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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
3,3'-Bi(1H-pyrazole) 3,3'-Bi(1H-pyrazole) 2384-02-3 C6H6N4
CHEMBRDG-BB 6423830 CHEMBRDG-BB 6423830 83490-13-5 C13H10N2O2
1-CBZ-3-HYDROXYMETHYLPYRROLIDINE 1-CBZ-3-HYDROXYMETHYLPYRROLIDINE 315718-05-9 C13H17NO3
ovo/FU ovo/FU
SGC7901/FU SGC7901/FU
5-Ethoxy-3-methyl-1-phenylpyrazole 5-Ethoxy-3-methyl-1-phenylpyrazole 1016-41-7 C12H14N2O
1H-Benzimidazole,1-methyl-6-nitro-(9CI) 1H-Benzimidazole,1-methyl-6-nitro-(9CI) 5381-79-3 C8H7N3O2
3-Pyridinecarboxylicacid,1,4-dihydro-1-methyl-,methylester(9CI) 3-Pyridinecarboxylicacid,1,4-dihydro-1-methyl-,methylester(9CI) 59138-83-9 C8H11NO2
Ethyl 5-Bromoindole-2-carboxylate Ethyl 5-Bromoindole-2-carboxylate 16732-70-0 C11H10BrNO2
1H-Imidazole-5-carbonitrile,4-amino-1-methyl-(9CI) 1H-Imidazole-5-carbonitrile,4-amino-1-methyl-(9CI) 40637-80-7 C5H6N4
3-bromo-1-methyl-1H-pyrazole 3-bromo-1-methyl-1H-pyrazole 151049-87-5 C4H5BrN2
3-(4-fluorobenzoyl)tropane 3-(4-fluorobenzoyl)tropane 96920-56-8 C15H18FNO
3,4,5-Tribromopyrazole 3,4,5-Tribromopyrazole 17635-44-8 C3HBr3N2
7-Bromoindole-2-carboxylic acid 7-Bromoindole-2-carboxylic acid 16732-71-1 C9H6BrNO2
6-BROMOIMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 6-BROMOIMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 749849-14-7 C8H5BrN2O2
1-Tritylpyrazole 1-Tritylpyrazole 95163-43-2 C22H18N2
4-HYDRAZINOPYRIDINE dihydrochloride 4-HYDRAZINOPYRIDINE dihydrochloride C5H9Cl2N3
2-(tert-butoxycarbonylamino)pyridine-5-boronic acid, pinacol ester 2-(tert-butoxycarbonylamino)pyridine-5-boronic acid, pinacol ester 910462-31-6 C16H25BN2O4
2-Quinazolinamine 2-Quinazolinamine 1687-51-0 C8H7N3
S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid 1255936-24-3 C13H14BrN3
6-bromo-4-methoxypyrazolo[1,5-a]pyridine-3-carbonitrile 6-bromo-4-methoxypyrazolo[1,5-a]pyridine-3-carbonitrile 1207836-10-9 C9H6BrN3O
8-Azaspiro[Bicyclo[3.2.1]Octane-3,4'-Imidazolidine]-2',5'-Dione 8-Azaspiro[Bicyclo[3.2.1]Octane-3,4'-Imidazolidine]-2',5'-Dione 77398-55-1 C9H14ClN3O2
trimorpholylmethane trimorpholylmethane 22630-09-7 C13H25N3O3
2,5-Pyrrolidinedione, 1-[(4-chlorobenzoyl)oxy]- 2,5-Pyrrolidinedione, 1-[(4-chlorobenzoyl)oxy]- 68388-09-0 C11H8ClNO4
3-Pyrrolidinol, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-, (3R,5S)- 3-Pyrrolidinol, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-, (3R,5S)- 260417-94-5 C11H25NO2Si
2,3-Dibromo-5,6,7,8-tetrahydroimidazo-[1,2-a]pyridine 2,3-Dibromo-5,6,7,8-tetrahydroimidazo-[1,2-a]pyridine 156817-73-1 C7H8Br2N2
