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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-Ethyl-5-methyl-d8)-pyridine-4-boronic acid (2-Ethyl-5-methyl-d8)-pyridine-4-boronic acid 2225178-44-7 C8H12BNO2
(2-Methyl-6-piperidino-d13)-pyridine-4-boronic acid (2-Methyl-6-piperidino-d13)-pyridine-4-boronic acid 2225170-69-2 C11H17BN2O2
[2-(n-Propyl)-5-methyl-d10]-pyridine-4-boronic acid [2-(n-Propyl)-5-methyl-d10]-pyridine-4-boronic acid 2225176-93-0 C9H14BNO2
[4-Methyl-5-(n-propyl)-d10]-pyridine-3-boronic acid [4-Methyl-5-(n-propyl)-d10]-pyridine-3-boronic acid 2225173-91-9 C9H14BNO2
[4-Methyl-6-(n-propyl)-d10]-pyridine-3-boronic acid [4-Methyl-6-(n-propyl)-d10]-pyridine-3-boronic acid 2225170-73-8 C9H14BNO2
[6-Methyl-5-(sec-butyl)-d12]-pyridine-3-boronic acid [6-Methyl-5-(sec-butyl)-d12]-pyridine-3-boronic acid 2225153-36-4 C10H16BNO2
2-(iso-Propoxy-d7)-6-trifluoromethylpyridine-4-boronic acid 2-(iso-Propoxy-d7)-6-trifluoromethylpyridine-4-boronic acid 2225176-09-8 C9H4BD7F3NO3
2-(Methylamino-d3)-pyridine 2-(Methylamino-d3)-pyridine 1185313-37-4 C6H8N2
2-(Methylethylaminopyridine-d11)-4-boronic acid 2-(Methylethylaminopyridine-d11)-4-boronic acid 2225179-21-3 C8H13BN2O2
2-(tert-Butoxy-d9)-6-trifluoromethylpyridine-4-boronic acid 2-(tert-Butoxy-d9)-6-trifluoromethylpyridine-4-boronic acid 2225174-92-3 C10H13BF3NO3
2,6-Dibromopyridine-d3 2,6-Dibromopyridine-d3 1185318-80-2 C5Br2D3N
2-Acetyl-6-(methyl-d3)-pyridine 2-Acetyl-6-(methyl-d3)-pyridine 1185320-03-9 C8H9NO
2-Amino-4-(ethyl-d5)-pyridine 2-Amino-4-(ethyl-d5)-pyridine 1185319-94-1 C7H10N2
2-Amino-4-(n-propoxy-d7)-pyridine 2-Amino-4-(n-propoxy-d7)-pyridine 1643564-67-3 C8H12N2O
2-Amino-4-(piperidinopyridine-d13) 2-Amino-4-(piperidinopyridine-d13) 1643544-19-7 C10H15N3
2-Amino-5-(ethylpyridine-d8) 2-Amino-5-(ethylpyridine-d8) 1643564-38-8 C7H10N2
2-Bromo(pyridine-d3)-4-boronic acid pinacol ester 2-Bromo(pyridine-d3)-4-boronic acid pinacol ester 2368221-46-7 C11H17BBrD3NO3
2-Bromo-4-(iso-propyl)pyridine-d10 2-Bromo-4-(iso-propyl)pyridine-d10 1643575-94-3 C8H10BrN
2-Bromo-4-(sec-butyl-d9)-pyridine 2-Bromo-4-(sec-butyl-d9)-pyridine 1643537-84-1 C9H12BrN
2-Bromo-4-piperidinopyridine-d13 2-Bromo-4-piperidinopyridine-d13 1643575-88-5 C10H13BrN2
2-Bromo-5-(iso-butyl-d9)-pyridine 2-Bromo-5-(iso-butyl-d9)-pyridine 1643542-32-8 C9H12BrN
2-Bromo-5-(tert-butyl)pyridine-d12 2-Bromo-5-(tert-butyl)pyridine-d12 1643562-91-7 C9H12BrN
2-Bromo-6-(ethyl-d5)-pyridine 2-Bromo-6-(ethyl-d5)-pyridine 1185313-44-3 C7H8BrN
