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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
(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile (R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile 1146629-84-6 C17H26BN3O2
2,3-Bis(benzyloxy)pyridine 2,3-Bis(benzyloxy)pyridine 1228665-98-2 C19H17NO2
2-Chloro-6-isopropylnicotinonitrile 2-Chloro-6-isopropylnicotinonitrile 108244-44-6 C9H9ClN2
6-Chloro-5-nitroimidazo[2,1-b][1,3]thiazole 6-Chloro-5-nitroimidazo[2,1-b][1,3]thiazole 23576-89-8 C5H2ClN3O2S
4-CHLORO-3H-IMIDAZO[4,5-C]PYRIDINE 4-CHLORO-3H-IMIDAZO[4,5-C]PYRIDINE 81053-66-9 C6H4ClN3
4-BROMO-6-FLUORO (1H)INDAZOLE 4-BROMO-6-FLUORO (1H)INDAZOLE 885520-35-4 C7H4BrFN2
1-tert-butyl-5-chloro-1H-pyrazole-4-carbonitrile 1-tert-butyl-5-chloro-1H-pyrazole-4-carbonitrile 1050619-87-8 C8H10ClN3
Pd(IPr)(acac)Cl Pd(IPr)(acac)Cl 868705-03-7 C32H43ClN2O2Pd
1-(DiMethylsulfaMoyl)pyrazole 1-(DiMethylsulfaMoyl)pyrazole 133228-21-4 C5H9N3O2S
S-2-(CBZ-AMINOMETHYL)PYRROLIDINE-HCl S-2-(CBZ-AMINOMETHYL)PYRROLIDINE-HCl 1033245-45-2 C13H19ClN2O2
6-BroMo-2-chloro-8-fluoroquinazoline 6-BroMo-2-chloro-8-fluoroquinazoline 953039-25-3 C8H3BrClFN2
1H-Indole, 5-broMo-4-fluoro- 1H-Indole, 5-broMo-4-fluoro- 344790-96-1 C8H5BrFN
1H-Pyrazolo[4,3-d]pyriMidine, 5-chloro- 1H-Pyrazolo[4,3-d]pyriMidine, 5-chloro- 633328-98-0 C5H3ClN4
(3R,5R)-5-Methylpyrrolidin-3-ol hydrochloride (3R,5R)-5-Methylpyrrolidin-3-ol hydrochloride 857651-11-7 C5H12ClNO
2-aMino-3-(2-Methoxybenzoyl)-5-broMopyridine 2-aMino-3-(2-Methoxybenzoyl)-5-broMopyridine 875639-76-2 C13H11BrN2O2
(3R)-1-Methyl-3-PyrrolidinaMine hydrochloride (3R)-1-Methyl-3-PyrrolidinaMine hydrochloride 403712-80-1 C5H13ClN2
IMidazo[1,2-a]pyridine, 6-fluoro-2-phenyl- IMidazo[1,2-a]pyridine, 6-fluoro-2-phenyl- 1126635-20-8 C13H9FN2
5-Oxa-2-aza-spiro[3.4]octane 5-Oxa-2-aza-spiro[3.4]octane 145309-24-6 C6H11NO
(1H,1H,2H,2H-PERFLUORO-N-HEXYL)METHYLDICHLORO-SILANE (1H,1H,2H,2H-PERFLUORO-N-HEXYL)METHYLDICHLORO-SILANE 38436-16-7 C7H7Cl2F9Si
(2R,4S)-1-FMoc-4-BOC-aMino Pyrrolidine-2-carboxylic acid (2R,4S)-1-FMoc-4-BOC-aMino Pyrrolidine-2-carboxylic acid 1820570-42-0 C25H28N2O6
1-Ethyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide 1-Ethyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide 223436-99-5 C9H16F6N2O4S2
