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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
2,2'-Bi-1H-imidazole, 1,1'-bis[3-(1,1-dimethylethyl)phenyl]-4,4',5,5'-tetrahydro-4,4'-bis(1-methylethyl)-, (4S,4'S)- 2,2'-Bi-1H-imidazole, 1,1'-bis[3-(1,1-dimethylethyl)phenyl]-4,4',5,5'-tetrahydro-4,4'-bis(1-methylethyl)-, (4S,4'S)- 2374958-80-0 C32H46N4
(R)-4-bromo-1-(pyrrolidin-3-yl)-1H-pyrazole hydrochloride (R)-4-bromo-1-(pyrrolidin-3-yl)-1H-pyrazole hydrochloride 2828444-30-8 C7H11BrClN3
Sodium Benzotriazole Sodium Benzotriazole 148918-02-9
DIAMMONIUM IMIDODISULFATE DIAMMONIUM IMIDODISULFATE 13597-84-7 H9N3O6S2
2-Pyridinecarboxamide, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]amino]-1,2,5,6-tetrahydro-3-methyl-, (2S,5R)- 2-Pyridinecarboxamide, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]amino]-1,2,5,6-tetrahydro-3-methyl-, (2S,5R)- 2209874-01-9 C13H27N3O2Si
Pyridine, 3-(chloromethyl)-2-fluoro- (9CI) Pyridine, 3-(chloromethyl)-2-fluoro- (9CI) 315180-14-4 C6H5ClFN
8-bromo-7-ethylimidazo[1,2-a]pyridine 8-bromo-7-ethylimidazo[1,2-a]pyridine 2227434-20-8 C9H9BrN2
(1,5-CYCLOOCTADIENE)(PYRIDINE)(TRICYCLOHEXYLPHOSPHINE)IRIDIUM(I) HEXAFLUOROPHOSPHATE (1,5-CYCLOOCTADIENE)(PYRIDINE)(TRICYCLOHEXYLPHOSPHINE)IRIDIUM(I) HEXAFLUOROPHOSPHATE 64536-78-3 C31H47F6IrNP2
1-(4-IODOPHENYL)-1H-PYRAZOLE 1-(4-IODOPHENYL)-1H-PYRAZOLE 368869-86-7 C9H7IN2
(R)-1-BOC-2-METHYL-PYRROLIDINE
(R)-1-BOC-2-METHYL-PYRROLIDINE 157007-54-0 C10H19NO2
4-PyriMidinecarboxylic acid, 5-broMo-2-(Methylthio)-, ethyl ester 4-PyriMidinecarboxylic acid, 5-broMo-2-(Methylthio)-, ethyl ester 74840-38-3 C8H9BrN2O2S
2-(4-DIMETHYLAMINO-PHENYL)-1 H-BENZOIMIDAZOL-5-YLAMINE 2-(4-DIMETHYLAMINO-PHENYL)-1 H-BENZOIMIDAZOL-5-YLAMINE 40655-14-9 C15H16N4
10-BroMo-2-iodo-9-Methyl-5,6-dihydrobenzo[f]iMidazo[1,2-d][1,4]oxazepine 10-BroMo-2-iodo-9-Methyl-5,6-dihydrobenzo[f]iMidazo[1,2-d][1,4]oxazepine 1401305-33-6 C12H10BrIN2O
5-BroMo-2-(Methylsulfinyl)pyriMidine 5-BroMo-2-(Methylsulfinyl)pyriMidine 79685-17-9 C5H5BrN2OS
3-[[3,5-bis(trifluoroMethyl)phenyl]aMino]-4-[[(1R,2R)-2-(1-pyrrolidinyl)cyclohexyl]aMino]- 3-[[3,5-bis(trifluoroMethyl)phenyl]aMino]-4-[[(1R,2R)-2-(1-pyrrolidinyl)cyclohexyl]aMino]- 1346683-42-8 C22H23F6N3O2
2-(5-Borono-2-pyrimidinyl)imidodicarbonic acid 1,3-bis(tert-butyl) ester 2-(5-Borono-2-pyrimidinyl)imidodicarbonic acid 1,3-bis(tert-butyl) ester 1360950-40-8 C14H22BN3O6