2-Bromo-6-(tert-butoxy-d9)-pyridine 2-Bromo-6-(tert-butoxy-d9)-pyridine 1185314-70-8 C9H12BrNO
2-Chloro-3-cyano-6-(ethyl-d5)-pyridine 2-Chloro-3-cyano-6-(ethyl-d5)-pyridine 1185314-72-0 C8H2ClD5N2
2-Chloro-3-trifluoromethyl-6-(iso-propyl-d7)-pyridine 2-Chloro-3-trifluoromethyl-6-(iso-propyl-d7)-pyridine 1185316-54-4 C9H2ClD7F3N
2-Chloro-5-(acetyl-d3)-pyridine 2-Chloro-5-(acetyl-d3)-pyridine 1185314-86-6 C7H6ClNO
2-Cyano-6-(iso-butyl-d9)-pyridine-4-boronic acid 2-Cyano-6-(iso-butyl-d9)-pyridine-4-boronic acid 2225174-89-8 C10H13BN2O2
2-Fluoro-6-(n-propyl-d7)-pyridine-4-boronic acid 2-Fluoro-6-(n-propyl-d7)-pyridine-4-boronic acid 2225169-56-0 C8H11BFNO2
3,6-Dibromopyridazine-d2 3,6-Dibromopyridazine-d2 1643543-37-6 C4H2Br2N2
3-Amino-6-(dimethylamino-d6)-pyridazine 3-Amino-6-(dimethylamino-d6)-pyridazine 1643538-11-7 C6H4D6N4
3-Amino-6-(iso-butyl-d9)-pyridine 3-Amino-6-(iso-butyl-d9)-pyridine 1643542-41-9 C9H14N2
3-Amino-6-(tert-butoxy-d9)-pyridazine 3-Amino-6-(tert-butoxy-d9)-pyridazine 1643542-08-8 C8H4D9N3O
3-Bromo-(5-methyl-6-methoxy-d6)-pyridine 3-Bromo-(5-methyl-6-methoxy-d6)-pyridine 1643538-41-3 C7H8BrNO
3-Bromo-[2-methyl-5-(iso-propyl)-d10]-pyridine 3-Bromo-[2-methyl-5-(iso-propyl)-d10]-pyridine 1643538-33-3 C9H12BrN
3-Bromo-[4-methyl-6-(iso-butyl)-d12]-pyridine 3-Bromo-[4-methyl-6-(iso-butyl)-d12]-pyridine 1643562-75-7 C10H14BrN
3-Bromo-[5-(n-propyl)-6-methoxy-d10]-pyridine 3-Bromo-[5-(n-propyl)-6-methoxy-d10]-pyridine 1643538-80-0 C9H12BrNO
3-Bromo-5-(diethylamino-d10)-pyridine 3-Bromo-5-(diethylamino-d10)-pyridine 1643537-70-5 C9H13BrN2
3-Bromo-5-(iso-butyl-d9)-pyridine 3-Bromo-5-(iso-butyl-d9)-pyridine 1643562-98-4 C9H12BrN
3-Bromo-5-(N-methylpiperazin-1-yl)pyridine-d14 3-Bromo-5-(N-methylpiperazin-1-yl)pyridine-d14 1643562-63-3 C10H14BrN3
3-Bromo-5-(piperidino)pyridine-d13 3-Bromo-5-(piperidino)pyridine-d13 1643576-13-9 C10H13BrN2
3-Bromo-5-cyanopyridine-d3 3-Bromo-5-cyanopyridine-d3 1643576-67-3 C6H3BrN2
3-Bromo-5-fluoropyridine-d3 3-Bromo-5-fluoropyridine-d3 1643564-95-7 C5H3BrFN
3-Bromo-6-(ethoxy)pyridine-d8 3-Bromo-6-(ethoxy)pyridine-d8 1643576-97-9 C7H8BrNO
3-Bromo-6-(iso-butyl)pyridazine-d11 3-Bromo-6-(iso-butyl)pyridazine-d11 1643539-46-1 C8BrD11N2
3-Bromo-6-(methylamino-d3)-pyridine 3-Bromo-6-(methylamino-d3)-pyridine 1185306-63-1 C6H7BrN2
3-Bromo-6-(morpholino)pyridazine-d10 3-Bromo-6-(morpholino)pyridazine-d10 1643579-72-9 C8BrD10N3O
3-Bromo-6-(piperidino-d10)-pyridine 3-Bromo-6-(piperidino-d10)-pyridine 1643576-93-5 C10H13BrN2