2-(3,4-diMethoxybenzyl)-7-((2S,3S)-2-hydroxy-6-phenylhexan-3-yl)-5-MethyliMidazo[1,5-f][1,2,4]triazin-4(3H)-one 2-(3,4-diMethoxybenzyl)-7-((2S,3S)-2-hydroxy-6-phenylhexan-3-yl)-5-MethyliMidazo[1,5-f][1,2,4]triazin-4(3H)-one 439083-91-7 C27H32N4O4
2-broMo-5-iodoiMidazo[2,1-b]thiazole 2-broMo-5-iodoiMidazo[2,1-b]thiazole 1379307-48-8 C5H2BrIN2S
2-Oxa-6-azaspiro[3.3]heptane-6-ethanaMine 2-Oxa-6-azaspiro[3.3]heptane-6-ethanaMine 54384-40-6 C7H14N2O
3-BroMo-8-Methyl-iMidazo[1,2-a]pyridine-2-carboxylic acid 3-BroMo-8-Methyl-iMidazo[1,2-a]pyridine-2-carboxylic acid 1313712-29-6 C9H7BrN2O2
IMidazo[1,2-a]pyriMidine hydrochloride IMidazo[1,2-a]pyriMidine hydrochloride 6840-21-7 C6H6ClN3
1-propenyl-3-MethyliMidazoliuM perchlorate 1-propenyl-3-MethyliMidazoliuM perchlorate 1366043-39-1 C7H11ClN2O4
1H-lMidazoliuM,2-[[(4S,5S)-1,3-diMiethyl-4,5-diphenyl-2-iMidazolinydene]aMino]-4,5-dihydro-1,3-diMethyl-4,5-diphenyl-,choride(1:1),(4S,5S)- 1H-lMidazoliuM,2-[[(4S,5S)-1,3-diMiethyl-4,5-diphenyl-2-iMidazolinydene]aMino]-4,5-dihydro-1,3-diMethyl-4,5-diphenyl-,choride(1:1),(4S,5S)- 1268449-00-8 C34H36ClN5
2-cyclobutylpyridin-4-aMine 2-cyclobutylpyridin-4-aMine 1159818-59-3 C9H12N2
3-cyclobutylpyridin-4-aMine 3-cyclobutylpyridin-4-aMine 1374664-56-8 C9H12N2
2-(4-Bromophenyl)-4-phenylquinazoline 2-(4-Bromophenyl)-4-phenylquinazoline 540466-42-0 C20H13BrN2
2(1H)-Pyridinone, 6-cyclohexyl 2(1H)-Pyridinone, 6-cyclohexyl 1159814-04-6 C11H15NO
6-BroMo-7-azaindole-3-carboxylic acid Methyl ester 6-BroMo-7-azaindole-3-carboxylic acid Methyl ester 1342811-51-1 C9H7BrN2O2
4-Chloro-5,6-diMethyl-7H-pyrrolo[2,3-d]pyriMidine 4-Chloro-5,6-diMethyl-7H-pyrrolo[2,3-d]pyriMidine 82703-38-6 C8H8ClN3
(R)-N-(2-oxo-2-(pyrrolidin-3-ylaMino)-ethyl)-3-(trifluoroMethyl)benzaMide (R)-N-(2-oxo-2-(pyrrolidin-3-ylaMino)-ethyl)-3-(trifluoroMethyl)benzaMide 226249-16-7 C14H16F3N3O2
1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole 1-(1-Ethoxyethyl)-4-iodo-1H-pyrazole 575452-22-1 C7H11IN2O
3-(4-BroMophenyl)pyrrolidine hydrochloride 3-(4-BroMophenyl)pyrrolidine hydrochloride 1187931-39-0 C10H13BrClN
7-oxa-1-azaspiro[4.4]nonane  (Hydrochloride) 7-oxa-1-azaspiro[4.4]nonane (Hydrochloride) 1620569-18-7 C7H14ClNO