7-broMo-5,5-diMethyl-5H-indeno[1,2-b]pyridine 7-broMo-5,5-diMethyl-5H-indeno[1,2-b]pyridine 1041263-18-6 C14H12BrN
5-Bromo-2-ethyl-1H-pyrrolo[2,3-b]pyridine 5-Bromo-2-ethyl-1H-pyrrolo[2,3-b]pyridine 1228666-29-2 C9H9BrN2
H-PRO-OET HCL H-PRO-OET HCL 33305-75-8 C7H14ClNO2
3,6-DI-2-PYRIDYL-1,2,4,5-TETRAZINE 3,6-DI-2-PYRIDYL-1,2,4,5-TETRAZINE 1671-87-0 C12H8N6
Tribenzylphosphine(1,5-cyclooctadiene)[1,3-bis(2,4,6-triMethylphenyl)iMidazol-2-ylidene]iridiuM(I) hexafluorophosphate, Min. 98% Tribenzylphosphine(1,5-cyclooctadiene)[1,3-bis(2,4,6-triMethylphenyl)iMidazol-2-ylidene]iridiuM(I) hexafluorophosphate, Min. 98% 1019853-01-0 C50H57F6IrN2P2-
2-(2,4-difluorophenyl)-5-(trifluoroMethyl)pyridine 2-(2,4-difluorophenyl)-5-(trifluoroMethyl)pyridine 387827-64-7 C12H6F5N
(S)-6-(5-(7-broMo-9,9-difluoro-9H-fluoren-2-yl)-1H-iMidazol-2-yl)-5-azaspiro[2.4]heptane hydrochloride (S)-6-(5-(7-broMo-9,9-difluoro-9H-fluoren-2-yl)-1H-iMidazol-2-yl)-5-azaspiro[2.4]heptane hydrochloride 2004675-25-4 C22H19BrClF2N3
2(1H)-PyriMidinone, 4-aMino-1-[(2S)-2-hydroxy-3-(triphenylMethoxy)propyl]- 2(1H)-PyriMidinone, 4-aMino-1-[(2S)-2-hydroxy-3-(triphenylMethoxy)propyl]- 132336-30-2 C26H25N3O3
2-(Pyrimidin-2-yl)benzoic acid 2-(Pyrimidin-2-yl)benzoic acid 400892-62-8 C11H8N2O2
PMK ethyl glycidate PMK ethyl glycidate 28578-16-7 C13H14O5
N-CBZ-trans-4-Hydroxy-D-prolinol N-CBZ-trans-4-Hydroxy-D-prolinol 1448706-36-2 C13H17NO4
(S)-3-Methyl-pyrrolidine-3-carboxylic acid (S)-3-Methyl-pyrrolidine-3-carboxylic acid 1427203-57-3 C6H11NO2
4-(PYRROLIDIN-1-YL)BENZYLAMINE 4-(PYRROLIDIN-1-YL)BENZYLAMINE 114365-04-7 C11H16N2
6-Bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine hydrochloride 6-Bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine hydrochloride 668980-99-2 C9H11BrClN3
Umicore M73 SIMes Umicore M73 SIMes 1025728-57-7 C36H46Cl2N3O3Ru
Dichloro[1,3-bis(2,6-isopropylphenyl)-2-imidazolidinylidene](2-isopropoxyphenylmethylene)ruthenium(II) Dichloro[1,3-bis(2,6-isopropylphenyl)-2-imidazolidinylidene](2-isopropoxyphenylmethylene)ruthenium(II) 635679-24-2 C37H49Cl2N2ORu
5-benzyloctahydro-1H-pyrrolo[3,2-c]pyridine 5-benzyloctahydro-1H-pyrrolo[3,2-c]pyridine 1506066-94-9 C14H20N2
ETHYL 2-(2-FORMYLAMINO-1,3-THIAZOL-4-YL)-2-OXOACETATE ETHYL 2-(2-FORMYLAMINO-1,3-THIAZOL-4-YL)-2-OXOACETATE 64987-03-7 C8H8N2O4S
1-METHYL-4-NITRO-1H-PYRAZOLE 1-METHYL-4-NITRO-1H-PYRAZOLE 82208-47-7 C4H5N3O2
[C2MIm]SbF6 [C2MIm]SbF6 305370-81-4 C6H11F6N2P
