66692-88-4Relevant articles and documents
α-Amino Acid-Isosteric α-Amino Tetrazoles
Zhao, Ting,Kurpiewska, Katarzyna,Kalinowska-T?us?cik, Justyna,Herdtweck, Eberhardt,D?mling, Alexander
supporting information, p. 3009 - 3018 (2016/03/26)
The synthesis of all 20 common natural proteinogenic and 4 otherα-amino acid-isosteric α-amino tetrazoles has been accomplished, whereby the carboxyl group is replaced by the isosteric 5-tetrazolyl group. The short process involves the use of the key Ugi tetrazole reaction followed by deprotection chemistries. The tetrazole group is bioisosteric to the carboxylic acid and is widely used in medicinal chemistry and drug design. Surprisingly, several of the common α-amino acid-isosteric α-amino tetrazoles are unknown up to now. Therefore a rapid synthetic access to this compound class and non-natural derivatives is of high interest to advance the field.
Theoretical study of the cyclization of α-iminothioaldehydes into dihydrothiazoles
Arnaud, Roger,Pelloux-Leon, Nadia,Ripoll, Jean-Louis,Valle, Yannick
, p. 1077 - 1086 (2007/10/02)
When synthesized by retro-Diels-Alder reaction under flash vacuum thermolysis conditions, α-iminothioaldehydes undergo a rearrangement to 2,3-dihydro-1,3-thiazoles.These secondary enamines in turn are transformed into the more stable 2,5-dihydro-1,3-thiazoles upon standing in CDCl3 solution.The route from α-iminothioaldehydes to dihydro-1,3-thiazoles has been studied by ab initio molecular orbital theory.Geometries of stationary points on the potential energy surface were optimized using HF/6-31G(d,p) and MP2/6-31(d,p) calculations.Relative energies wereestimated using MP4STDQ calculations and the 6-31 + G(d,p) basis set and corrected for zero-point vibrational energies.Intrinsic reaction coordinate calculations at HF/6-31G(d,p) level were performed in order to check the profile of the proposed rearrangement.These calculations support the experimental findings.The most energy requiring step was found to be trans -> cis isomerization of the methylimino group -1 at the QCISD(T)/6-31 + G(d,p) level>
NEW REACTIONS WITH THIOALDEHYDES AND THIENIUM CATIONS
Arnaud, Roger,Chavant, Pierre-Yves,Hagoug, Fatiha,Pelloux-Leon, Nadia,Ripoll, Jean-Louis,Vallee, Yannick
, p. 319 - 320 (2007/10/02)
i) When generated under FVT conditions α-imino-thioaldehydes undergo a cyclization to dihydro-1,3-thiazoles. ii) Thienium cations, generated during a Pummerer reaction, can be trapped with dienes.