106762-04-3Relevant articles and documents
Synthesis of 1-Pyrroline by Denitrogenative Ring Expansion of Cyclobutyl Azides under Thermal Conditions
Ban, Kazuho,Miki, Yuya,Sajiki, Hironao,Sawama, Yoshinari,Tomita, Naohito
, p. 3481 - 3484 (2021/06/17)
We herein report an efficient and systematic synthesis of 1-pyrrolines from cyclobutyl azides under thermal and neutral conditions. The reaction proceeded without any additional reagents, and nitrogen was generated as the sole by-product. Furthermore, the generated 1-pyrrolines could be continuously transformed into pyrroles, N-Boc-amines, and oxaziridines in an one-pot manner. (Figure presented.).
Oligosubstituted pyrroles directly from substituted methyl isocyanides and acetylenes
Lygin, Alexander V.,Larionov, Oleg V.,Korotkov, Vadim S.,De Meijere, Armin
supporting information; experimental part, p. 227 - 236 (2009/06/20)
The formal cycloaddition of α-metallated methyl isocyanides 1 onto the triple bond of electron-deficient acetylenes 2 represents a direct and convenient approach to oligosubstituted pyrroles 3. The scope and limitations of this reaction (24 examples, 2597 % yield) are reported along with an optimization of the reaction conditions and a rationalization of the mechanism. In addition, a related newly developed CuI-mediated synthesis of 2,3-disubstituted pyrroles by the reaction of copper acetylides derived from unactivated terminal alkynes with substituted methyl isocyanides is described (11 examples, 5-88% yield).
Silyl-Substituted Thioimidates as Nitrile Ylide Equivalents
Padwa, Albert,Gasdaska, John R.,Haffmanns, Gunter,Rebello, Hector
, p. 1027 - 1035 (2007/10/02)
Treatment of silyl-substituted thioimidates with silver fluoride in the presence of a trapping agent produces dipolar cycloadducts formally derived from nitrile ylides.The ratio of cycloadducts obtained from the reaction of unsymmetrically substituted dip