(2S,4R)-tert-Butyl 2-(hydroxymethyl)-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate (2S,4R)-tert-Butyl 2-(hydroxymethyl)-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate 148017-07-6 C11H21NO6S
5-chloro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)pyridine 5-chloro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)pyridine 1426337-02-1 C17H19BClNO3
4-Chloro-5-fluoro-6-methoxy-2-methylpyrimidine 4-Chloro-5-fluoro-6-methoxy-2-methylpyrimidine 1383976-40-6 C6H6ClFN2O
4-chloro-6-methoxy-Pyrido[3,2-d]pyrimidine 4-chloro-6-methoxy-Pyrido[3,2-d]pyrimidine 1417555-18-0 C8H6ClN3O
5-iodo-2-Pyridinecarboxamide 5-iodo-2-Pyridinecarboxamide 41960-46-7 C6H5IN2O
6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine 1259512-11-2 C9H11BrN2
2-amino-5-(trifluoromethyl)pyridine-3-carbonitrile 2-amino-5-(trifluoromethyl)pyridine-3-carbonitrile 1211514-97-4 C7H4F3N3
5,6-difluoro-2-(2-hexyldecyl)-2H-benzo[d][1,2,3]triazole 5,6-difluoro-2-(2-hexyldecyl)-2H-benzo[d][1,2,3]triazole 1563332-24-0 C22H35F2N3
(R)-N- (4-(chlorodifluoromethoxy)phenyl)- 6-(3- hydroxypyrrolidin-1- yl)-5- (1H-pyrazol- 5-yl)nicotinamide (R)-N- (4-(chlorodifluoromethoxy)phenyl)- 6-(3- hydroxypyrrolidin-1- yl)-5- (1H-pyrazol- 5-yl)nicotinamide 1492952-76-7 C20H18ClF2N5O3
3,6-dibromo-2-(trifluoromethyl)pyridine 3,6-dibromo-2-(trifluoromethyl)pyridine 1211588-54-3 C6H2Br2F3N
4-(Difluoromethylene)-4,5-dihydro-3H-pyrazole 4-(Difluoromethylene)-4,5-dihydro-3H-pyrazole 88766-66-9 C4H4F2N2
5-Chloro-7-iodo-1H-pyrazolo[3,4-c]pyridine 5-Chloro-7-iodo-1H-pyrazolo[3,4-c]pyridine 1951371-15-5 C6H3ClIN3
(1H-PYRAZOL-3-YL)METHANOL (1H-PYRAZOL-3-YL)METHANOL 23585-49-1 C4H6N2O
6-METHYLIMIDAZO[2,1-B][1,3]THIAZOLE-5-CARBOXYLIC ACID 6-METHYLIMIDAZO[2,1-B][1,3]THIAZOLE-5-CARBOXYLIC ACID 77628-51-4 C7H6N2O2S
N,N'-bis(2,6-bis(diphenylmethyl)-4-methoxyphenyl)imidazolium chloride N,N'-bis(2,6-bis(diphenylmethyl)-4-methoxyphenyl)imidazolium chloride 1416368-03-0 C69H57ClN2O2
1,3,5-Triazine-2,4-dimethoxy-6-(4-morpholinyl)- 1,3,5-Triazine-2,4-dimethoxy-6-(4-morpholinyl)- 241483-00-1 C9H14N4O3
(S,S)-2,2'-METHYLENEBIS(4-PHENYL-2-OXAZOLINE) (S,S)-2,2'-METHYLENEBIS(4-PHENYL-2-OXAZOLINE) 132098-59-0 C19H18N2O2
3-(2-BROMO-PHENYL)-1H-PYRAZOLE 3-(2-BROMO-PHENYL)-1H-PYRAZOLE 114382-20-6 C9H7BrN2
5-Chlorooxindole 5-Chlorooxindole 17630-75-0 C8H6ClNO
1-(3-BROMOBENZYL)PYRROLIDINE 1-(3-BROMOBENZYL)PYRROLIDINE 168820-15-3 C11H14BrN
URIDINE-2',3'-CYCLIC MONOPHOSPHATE SODIUM SALT URIDINE-2',3'-CYCLIC MONOPHOSPHATE SODIUM SALT 15718-50-0 C9H10N2NaO8P