4-Chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine 4-Chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine 870706-47-1 C9H10ClN3
Thiazolo[4,5-d]pyrimidin-2-amine, 7-chloro-5-[[(1S)-1-phenylethyl]thio]- Thiazolo[4,5-d]pyrimidin-2-amine, 7-chloro-5-[[(1S)-1-phenylethyl]thio]- 911820-08-1 C13H11ClN4S2
2,4,6-tris(4-pyrazol-1-yl)-1,3,5-triazine 2,4,6-tris(4-pyrazol-1-yl)-1,3,5-triazine 27257-90-5 C12H9N9
Atogepant (MK-8031) Atogepant (MK-8031) 1374248-81-3 C29H23F6N5O3
4-Phenyl-2(3H)-thiazolone 4-Phenyl-2(3H)-thiazolone 3884-31-9 C9H7NOS
6-Nitroindazole 6-Nitroindazole 7597-18-4 C7H5N3O2
8-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyridine 8-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyridine 1206981-68-1 C8H4BrF3N2
5-CYCLOPROPYL-2H-PYRAZOL-3-YLAMINE 5-CYCLOPROPYL-2H-PYRAZOL-3-YLAMINE 175137-46-9 C6H9N3
5-FLUORO-1H-BENZIMIDAZOLE-2-AMINE 5-FLUORO-1H-BENZIMIDAZOLE-2-AMINE 30486-73-8 C7H6FN3
1,3-BIS(4-CHLOROPHENYL)IMIDAZOLIUM CHLORIDE 1,3-BIS(4-CHLOROPHENYL)IMIDAZOLIUM CHLORIDE 141556-46-9 C15H11Cl3N2
4-bromo-2,1,3-benzothiadiazole 4-bromo-2,1,3-benzothiadiazole 22034-13-5 C6H3BrN2S
2-Chloro-6-fluorobenzothiazole 2-Chloro-6-fluorobenzothiazole 399-74-6 C7H3ClFNS
6-IODO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 6-IODO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID 478040-59-4 C8H5IN2O2
2,6-Bis[(4S)-phenyl-2-oxazolin-2-yl]pyridine 2,6-Bis[(4S)-phenyl-2-oxazolin-2-yl]pyridine 174500-20-0 C23H19N3O2
STYRENE MALEIC ANHYDRIDE COPOLYMER STYRENE MALEIC ANHYDRIDE COPOLYMER 9011-13-6 (C8H8.C4H2O3)x
Benzo[b]naphtho[2,1-d]furan, 8-bromo- Benzo[b]naphtho[2,1-d]furan, 8-bromo- 1627917-20-7 C16H9BrO
4-(2-METHYLIMIDAZOL-1-YLMETHYL)PHENYLAMINE 4-(2-METHYLIMIDAZOL-1-YLMETHYL)PHENYLAMINE 772311-98-5 C11H13N3
6-CHLORO-1,3-DIHYDRO-2H-IMIDAZO[4,5-B]PYRIDINE-2-THIONE 6-CHLORO-1,3-DIHYDRO-2H-IMIDAZO[4,5-B]PYRIDINE-2-THIONE 19918-37-7 C6H4ClN3S
3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE 3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE 29096-60-4 C10H10N2O
2,4,7-TRICHLOROQUINAZOLINE 2,4,7-TRICHLOROQUINAZOLINE 6625-94-1 C8H3Cl3N2
2-METHYL-2-PYRROLIDIN-1-YLPROPAN-1-OL 2-METHYL-2-PYRROLIDIN-1-YLPROPAN-1-OL 101258-96-2 C8H17NO
1-(2-bromoethyl)pyrrolidine-2,5-dione 1-(2-bromoethyl)pyrrolidine-2,5-dione 55943-72-1 C6H8BrNO2
3-chloro-2-methoxybenzoic acid 3-chloro-2-methoxybenzoic acid 3260-93-3 C8H7ClO3
IMIDAZO[1,2-A]PYRIDIN-2-AMINE, 7-BROMO- IMIDAZO[1,2-A]PYRIDIN-2-AMINE, 7-BROMO- 865604-33-7 C7H6BrN3
ethyl 6-iodoH-imidazo[1,2-a]pyridine-2-carboxylate ethyl 6-iodoH-imidazo[1,2-a]pyridine-2-carboxylate 214958-32-4 C10H9IN2O2
