41470-93-3Relevant articles and documents
Guanidinum chloride as dehydrocyclization agent in the synthesis of 2-fuctionalized (4H)-3,1-benzoxazine-4-ones
Nikpour, Farzad,Bahmani, Asrin,Havasi, Forugh,Sharafi-Kolkeshvandi, Mahnaz
, p. 34 - 37 (2014/02/14)
A facile and expedient route for the synthesis of 2-ethoxy- and 2-(ethylcarboxylate)-(4H)-3,1-benzoxazine-4-ones is described using guanidinium chloride as a safe and convenient dehydrocyclization agent. High yields of the products obtain under mild react
Ester vs. amide on folding: A case study with a 2-residue synthetic peptide
Vijayadas, Kuruppanthara N.,Nair, Roshna V.,Gawade, Rupesh L.,Kotmale, Amol S.,Prabhakaran, Panchami,Gonnade, Rajesh G.,Puranik, Vedavadi G.,Rajamohanan, Pattuparambil R.,Sanjayan, Gangadhar J.
, p. 8348 - 8356 (2013/12/04)
Although known for their inferiority as hydrogen-bonding acceptors when compared to amides, esters are often found at the C-terminus of peptides and synthetic oligomers (foldamers), presumably due to the synthetic readiness with which they are obtained using protected peptide coupling, deploying amino acid esters at the C-terminus. When the H-bonding interactions deviate from regularity at the termini, peptide chains tend to "fray apart". However, the individual contributions of C-terminal esters in causing peptide chain end-fraying goes often unnoticed, particularly due to diverse competing effects emanating from large peptide chains. Herein, we describe a striking case of a comparison of the individual contributions of C-terminal ester vs. amide carbonyl as a H-bonding acceptor in the folding of a peptide. A simple two-residue peptide fold has been used as a testing case to demonstrate that amide carbonyl is far superior to ester carbonyl in promoting peptide folding, alienating end-fraying. This finding would have a bearing on the fundamental understanding of the individual contributions of stabilizing/destabilizing non-covalent interactions in peptide folding.
A simple and expedient method for the stepwise synthesis of 2-ethoxy-(4H)-3,1-benzoxazine-4-ones
Bahmani, Asrin,Sharafi-Kolkeshvandi, Mahnaz,Nikpour, Farzad
experimental part, p. 434 - 437 (2012/05/20)
A simple and practical route is described for the synthesis of 2-ethoxy-(4H)-3,1-benzoxazine-4-ones using the coupling reaction of anthranilic acid derivatives with diethyl dicarbonate following with fast cyclization of the carbamate adduct with a dehydro