2-Methylindole 2-Methylindole 95-20-5 C9H9N
TERT-BUTYL 2,4-DICHLORO-5H-PYRROLO[3,4-D]PYRIMIDINE-6(7H)-CARBOXYLATE TERT-BUTYL 2,4-DICHLORO-5H-PYRROLO[3,4-D]PYRIMIDINE-6(7H)-CARBOXYLATE 903129-71-5 C11H13Cl2N3O2
tert-butyl (S)-4-(7-chloro-6-fluoro-1-(2-isopropyl-4-methylpyridin-3-yl)-2-oxo-1,2-dihydropyrido[2,3-d]pyrimidin-4-yl)-3-methylpiperazine-1-carboxylate tert-butyl (S)-4-(7-chloro-6-fluoro-1-(2-isopropyl-4-methylpyridin-3-yl)-2-oxo-1,2-dihydropyrido[2,3-d]pyrimidin-4-yl)-3-methylpiperazine-1-carboxylate 2252403-84-0 C26H32ClFN6O3
12H-Benzofuro[2,3-a]carbazole 12H-Benzofuro[2,3-a]carbazole 1338919-70-2 C18H11NO
1-Benzylimidazole-5-carboxylic Acid 1-Benzylimidazole-5-carboxylic Acid 5317-07-7 C11H10N2O2
(R)-5,7-difluorochroman-4-ol (R)-5,7-difluorochroman-4-ol 1270294-05-7 C9H8F2O2
6-bromo-7-chloroquinazoline-2,4-diol 6-bromo-7-chloroquinazoline-2,4-diol 1166378-30-8 C8H4BrClN2O2
2,4,6-tris(3,5-dimethylpyrazol-1-yl)-1,3,5-triazine 2,4,6-tris(3,5-dimethylpyrazol-1-yl)-1,3,5-triazine 154403-27-7 C18H21N9
4,4',4'',4'''-(2,2',6,6'-tetramethoxy-[1,1'-biphenyl]-3,3',5,5'-tetrayl)tetrapyridine 4,4',4'',4'''-(2,2',6,6'-tetramethoxy-[1,1'-biphenyl]-3,3',5,5'-tetrayl)tetrapyridine 1799509-00-4 C36H30N4O4
4,4'-(5'-(4-(pyridin-4-yl)phenyl)-[1,1':3',1''-terphenyl]-4,4''-diyl)dipyridine 4,4'-(5'-(4-(pyridin-4-yl)phenyl)-[1,1':3',1''-terphenyl]-4,4''-diyl)dipyridine 170165-85-2 C39H27N3
4-D-methylthiazolidine-2-thine 4-D-methylthiazolidine-2-thine 114296-85-4 C4H7NS2
2-(Dibenzo[b,d]furan-1-yl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane 2-(Dibenzo[b,d]furan-1-yl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane 1822310-41-7 C18H19BO3
5-Bromo-4-cyclopropyl-6-methoxypyrimidine 5-Bromo-4-cyclopropyl-6-methoxypyrimidine 1649454-57-8 C8H9BrN2O
6-bromo-2,3,8-trimethylimidazo[1,2-a]pyridine 6-bromo-2,3,8-trimethylimidazo[1,2-a]pyridine 1215953-19-7 C10H11BrN2
5-(aminomethyl)-2-pyrrolidinone oxalate 5-(aminomethyl)-2-pyrrolidinone oxalate 1050590-36-7 C7H12N2O5
3-chloro-2-(pyrrolidin-3-yloxy)pyridine 3-chloro-2-(pyrrolidin-3-yloxy)pyridine 817187-51-2 C9H11ClN2O
PS1037 PS1037 908864-14-2 C17H25N5O2
(2S,4R)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride (2S,4R)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride 1448189-90-9 C16H20ClN3O2S
(2R,4S)-4-FLUORO-2-METHYLPYRROLIDINE HCL (2R,4S)-4-FLUORO-2-METHYLPYRROLIDINE HCL 1951424-96-6 C5H11ClFN
