87451-35-2Relevant articles and documents
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.
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