MethaniMidaMide, N'-[1-cyclopropyl-3-(2-fluoro-4-iodophenyl)-1,2,3,6-tetrahydro-2,6-dioxo-4-pyriMidinyl]-N,N-diMethyl- MethaniMidaMide, N'-[1-cyclopropyl-3-(2-fluoro-4-iodophenyl)-1,2,3,6-tetrahydro-2,6-dioxo-4-pyriMidinyl]-N,N-diMethyl- 871700-30-0 C16H16FIN4O2
Furo[2,3-d]pyriMidine, 4-chloro-5,6-diphenyl- Furo[2,3-d]pyriMidine, 4-chloro-5,6-diphenyl- 65148-07-4 C18H11ClN2O
4-Cyano-2-Methylphenylboronic acid, pinacol ester 4-Cyano-2-Methylphenylboronic acid, pinacol ester 848953-05-9 C14H18BNO2
4-BroMo-1-cyclobutylpyrazole 4-BroMo-1-cyclobutylpyrazole 1002309-50-3 C7H9BrN2
1,4-Di(1H-pyrazol-4-yl)benzene 1,4-Di(1H-pyrazol-4-yl)benzene 1036248-62-0 C12H10N4
6-tert-butyl 3-ethyl 4,5-dihydro-2H-pyrazolo[3,4-c]pyridine-3,6(7H)-dicarboxylate 6-tert-butyl 3-ethyl 4,5-dihydro-2H-pyrazolo[3,4-c]pyridine-3,6(7H)-dicarboxylate 821785-75-5 C14H21N3O4
(E)-1,1,1-Trichloro-4-ethoxy-but-3-en-2-one (E)-1,1,1-Trichloro-4-ethoxy-but-3-en-2-one 59938-07-7 C6H7Cl3O2
1-Boc-3-broMo-1H-pyrrolo[3,2-b]pyridine 1-Boc-3-broMo-1H-pyrrolo[3,2-b]pyridine 192189-15-4 C12H13BrN2O2
9-Boc-3-oxa-7,9-diazabicyclo[3.3.1]nonane 9-Boc-3-oxa-7,9-diazabicyclo[3.3.1]nonane 1251010-45-3 C11H20N2O3
2-(furan-2-yl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-(furan-2-yl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine 2096339-38-5 C15H18BNO3
5-(3-Hydroxypropyl)-2,4(1H,3H)-pyriMidinedione 5-(3-Hydroxypropyl)-2,4(1H,3H)-pyriMidinedione 53761-38-9 C7H10N2O3
3-(piperidin-4-yl)pyridine hydrochloride 3-(piperidin-4-yl)pyridine hydrochloride 690261-73-5 C10H15ClN2
3-BroMo-5,6,7,8-tetrahydro-1,7-naphthyridine 3-BroMo-5,6,7,8-tetrahydro-1,7-naphthyridine 1196156-01-0 C8H9BrN2
4-BroMo-1H-iMidazole-2-carboxylic acid 4-BroMo-1H-iMidazole-2-carboxylic acid 1260753-02-3 C4H3BrN2O2
4-BroMo-7-chloro-1H-indazole 4-BroMo-7-chloro-1H-indazole 1186334-61-1 C7H4BrClN2
4-Methoxyindole 4-Methoxyindole 4837-90-5 C9H9NO
4-broMo-6,7-diMethoxycinnoline 4-broMo-6,7-diMethoxycinnoline 879014-17-2 C10H9BrN2O2
6-Chloro-1-Methyl-1H-iMidazo[4,5-c]pyridine 6-Chloro-1-Methyl-1H-iMidazo[4,5-c]pyridine 7205-46-1 C7H6ClN3
4-Bromo-2-(iso-propoxy)thiazole 4-Bromo-2-(iso-propoxy)thiazole 1159814-09-1 C6H8BrNOS
6-(furan-3-yl)pyridin-2-amine 6-(furan-3-yl)pyridin-2-amine 1124382-91-7 C9H8N2O
(2S)-N-[(1S,2R)-2-hydroxy-1,2-diphenylethyl]-2-Pyrrolidinecarboxamide (2S)-N-[(1S,2R)-2-hydroxy-1,2-diphenylethyl]-2-Pyrrolidinecarboxamide 529486-25-7 C19H22N2O2
