127572-58-1Relevant academic research and scientific papers
One-pot synthesis of pyrroles using a titanium-catalyzed multicomponent coupling procedure
Pasko, Cody M.,Dissanayake, Amila A.,Billow, Brennan S.,Odom, Aaron L.
, p. 1168 - 1176 (2016/02/16)
A simple one-pot procedure for the production of 2-carboxylpyrroles with 4-alkyl, 5-alkyl, 4-aryl, 4-aryl-5-alkyl, or 3,4-diaryl substitution patterns is presented. The procedure involves the titanium-catalyzed multicomponent coupling of alkynes, primary amines and isonitriles to give 1,3-diimines in situ; the multicomponent product is then treated with the ethyl ester of glycine hydrochloride to give the NH-pyrrole. The reaction can be carried out with the neutralized glycine ester or with the hydrochloride salt using DBU as a base. Yields of pyrrole based on starting alkyne varied from 25 to 65% over the one pot procedure, and in most cases only one regioisomer of the product is observed. Further, it is proposed that the regioselectivities of the reactions are a result of rate-determining ring closure after relatively fast transimination with glycine ethyl ester.
Nano-copper catalysed highly regioselective synthesis of 2,4-disubstituted pyrroles from terminal alkynes and isocyanides
Tiwari, Dipak Kumar,Pogula, Jaya,Sridhar,Tiwari, Dharmendra Kumar,Likhar, Pravin R.
, p. 13646 - 13649 (2015/09/02)
Nano-copper(0) stabilized on alumina prepared from Cu-Al hydrotalcite has been reported for completely regioselective synthesis of 2,4-disubstituted pyrroles from unactivated terminal aromatic/aliphatic alkynes and isocyanides. The reaction is operational
An unusual dehalogenation in the Suzuki coupling of 4-bromopyrrole-2-carboxylates
Handy, Scott T.,Bregman, Howard,Lewis, Jennifer,Zhang, Xiaolei,Zhang, Yanan
, p. 427 - 430 (2007/10/03)
An unusual dehalogenation of 4-bromopyrrole-2-carboxylates under Suzuki coupling conditions has been observed. This dehalogenation can be suppressed by protection of the pyrrole nitrogen. Using a BOC protecting group, not only is dehalogenation suppressed
The Preparation of Pyrrole-2-carboxylates from Vinyl Sulfones
Arnold, Dennis P.,Burgess-Dean, Leon,Hubbard, Jason,Rahman, M. Abdur
, p. 969 - 974 (2007/10/02)
The reaction of the anion of ethyl isocyanoacetate with suitably substituted vinyl p-tolyl sulfones gives fair to good yields of pyrrole-2-carboxylates substituted in the 3-, 4- or 3- and 4-positions.From the reaction of 1-phenyl-1-tolylsulfonylethene with ethyl isocyanoacetate, two diastereoisomers of ethyl 4,6-diphenyl-4,6-bis(p-tolylsulfonyl)-3,4,5,6-tetrahydro-2H-azepine-2-carboxylate (4) were also isolated.
Application of 2-Substituted Vinamidinium Salts to the Synthesis of 2,4-Disubstituted Pyrroles
Gupton, John T.,Krolikowski, Dale A.,Yu, Richard H.,Riesinger, Steve W.,Sikorski, James A.
, p. 4735 - 4740 (2007/10/02)
A variety of 2-substituted vinamidinium salts react with α-amino acid esters under basic conditions to produce 2-carbethoxy-4-substituted-pyrroles in good yield.The overall process represents a short and efficient synthesis of highly functionalized pyrrol
