6-cyclopropyl-2-methylpyridine 3-Bromo-6-cyclopropyl-2-methylpyridine 1951411-48-5 C9H10BrN
(2S)-3-(decyloxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid (2S)-3-(decyloxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid 1013997-51-7 C22H23NO4
METHYL (S)-(-)-1-TRITYL-2-AZIRIDINE- METHYL (S)-(-)-1-TRITYL-2-AZIRIDINE- 75154-68-6 C23H21NO2
10-METHYL-9-PHENYLACRIDINIUM PERCHLORATE 10-METHYL-9-PHENYLACRIDINIUM PERCHLORATE 36519-61-6 C20H16ClNO4
2-Fluoro-4-(tetrahydrofuran-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-Fluoro-4-(tetrahydrofuran-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2222996-82-7 C15H21BFNO3
(R)-4-Oxopyrrolidine-2-carboxylic acid (R)-4-Oxopyrrolidine-2-carboxylic acid 911284-93-0 C5H7NO3
Pyridine, 2,5-bis(2,3-difluorophenyl)- Pyridine, 2,5-bis(2,3-difluorophenyl)- 1261483-09-3 C17H9F4N
2-Pyridinemethanol, 3-bromo-α-methyl-, (αS)- 2-Pyridinemethanol, 3-bromo-α-methyl-, (αS)- 317845-81-1 C7H8BrNO
2-fluoropyridine-3,4,5,6-d4 2-fluoropyridine-3,4,5,6-d4 2363789-45-9 C5H4FN
Mal-amido-(CH2COOH)2 Mal-amido-(CH2COOH)2 207613-14-7 C11H12N2O7
1,3,5-Triazin-2(1H)-one, 4,6-dimethyl- 1,3,5-Triazin-2(1H)-one, 4,6-dimethyl- 30885-99-5 C5H7N3O
1,5:6,10-Dimethanooxepino[4,5-d]oxepin-2,4,7,9(1H,5H)-tetrone, tetrahydro- 1,5:6,10-Dimethanooxepino[4,5-d]oxepin-2,4,7,9(1H,5H)-tetrone, tetrahydro- 4945-72-6 C12H10O6
2(1H)-Pyridinone, 5-fluoro-4-methyl- 2(1H)-Pyridinone, 5-fluoro-4-methyl- 1227594-48-0 C6H6FNO
2,4(1H,3H)-Pyrimidinedione, 1-(4-bromophenyl)dihydro- 2,4(1H,3H)-Pyrimidinedione, 1-(4-bromophenyl)dihydro- 90772-28-4 C10H9BrN2O2
Pyridine, 2-chloro-6-(difluoromethyl)-4-iodo- Pyridine, 2-chloro-6-(difluoromethyl)-4-iodo- 1805033-06-0 C6H3ClF2IN
Pyrido[2,3-d]pyrimidine, 4-bromo- Pyrido[2,3-d]pyrimidine, 4-bromo- 1161763-14-9 C7H4BrN3
4-chloro-6-methyl-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine 4-chloro-6-methyl-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine 1258650-41-7 C8H10ClN3
Thiazolo[5,4-d]pyrimidin-5-amine, 7-chloro- Thiazolo[5,4-d]pyrimidin-5-amine, 7-chloro- 1211527-74-0 C5H3ClN4S
5-Bromo-2-methyloxazole 5-Bromo-2-methyloxazole 1391740-17-2 C4H4BrNO
4-bromo-3-iodopyridin-2-ol 4-bromo-3-iodopyridin-2-ol 2294947-91-2 C5H3BrINO
6-Bromo-1H-indole 6-Bromo-1H-indole 52415-29-9 C8H6BrN
4-Hydroxymethylthiazole 4-Hydroxymethylthiazole 7036-04-6 C4H5NOS
1-Boc-4-cyanopiperidine 1-Boc-4-cyanopiperidine 91419-52-2 C11H18N2O2
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