2-(4-FLUORO-PHENYL)-IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE 2-(4-FLUORO-PHENYL)-IMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE 425658-37-3 C14H9FN2O
2,3-Dibromo-4-(trifluoromethyl)pyridine 2,3-Dibromo-4-(trifluoromethyl)pyridine 1099598-01-2 C6H2Br2F3N
(R)-1-BENZYL-PYRROLIDINE-3-CARBOXYLIC ACID (R)-1-BENZYL-PYRROLIDINE-3-CARBOXYLIC ACID 1082055-65-9 C12H15NO2
1H-Benzimidazole-6-carboxaldehyde, 1-methyl- (9CI) 1H-Benzimidazole-6-carboxaldehyde, 1-methyl- (9CI) 181867-19-6 C9H8N2O
(S)-2-AMINOMETHYL-1-N-CBZ-PYRROLIDINE
(S)-2-AMINOMETHYL-1-N-CBZ-PYRROLIDINE 141774-68-7 C13H18N2O2
Hexamethylol melamine Hexamethylol melamine C9H22N6O6
2,2'-Bioxazole, 4,4',5,5'-tetrahydro-4,4'-di-2-naphthalenyl-, (4S,4'S)- 2,2'-Bioxazole, 4,4',5,5'-tetrahydro-4,4'-di-2-naphthalenyl-, (4S,4'S)- 2567868-01-1 C26H20N2O2
4-CHLORO-5-METHYL-1H-PYRROLO[2,3-B]PYRIDINE 4-CHLORO-5-METHYL-1H-PYRROLO[2,3-B]PYRIDINE 1020056-56-7 C8H7ClN2
A549/FU A549/FU
5-Chloroimidazo[1,2-a]pyridine-2-carboxylic acid 5-Chloroimidazo[1,2-a]pyridine-2-carboxylic acid 1000017-93-5 C8H5ClN2O2
3-Pyrrolidinemethanamine,N-cyclopropyl-4-fluoro-,(3R,4S)-(9CI) 3-Pyrrolidinemethanamine,N-cyclopropyl-4-fluoro-,(3R,4S)-(9CI) 604798-54-1 C8H15FN2
1H-Benzimidazol-5-amine,4-chloro-6-fluoro-(9CI) 1H-Benzimidazol-5-amine,4-chloro-6-fluoro-(9CI) 117275-51-1 C7H5ClFN3
1H-Benzimidazole,2-(2-pyrrolidinyl)-,(R)-(9CI) 1H-Benzimidazole,2-(2-pyrrolidinyl)-,(R)-(9CI) 175530-90-2 C11H13N3
1H-Benzimidazol-2-amine,4,6-dimethyl-(9CI) 1H-Benzimidazol-2-amine,4,6-dimethyl-(9CI) 67469-39-0 C9H11N3
4-PHENYLPYRAZOLE 4-PHENYLPYRAZOLE 10199-68-5 C9H8N2
4-Bromoquinazoline 4-Bromoquinazoline 354574-59-7 C8H5BrN2
1,3-Dimethyl-5-hydroxypyrazole 1,3-Dimethyl-5-hydroxypyrazole 5203-77-0 C5H8N2O
3-Amino-5-cyclobutyl-1H-pyrazole 3-Amino-5-cyclobutyl-1H-pyrazole 326827-21-8 C7H11N3
7-BROMO-2-METHYLQUINAZOLINE 7-BROMO-2-METHYLQUINAZOLINE 552331-87-0 C9H7BrN2
2-Chloro-7-fluoroquinazoline 2-Chloro-7-fluoroquinazoline 956101-10-3 C8H4ClFN2
Cyclopropanecarboxylic acid [4-(4,6-dichloropyrimidin-2-ylsulfanyl)phenyl]amide Cyclopropanecarboxylic acid [4-(4,6-dichloropyrimidin-2-ylsulfanyl)phenyl]amide 639090-53-2 C14H11Cl2N3OS
4-AMINO-3-FORMYLPYRIDINE HCL 4-AMINO-3-FORMYLPYRIDINE HCL 927891-97-2 C6H6N2O·HCl
N-(2,2,2-trifluoroethyl)pyrrolidine-2-carboxamide hydrochloride N-(2,2,2-trifluoroethyl)pyrrolidine-2-carboxamide hydrochloride 1078163-20-8 C7H12ClF3N2O
6-Bromoquinazoline 6-Bromoquinazoline 89892-21-7 C8H5BrN2
2-bromo-3H-imidazo[4,5-c]pyridine 2-bromo-3H-imidazo[4,5-c]pyridine 1557344-85-0 C6H4BrN3
5-(Aminomethyl)-5-(4-fluorophenyl)imidazolidine-2,4-dione hydrochloride 5-(Aminomethyl)-5-(4-fluorophenyl)imidazolidine-2,4-dione hydrochloride 1224885-25-9 C10H11ClFN3O2