3-Bromo-6-(sec-butyl)pyridazine-d11 3-Bromo-6-(sec-butyl)pyridazine-d11 1643576-84-4 C8H11BrN2
3-Bromo-6-ethoxypyridazine-d7 3-Bromo-6-ethoxypyridazine-d7 1643564-22-0 C6H7BrN2O
3-Bromo-6-methylpyridine-d6 3-Bromo-6-methylpyridine-d6 1643575-74-9 C6H6BrN
3-Chloro-6-(iso-propoxy-d7)pyridine 3-Chloro-6-(iso-propoxy-d7)pyridine 1185315-84-7 C8H10ClNO
3-Hydroxy-6-(ethyl-d5)-pyridine 3-Hydroxy-6-(ethyl-d5)-pyridine 1185315-69-8 C7H9NO
4-(iso-Propyl-d7)-pyridine-2-boronic acid pinacol ester 4-(iso-Propyl-d7)-pyridine-2-boronic acid pinacol ester 2223045-16-5 C14H22BNO2
3-Chloro-2-(trifluoromethyl)-pyridine 3-Chloro-2-(trifluoromethyl)-pyridine 749875-32-9 C6H3ClF3N
Spiro[cyclohexane-1,3'(1'H)-furo[3,4-c]pyridine]-1',4-dione Spiro[cyclohexane-1,3'(1'H)-furo[3,4-c]pyridine]-1',4-dione 328233-20-1 C12H11NO3
5-(BROMOMETHYL)-3-METHYLISOXAZOLE 5-(BROMOMETHYL)-3-METHYLISOXAZOLE 36958-61-9 C5H6BrNO
4-(CHLOROMETHYL)-2-(2-FURYL)-1,3-THIAZOLE 4-(CHLOROMETHYL)-2-(2-FURYL)-1,3-THIAZOLE 13386-49-7 C8H6ClNOS
4-BROMO-6-CHLORO-1H-INDAZOLE 4-BROMO-6-CHLORO-1H-INDAZOLE 885519-03-9 C7H4BrClN2
6-(PIPERIDIN-1-YL)PYRIDINE-2-BORONIC ACID PINACOL ESTER 6-(PIPERIDIN-1-YL)PYRIDINE-2-BORONIC ACID PINACOL ESTER 1315350-93-6 C16H25BN2O2
4-CHLORO-2-(4-FLUOROPHENYL)PYRIMIDINE 4-CHLORO-2-(4-FLUOROPHENYL)PYRIMIDINE 76128-71-7 C10H6ClFN2
4-(n-Propyl-d7)-pyridine-2-boronic acid pinacol ester 4-(n-Propyl-d7)-pyridine-2-boronic acid pinacol ester 2223035-45-6 C14H17BD7NO3
4-(Pyrrolidinopyridine-d11)-2-boronic acid pinacol ester 4-(Pyrrolidinopyridine-d11)-2-boronic acid pinacol ester 2223030-27-9 C15H23BN2O2
4-[(iso-Propoxy)pyridine-d10]-2-boronic acid pinacol ester 4-[(iso-Propoxy)pyridine-d10]-2-boronic acid pinacol ester 2223055-90-9 C14H22BNO3
4-[(n-Propyl)pyridine-d10]-2-boronic acid pinacol ester 4-[(n-Propyl)pyridine-d10]-2-boronic acid pinacol ester 2223046-53-3 C14H22BNO2
4-Amino(pyrimidine-2-d1) 4-Amino(pyrimidine-2-d1) 1185312-00-8 C4H5N3
4-Amino-2-bromopyridine-3,5,6-d3 4-Amino-2-bromopyridine-3,5,6-d3 1643543-41-2 C5H5BrN2
4-Bromo-(2,3-dimethyl-d6)-pyridine 4-Bromo-(2,3-dimethyl-d6)-pyridine 1643544-22-2 C7H2BrD6N
4-Bromo-(3,6-dimethyl-d6)-pyridine 4-Bromo-(3,6-dimethyl-d6)-pyridine 1643541-84-7 C7H8BrN
4-Bromo-[2-(tert-butyl)-3-methyl-d12]-pyridine 4-Bromo-[2-(tert-butyl)-3-methyl-d12]-pyridine 1643542-88-4 C10H14BrN
4-Bromo-2-(iso-propoxy-d7)-pyrimidine 4-Bromo-2-(iso-propoxy-d7)-pyrimidine 1185316-23-7 C7H9BrN2O
4-Bromo-2-(methyl-d3)-pyrimidine 4-Bromo-2-(methyl-d3)-pyrimidine 1185316-25-9 C5H5BrN2
