87451-35-2Relevant academic research and scientific papers
Mercuric Acetate Cyclization of 4-(Pyrrolylmethyl)- and 4-(Indolylmethyl)piperidines to Bridged Polycyclic Systems
Bosch, Joan,Mauleon, David,Feliz, Miguel,Granados, Ricardo
, p. 4836 - 4841 (1983)
The mercuric acetate cyclization of 4-(pyrrolylmethyl)piperidines 4 and 9 as well as of 4-(indolylmethyl)piperidines 13 and 18 to the corresponding bridged polycyclic systems is studied.When the reaction was carried out in aqueous AcOH solution, mixtures of the starting piperidine and the corresponding cyclized product were obtained.The recovery of piperidine is attributed to the mercuration of the heteroatomic ring, which prevents the cyclization of the intermediate iminium salt.In the pyrrole series, the use of EDTA in alkaline medium avoids mercuration and gives rise exclusively to the cyclized products 5 and 10 in high yields.However, these alkaline conditions are not appropriate for cyclization of (indolylmethyl)piperidines, because of the formation of the corresponding 2-piperidinones 15 and 20 as the major products.The best yield of methanoazociniondole 14 was obtaind when the oxidative cyclization of 13 was effected in the presence of EDTA at pH 6-7, whereas methanodiazocinoindole 19 was more conveniently prepared in aqueous EDTA solution.
Synthesis of N-alkyl pyrroles via decarboxylation/dehydration in neutral ionic liquid under catalyst-free conditions
Yadav, Veena D.,Dighe, Shashikant U.,Batra, Sanjay
, p. 57587 - 57590 (2015/01/08)
A general route to N-alkyl pyrroles by reacting aromatic, heteroaromatic or aliphatic aldehydes with 4-hydroxyproline in ionic liquid under neutral condition was developed. The ionic liquid can be readily recovered and reused for up to 5 reaction cycles without any effect on the yield of the product formed. The utility of the protocol for the one-pot synthesis of 9H-benzo[e]pyrrolo[2,1-b][1,3]oxazines is also presented.
An elegant protocol for the synthesis of N-substituted pyrroles through C-N cross coupling/aromatization process using CuFe2O4 nanoparticles as catalyst under ligand-free conditions
Satish,Reddy, K. Harsha Vardhan,Ramesh,Kumar, B.S.P. Anil,Nageswar
supporting information, p. 2596 - 2599 (2014/05/06)
A simple and efficient, ligand-free C-N cross-coupling of aryl halides/benzyl bromides with trans-4-hydroxy-l-proline has been developed to produce aromatized N-substituted pyrroles, using a catalytic amount of magnetically separable and recyclable CuFe2O4 nanoparticles, in the presence of Cs2CO3 in DMSO at 100 °C.
Trans-4-Hydroxy-l-proline: A novel starting material for N-alkylpyrroles synthesis
Vijay Kumar,Rama Rao
experimental part, p. 3237 - 3239 (2011/06/28)
The reaction of aldehydes with trans-4-hydroxy-l-proline was studied for the first time, resulting in the formation of N-alkylpyrroles in good to excellent yields, via decarboxylation followed by redox isomerization under neutral conditions. The neutral c
O-Iodoxybenzoic acid (IBX): A versatile reagent for the synthesis of N-substituted pyrroles mediated by β-cyclodextrin in water
Narayana Murthy,Nageswar
supporting information; experimental part, p. 4481 - 4484 (2011/09/19)
O-Iodoxybenzoic acid (IBX), a very mild and efficient hypervalent iodine(V) reagent, aromatizes diversely substituted 1-benzylpyrrolidines and N-substituted l-proline analogues to the corresponding substituted pyrroles in good to excellent yields under mild conditions mediated by β-cyclodextrin in water at room temperature. To the best of our knowledge, this is the first report on IBX, promoting complete aromatization leading to N-benzylpyrroles from the corresponding saturated five membered heterocyclic derivatives in water medium.