 4-chloro-7-fluoro-quinazoline 4-chloro-7-fluoro-quinazoline 16499-62-0 C8H4ClFN2
3-(Benzo[d][1,3]dioxol-5-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 3-(Benzo[d][1,3]dioxol-5-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 61962-84-3 C13H9N3O3
6'-bromo-8'-chloro-1'H-spiro[cyclobutane-1,3'-imidazo[1,5-a]pyridine]-1',5'(2'H)-dione 6'-bromo-8'-chloro-1'H-spiro[cyclobutane-1,3'-imidazo[1,5-a]pyridine]-1',5'(2'H)-dione 1849592-10-4 C10H8BrClN2O2
7-Methyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid 7-Methyl-2-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid 874830-65-6 C10H7F3N2O2
Thieno[2,3-d]pyrimidine-6-carbaldehyde Thieno[2,3-d]pyrimidine-6-carbaldehyde 655253-72-8 C7H4N2OS
Benzyl [(1R,2R)-1-Hydroxy-1-phenyl-3-(1-pyrrolidinyl)-2-propanyl]carbamate Benzyl [(1R,2R)-1-Hydroxy-1-phenyl-3-(1-pyrrolidinyl)-2-propanyl]carbamate 193545-67-4 C21H26N2O3
4-BROMO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE 4-BROMO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE 497832-99-2 C5H4BrF3N2
Imidazo[1,2-a]pyrimidine Imidazo[1,2-a]pyrimidine 274-95-3 C6H5N3
2-ETHYL-4,4-DIMETHYL-2-OXAZOLINE 2-ETHYL-4,4-DIMETHYL-2-OXAZOLINE 5146-88-3 C7H13NO
Alflutinib Alflutinib 1869057-83-9 C28H31F3N8O2
1-(4-FLUOROPHENYL)IMIDAZOLINE-2-THIONE 1-(4-FLUOROPHENYL)IMIDAZOLINE-2-THIONE 17452-07-2 C9H7FN2S
3-methyl-1H-1,2,4-triazole-5-thiol 3-methyl-1H-1,2,4-triazole-5-thiol 7271-44-5 C3H5N3S
1,3,7-TRIAZA-SPIRO[4.5]DECANE-2,4-DIONE 1,3,7-TRIAZA-SPIRO[4.5]DECANE-2,4-DIONE 78222-09-0 C7H11N3O2
4-CHLORO-2-METHYLTHIOPYRAZOLO[1,5-A]1,3,5-TRIAZINE 4-CHLORO-2-METHYLTHIOPYRAZOLO[1,5-A]1,3,5-TRIAZINE 54346-19-9 C6H5ClN4S
L-CIS-PYRROLIDINE-2,4-DICARBOXYLIC ACID L-CIS-PYRROLIDINE-2,4-DICARBOXYLIC ACID 64927-38-4 C6H9NO4
RPA 202248 RPA 202248 143701-75-1 C15H12F3NO4S
1-Bromo-7-chlorodibenzo[b,d]furan 1-Bromo-7-chlorodibenzo[b,d]furan 2173555-52-5 C12H6BrClO
8-bromo-5-methyl-[1,2,4]triazolo[4,3-a]pyridine 8-bromo-5-methyl-[1,2,4]triazolo[4,3-a]pyridine 1379355-21-1 C7H6BrN3
(1R,2S,3S)-2-ethoxymethyl-3-(3,4-dichlorophenyl)-tropane (1R,2S,3S)-2-ethoxymethyl-3-(3,4-dichlorophenyl)-tropane
10-chloronaphtho[2,1-b]benzofuran 10-chloronaphtho[2,1-b]benzofuran 2140822-95-1 C16H9ClO
3-bromo-7-chlorodibenzo[b,d]furan 3-bromo-7-chlorodibenzo[b,d]furan 2244910-28-7 C12H6BrClO
1-((1H-pyrazol-1-yl)methyl)-1H-pyrazole 1-((1H-pyrazol-1-yl)methyl)-1H-pyrazole 27258-04-4 C7H8N4
6-(Tert-butylsulfonyl)-3-iodo-7-methoxyimidazo[1,2-a]pyridine 6-(Tert-butylsulfonyl)-3-iodo-7-methoxyimidazo[1,2-a]pyridine 2141961-59-1 C12H15IN2O3S
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