4-Bromo-2-(morpholino-d8)-pyridine 4-Bromo-2-(morpholino-d8)-pyridine 1643576-51-5 C9H11BrN2O
4-Bromo-2-(pyrrolidino)pyridine-d11 4-Bromo-2-(pyrrolidino)pyridine-d11 1643575-71-6 C9H11BrN2
4-Bromo-2-(tert-butyl)pyridine-d12 4-Bromo-2-(tert-butyl)pyridine-d12 1643579-74-1 C9H12BrN
4-Bromo-2-cyano-6-(iso-butyl-d9)-pyridine 4-Bromo-2-cyano-6-(iso-butyl-d9)-pyridine 1643542-77-1 C10H11BrN2
4-Bromo-2-cyanopyridine-d3 4-Bromo-2-cyanopyridine-d3 1643562-70-2 C6H3BrN2
4-Bromo-2-methylethylaminopyridine-d11 4-Bromo-2-methylethylaminopyridine-d11 1643544-13-1 C8H11BrN2
4-Bromo-2-trifluoromethyl-6-(methoxy-d3)-pyridine 4-Bromo-2-trifluoromethyl-6-(methoxy-d3)-pyridine 1643542-67-9 C7H2BrD3F3NO
4-Chloro-5-methyl-2-(ethoxy-d5)-pyrimidine 4-Chloro-5-methyl-2-(ethoxy-d5)-pyrimidine 1185306-79-9 C7H9ClN2O
4-Chloro-5-methyl-2-(methyl-d3)-pyrimidine 4-Chloro-5-methyl-2-(methyl-d3)-pyrimidine 1185306-85-7 C6H7ClN2
4-Chloro-6-amino-2-(n-propyl-d7)-pyrimidine 4-Chloro-6-amino-2-(n-propyl-d7)-pyrimidine 1185316-84-0 C7H10ClN3
4-Chloro-6-methyl-2-(methoxy-d3)-pyrimidine 4-Chloro-6-methyl-2-(methoxy-d3)-pyrimidine 1185309-19-6 C6H7ClN2O
5-(Diethylamino-d10)-pyridine-2-boronic acid pinacol ester 5-(Diethylamino-d10)-pyridine-2-boronic acid pinacol ester 2223055-43-2 C15H25BN2O2
5-(tert-Butyl-d9)-pyridine-2-boronic acid pinacol ester 5-(tert-Butyl-d9)-pyridine-2-boronic acid pinacol ester 2223052-67-1 C15H24BNO2
5-[(n-Propoxy)pyridine-d10]-2-boronic acid pinacol ester 5-[(n-Propoxy)pyridine-d10]-2-boronic acid pinacol ester 2223040-20-6 C14H22BNO3
5-[(tert-Butoxy)pyridine-d12]-3-boronic acid pinacol ester 5-[(tert-Butoxy)pyridine-d12]-3-boronic acid pinacol ester 2223039-35-6 C15H24BNO3
5-Bromo-2-(methoxy-d3)-pyrimidine 5-Bromo-2-(methoxy-d3)-pyrimidine 1185315-62-1 C5H2BrD3N2O
5-Bromo-2-(piperidino-d10)-pyrimidine 5-Bromo-2-(piperidino-d10)-pyrimidine 1643539-13-2 C9H12BrN3
5-Bromo-2-chloro-4-(methyl-d3)-pyrimidine 5-Bromo-2-chloro-4-(methyl-d3)-pyrimidine 1643564-45-7 C5H4BrClN2
5-Bromo-4-(iso-butyl-d9)-pyrimidine 5-Bromo-4-(iso-butyl-d9)-pyrimidine 1643538-84-4 C8H11BrN2
5-Bromo-4-chloro-2-(n-propyl-d7)-pyrimidine 5-Bromo-4-chloro-2-(n-propyl-d7)-pyrimidine 1643542-24-8 C7HBrClD7N2
5-Bromopyrimidine-2-d1 5-Bromopyrimidine-2-d1 1185309-28-7 C4H3BrN2
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
2-(1,1,2,3,3,3-HEXAFLUOROPROPYL)TETRAHYDROFURAN 2-(1,1,2,3,3,3-HEXAFLUOROPROPYL)TETRAHYDROFURAN 53005-42-8 C7H8F6O
BOC-D-NVA-OSU BOC-D-NVA-OSU 213178-93-9 C14H22N2O6
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