ethyl 2-(3-((pyrrolidin-1-yl)methyl)benzylamino)acetate ethyl 2-(3-((pyrrolidin-1-yl)methyl)benzylamino)acetate 1228587-58-3 C16H24N2O2
tert-butyl 7-amino-2-azaspiro[3.5]nonane-2-carboxylate tert-butyl 7-amino-2-azaspiro[3.5]nonane-2-carboxylate 1408075-19-3 C13H24N2O2
(R)-2-Acetyl-pyrrolidine hydrochloride (R)-2-Acetyl-pyrrolidine hydrochloride 1373232-21-3 C6H12ClNO
7-HYDROXY-5-METHYL-2-METHYLTHIO-S-TRIAZOLO[1,5-A]PYRIMIDINE 7-HYDROXY-5-METHYL-2-METHYLTHIO-S-TRIAZOLO[1,5-A]PYRIMIDINE 40775-78-8 C7H8N4OS
5-PHENYL-1H-1,2,3-TRIAZOLE 5-PHENYL-1H-1,2,3-TRIAZOLE 1680-44-0 C8H7N3
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbonitrile 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbonitrile 1111096-21-9 C11H14BNO3
3-Methylpiperidin-4-one hydrochloride 3-Methylpiperidin-4-one hydrochloride 4629-78-1 C6H12ClNO
5-Bromo-2-(cyclohexyl)pyrimidine 5-Bromo-2-(cyclohexyl)pyrimidine 1215072-92-6 C10H13BrN2
4-fluoro-2,4'-bipyridine 4-fluoro-2,4'-bipyridine 1214378-19-4 C10H7FN2
7-Chloro-3-iodoimidazo(1,2-B)pyridazine 7-Chloro-3-iodoimidazo(1,2-B)pyridazine 1383481-13-7 C6H3ClIN3
2-(4-methoxyphenyl)-1,3-thiazole 2-(4-methoxyphenyl)-1,3-thiazole 27088-84-2 C10H9NOS
3-Bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide 3-Bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide 1788044-16-5 C7H9Br2NS
5-bromo-N-butyl-7-((1r,4r)-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine 5-bromo-N-butyl-7-((1r,4r)-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine 1429882-29-0 C22H37BrN4OSi
1-Octyl-1H-benzo[d]imidazole 1-Octyl-1H-benzo[d]imidazole 42032-46-2 C15H22N2
5-FLUORO-2-METHYLBENZIMIDAZOLE 5-FLUORO-2-METHYLBENZIMIDAZOLE 118469-15-1 C8H7FN2
2-Bromo-6-methoxy-4-(trifluoromethyl)pyridine 2-Bromo-6-methoxy-4-(trifluoromethyl)pyridine 1211536-10-5 C7H5BrF3NO
3-Methyl-6-(trifluoromethyl)imidazo[2,1-b]thiazole-5-carboxylic acid 3-Methyl-6-(trifluoromethyl)imidazo[2,1-b]thiazole-5-carboxylic acid 1368302-66-2 C8H5F3N2O2S
6-isopropoxypyridin-2-amine 6-isopropoxypyridin-2-amine 957236-87-2 C8H12N2O
2-bromo-1H-imidazole-5-carboxylic acid 2-bromo-1H-imidazole-5-carboxylic acid 944901-01-3 C4H3BrN2O2
5-(bromomethyl)pyrazolo[1,5-a]pyrimidine 5-(bromomethyl)pyrazolo[1,5-a]pyrimidine 1228351-80-1 C7H6BrN3
