28416-91-3Relevant articles and documents
3,3-dichloro-1,2-diphenylcyclopropene (CPICL)-mediated synthesis of n α-protected amino acid azides and α-ureidopeptides
Panguluri, Nageswara Rao,Samarasimhareddy,Madhu,Sureshbabu, Vommina V.
, p. 1001 - 1005 (2014/05/06)
Rapid synthesis of acid azides via in situ generation of acid chlorides using CPICl as chlorinating agent from the corresponding Nα- protected amino acids is described. Also the conversion of acid azides into ureidopeptides through the Curtius rearrangement under ultrasonication is delineated. The mildness of the protocol renders the acid-sensitive substrates to afford the corresponding amino acid azides and ureidopeptides in good yields. Diphenylcyclopropenone has also been recovered from the reaction mixture and reused. Georg Thieme Verlag Stuttgart New York.
Application of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) for the synthesis of acid azides
Naik, Shankar A.,Lalithamba,Sureshbabu, Vommina V.
experimental part, p. 103 - 109 (2011/04/15)
Conversion of acids to acyl azides using peptide coupling agent TBTU has been demonstrated. The procedure is simple and applicable to a range of carboxylic acids under mild reaction conditions. The protocol is extended to the synthesis of urethane protect
Facile one step synthesis of acyl azides and Nα-Fmoc/Boc/Z protected amino acid azides employing benzotriazole-1-yl-oxy-tris- (dimethylamino)-phosphonium hexafluorophosphate (BOP)
Vasantha,Sureshbabu, Vommina V.
experimental part, p. 812 - 817 (2011/01/04)
A simple route for the preparation of acyl azides from the corresponding carboxylic acids employing the peptide-coupling agent BOP is described. The procedure is simple, clean and high yielding. The chemistry is also extended to the preparation of several urethane protected amino acid azides (eight examples) as well.
New and simple synthesis of acid azides, ureas and carbamates from carboxylic acids: Application of peptide coupling agents EDC and HBTU
Sureshbabu, Vommina V.,Lalithamba,Narendra,Hemantha
experimental part, p. 835 - 840 (2010/06/20)
Conversion of carboxylic acids into acid azides using peptide coupling agents, EDC and HBTU is described. The procedure is efficient, practical and applicable to a diverse range of carboxylic acids including N-protected amino acids. Using the same reagents, one-pot synthesis of ureas, dipeptidyl urea esters and carbamates from acids has also been achieved. The Royal Society of Chemistry 2010.
Some Applications of the Curtius Rearrangement
Moutevelis-Minakakis, Panagiota,Photaki, Iphigenia
, p. 2277 - 2282 (2007/10/02)
Pairs of optically pure enantiomers of substituted 1,1-diamines have been prepared from the azides of L-amino-acids via the Curtius rearrangement.This synthesis is based on the interchange of two groups attached to the asymmetrically substituted tetrahedr
MACROHETEROCYCLES. XVII. SYNTHESIS AND ENANTIOSELECTIVE CHARACTERISTICS OF CHIRAL N,N'-DIACYLDIAZA-18-CROWN-ETHERS
Luk'yanenko, N. G.,Bogat-skii, A. V.,Basok, S. S.,Ostrovskaya, L. K.,Nazarova, N. Yu.,Karpenko, L. P.
, p. 1438 - 1444 (2007/10/02)
N,N'-Diacyldiaza-18-crown-6 ethers were obtained by the acylation of diaza-18-crown-6 with amino acids.The enantioselectivity coefficients were determined for the chiral compound in relation to the L and D isomers of valine.The obtained compounds represent a promising class of enantioselective complexones.
Amino Acids and Peptides. VI. Curtius Rearrangement of Acyl Amino Acid and Peptide Azides and Reactivity of the Isocyanates
Okada, Yoshio,Tsuda, Yuko,Yagyu, Masami
, p. 2254 - 2258 (2007/10/02)
Studies on the rate of Curtius rearrangement of acyl amino acid and peptide azides were carried out by means of IR (infrared) spectrophotometry at 25 deg.It was found that Z-Gly-N3 and Z-Pro-N3 were more stable than the other acyl amino acid azides.The re
