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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-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
2H-1,2,3-Triazole-2-ethanol, 4-bromo- 2H-1,2,3-Triazole-2-ethanol, 4-bromo- 2059948-64-8 C4H6BrN3O
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
1,2,3-THIADIAZOLE-4-CARBOXYLIC ACID 1,2,3-THIADIAZOLE-4-CARBOXYLIC ACID 4100-13-4 C3H2N2O2S
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
7-HYDROXYBENZOFURAN 7-HYDROXYBENZOFURAN 4790-81-2 C8H6O2
2,3-Dihydro-2,2-dimethyl-7-benzofuranol 2,3-Dihydro-2,2-dimethyl-7-benzofuranol 1563-38-8 C10H12O2
Benzoguanamine Benzoguanamine 91-76-9 C9H9N5
Piperonyl aldehyde Piperonyl aldehyde 120-57-0 C8H6O3
Pseudothiohydantoin Pseudothiohydantoin 556-90-1 C3H4N2OS
Clopidol Clopidol 2971-90-6 C7H7Cl2NO
2-Amino-3,5-dinitrothiophene 2-Amino-3,5-dinitrothiophene 2045-70-7 C4H3N3O4S
FLUORENE-D10 FLUORENE-D10 81103-79-9 C13D10
3-Quinuclidinyl benzilate 3-Quinuclidinyl benzilate 6581-06-2 C21H23NO3
ISOSAFROLE ISOSAFROLE 120-58-1 C10H10O2
Pridine pury Pridine pury
Safrole Safrole 94-59-7 C10H10O2
thiazine thiazine 11084-06-3 C4H5NS
2-AMINO-4,5-DIHYDRO-1,3-THIAZOL-4-ONE HYDROCHLORIDE 2-AMINO-4,5-DIHYDRO-1,3-THIAZOL-4-ONE HYDROCHLORIDE 2192-06-5 C3H5ClN2OS
Dihydroxydimethyl melamine Dihydroxydimethyl melamine C5H14N6O2
4,7-Dichloroquinoline 4,7-Dichloroquinoline 1138471-54-1 C9H5Cl2N
5-(4-METHOXYPHENYL)-2-THIOPHENECARBOHYDRAZIDE 5-(4-METHOXYPHENYL)-2-THIOPHENECARBOHYDRAZIDE 69202-24-0 C12H12N2O2S
1,3,5-Triazine, 2-phenyl- (9CI) 1,3,5-Triazine, 2-phenyl- (9CI) 1722-18-5 C9H7N3
MORPHOLINE, POLYMER-BOUND MORPHOLINE, POLYMER-BOUND 138048-80-3 C4H9NO
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