2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-Imidazo[1,2-a]pyridine 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-Imidazo[1,2-a]pyridine 1352391-12-8 C14H19BN2O2
1-tert-butyl 2-ethyl 5-oxopyrrolidine-1,2-dicarboxylate 1-tert-butyl 2-ethyl 5-oxopyrrolidine-1,2-dicarboxylate 251924-83-1 C12H19NO5
3-cyclohexyl-2(1H)-Pyridinone 3-cyclohexyl-2(1H)-Pyridinone 50549-33-2 C11H15NO
3-bromoimidazo[5,1-b]thiazole 3-bromoimidazo[5,1-b]thiazole 1279721-68-4 C5H3BrN2S
5-(prop-1-en-2-yl)pyridin-3-amine 5-(prop-1-en-2-yl)pyridin-3-amine 1321594-86-8 C8H10N2
2-methyl-4-(piperidin-3-yl)pyridine dihydrochloride 2-methyl-4-(piperidin-3-yl)pyridine dihydrochloride 1260822-49-8 C11H16N2
1H-Benzimidazole, 1-(4-bromophenyl)-2-ethyl- 1H-Benzimidazole, 1-(4-bromophenyl)-2-ethyl- 97870-64-9 C15H13BrN2
2-[(tert-butoxy)carbonyl]-2-azabicyclo[2.2.1]heptane-5-carboxylic acid 2-[(tert-butoxy)carbonyl]-2-azabicyclo[2.2.1]heptane-5-carboxylic acid 1363210-41-6 C12H19NO4
2-bromo-3-chloro-4-(trifluoromethyl)pyridine 2-bromo-3-chloro-4-(trifluoromethyl)pyridine 1211582-91-0 C6H2BrClF3N
2-Amino-6-(trifluoromethyl)pyridine-5-carbonitrile 2-Amino-6-(trifluoromethyl)pyridine-5-carbonitrile 1233243-98-5 C7H4F3N3
2-fluoro-4-(trifluoromethyl)pyridine-3-carbonitrile 2-fluoro-4-(trifluoromethyl)pyridine-3-carbonitrile 1805633-57-1 C7H2F4N2
4,8-dibromo-6-(2-ethylhexyl)-[1,2,5]thiadiazolo[3,4-f]benzotriazole 4,8-dibromo-6-(2-ethylhexyl)-[1,2,5]thiadiazolo[3,4-f]benzotriazole 1307899-44-0 C14H17Br2N5S
2,4-Dichloro-6-methyl-1,3,5-triazine 2,4-Dichloro-6-methyl-1,3,5-triazine 30894-74-7 C6H7Cl2N3
1-(Pyridin-3-yl)-1H-imidazol-2-amine 1-(Pyridin-3-yl)-1H-imidazol-2-amine 1211541-66-0 C8H8N4
2-Amino-5-methylthiazole 2-Amino-5-methylthiazole 7305-71-7 C4H6N2S
1,3,5-Triazine, 2-chloro-4-methoxy- 1,3,5-Triazine, 2-chloro-4-methoxy- 112667-87-5 C4H4ClN3O
3-METHOXY-4-(1,3-OXAZOL-5-YL)ANILINE 3-METHOXY-4-(1,3-OXAZOL-5-YL)ANILINE 198821-79-3 C10H10N2O2
Pyrimidine, 4-chloro-6-methoxy-2-methyl-5-nitro- Pyrimidine, 4-chloro-6-methoxy-2-methyl-5-nitro- 60331-15-9 C6H6ClN3O3
4(1H)-Pyrimidinone, 2-cyclopropyl-6-phenyl- 4(1H)-Pyrimidinone, 2-cyclopropyl-6-phenyl- 651043-20-8 C13H12N2O
2(3H)-Thiophenone, 5-phenyl- 2(3H)-Thiophenone, 5-phenyl- 939-09-3 C10H8OS
3-(tert-butyl)pyridin-2-amine 3-(tert-butyl)pyridin-2-amine 1339700-98-9 C9H14N2
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