ETHYL 2-BROMO-4-CHLORO-1H-IMIDAZOLE-5-CARBOXYLATE ETHYL 2-BROMO-4-CHLORO-1H-IMIDAZOLE-5-CARBOXYLATE 1956318-26-5 C6H6BrClN2O2
6-BROMO-3-METHYLBENZODISOXAZOLE 6-BROMO-3-METHYLBENZODISOXAZOLE 66033-69-0 C8H6BrNO
BOC-D-NVA-OSU BOC-D-NVA-OSU 213178-93-9 C14H22N2O6
2,4-DICHLORO-5-FLUOROQUINAZOLINE 2,4-DICHLORO-5-FLUOROQUINAZOLINE 87611-00-5 C8H3Cl2FN2
6,8-Dibromo-2-trifluoromethylimidazo[1,2-a]pyrazine 6,8-Dibromo-2-trifluoromethylimidazo[1,2-a]pyrazine 1208082-24-9 C7H2Br2F3N3
BOC-4-HYDROXY-L-PYRROLIDINE LACTONE BOC-4-HYDROXY-L-PYRROLIDINE LACTONE 113775-22-7 C10H15NO4
4-(1-BUTENYL PENTENYL) PYRIDINE 4-(1-BUTENYL PENTENYL) PYRIDINE 2057-34-3 C14H19N
5',3'']Terpyridine 5',3'']Terpyridine 106047-31-8 C15H11N3
2,3,4-trimethyl-5,6-diphenylpyridine 2,3,4-trimethyl-5,6-diphenylpyridine 1004547-55-0 C20H19N
MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER 212650-43-6 C10H17NO5
(R)-4-BENZYL-1,3-OXAZOLIDINE-2-THIONE (R)-4-BENZYL-1,3-OXAZOLIDINE-2-THIONE 190970-58-2 C10H11NOS
2-Methyl-4-phenyl-1H-imidazole 2-Methyl-4-phenyl-1H-imidazole 13739-48-5 C10H10N2
1H-1,2,4-Triazole-3,5-diamine 1H-1,2,4-Triazole-3,5-diamine 1455-77-2 C2H5N5
1-(4-Nitrophenyl)-1H-pyrazole 1-(4-Nitrophenyl)-1H-pyrazole 3463-30-7 C9H7N3O2
5-(CHLOROMETHYL)-1,3-DIMETHYL-1H-PYRAZOLE 5-(CHLOROMETHYL)-1,3-DIMETHYL-1H-PYRAZOLE 852227-86-2 C6H9ClN2
(1,3-DIMETHYL-1H-PYRAZOL-5-YL)METHANOL (1,3-DIMETHYL-1H-PYRAZOL-5-YL)METHANOL 57012-20-1 C6H10N2O
5-methyl-1H-4-carboxylic acid 5-methyl-1H-4-carboxylic acid 1457-59-6 C5H6N2O2
3-(1-pyrrolidinyl)propiophenone hydrochloride 3-(1-pyrrolidinyl)propiophenone hydrochloride 833-86-3 C13H17NO.ClH
1-bromo-3-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,5-a]pyrazine hydrochloride 1-bromo-3-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,5-a]pyrazine hydrochloride 2138351-97-8 C7H8BrClF3N3
4,5-dihydro-2-(2-methoxyphenyl)-1-[2-(2-methoxyphenyl)-4,5-diphenyl-2H-imidazol-2-yl]-1H-imidazole 4,5-dihydro-2-(2-methoxyphenyl)-1-[2-(2-methoxyphenyl)-4,5-diphenyl-2H-imidazol-2-yl]-1H-imidazole 7292-18-4 C32H28N4O2
1-(methoxymethyl)-1H-imidazole 1-(methoxymethyl)-1H-imidazole 20075-26-7 C5H8N2O
1-(tert-butyl)pyrrolidin-2-one 1-(tert-butyl)pyrrolidin-2-one 20687-53-0 C8H15NO
N-acetylsulphanilic acid N-acetylsulphanilic acid 121-62-0 C8H9NO4S
1-methyl-5-thioxopyrrolidin-2-one 1-methyl-5-thioxopyrrolidin-2-one 2043-24-5 C5H7NOS
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