70008-81-0Relevant articles and documents
Trisulfur-Radical-Anion-Triggered C(sp2)-H Amination of Electron-Deficient Alkenes
Nguyen, Khang X.,Nguyen, Thao T.,Nguyen, Tung T.,Pham, Hoai T. B.,Pham, Phuc H.,Phan, Nam T. S.,Wang, Haobin,Yang, Chou-Hsun
supporting information, p. 9751 - 9756 (2020/12/21)
A trisulfur-radical-anion (S3˙-)-triggered C(sp2)-H amination of α,β-unsaturated carbonyl derivatives with simple amines has been demonstrated. This protocol provides convenient access to a variety of synthetically valuable N-unprotected and secondary β-enaminones with absolute Z selectivity and tertiary β-enaminones with E selectivity. Mechanistic probe and electronic structure theory calculations suggest that S3˙- initiates the nucleophilic attacks via a thiirane intermediate.
Reaction of arynes with vinylogous amides: Nucleophilic addition to the ortho-quinodimethide intermediate
Li, Ran,Wang, Xuemei,Wei, Zhibin,Wu, Chunrui,Shi, Feng
supporting information, p. 4366 - 4369 (2013/09/24)
The reaction of arynes with vinylogous amides containing no free N-H bonds proceeds in a [2 + 2] cycloaddition fashion at ambient temperature. The electronic properties of the vinylogous amides allow for the cycloadducts undergoing a facile ring-opening p
Straightforward Novel One-Pot Enaminone and Pyrimidine Syntheses by Coupling-Addition-Cyclocondensation Sequences
Karpov, Alexei S.,Mueller, Thomas J. J.
, p. 2815 - 2826 (2007/10/03)
The coupling of acid chlorides 1 with terminal alkynes 2 using only one equivalent (!) of triethylamine under Sonogashira conditions followed by subsequent addition of primary or secondary amines 4 to the intermediate alkynones 3 represents a straight-for
A novel synthesis of α- and β-morpholino enones by electron transfer sensitized photooxidation of 2-morpholinocyclopropanols
Weigel, Wilfried,Henning, Hans-Georg
, p. 1893 - 1894 (2007/10/03)
An electron transfer mechanism is proposed to account for the photooxidation of 2-morpholinocyclopropanols 1 to the amino enone derivatives 2 and 3 in the presence of 9,10-dicyanoanthracene or triphenylpyrylium tetrafluoroborate and triplet oxygen.
The influence of substituents on the photochemical generation and stability of 2-morpholinocyclopropanols
Weigel,Schiller,Reck,Henning
, p. 6737 - 6740 (2007/10/02)
By irradiation in oxygen-free ether α- or β-substituted β-morpholinopropiophenones 1a-c form the corresponding cyclopropanols 2 with 1-aryl and 2-morpholino group in a relative cis-configuration in high yields. The photocyclization of pure 1a-c enantiomer
STUDY OF THE ESCHENMOSER SULFIDE CONTRACTION METHOD WITH AND WITHOUT A THIOPHILE
Corsaro, A.,Perrini, G.,Testa, M. G.,Chiacchio, U.
, p. 197 - 206 (2007/10/02)
Results obtained and observations made by applying the title method for the synthesis of enaminones 5a-o, using triphenylphosphine as a thiophile and triethylamine as a base, are reported.The product distributions of the deprotonations of α-phenacylthio iminium bromides with and without thiophile and those known from thiouronium and heterocyclic thionium analogs are compared.Key words: Enaminones; α-phenacylthio iminium bromides; disulfides; thiiranes.
KINETIC RELATIONSHIPS OF THE REACTION OF 1,3-DIARYL-1-PROPYN-3-ONES WITH MORPHOLINE AND BUTYLAMINE IN POLAR APROTIC SOLVENTS
Korshunov, S. P.,Slyusareva, O. M.,Korzhova, N. V.,Kazantseva, V. M.
, p. 815 - 819 (2007/10/02)
The kinetics of the reaction of substituted 1,3-diphenyl-1-propyn-3-ones with butylamine and morpholine in acetonitrile and DMFA were studied by a polarographic method in the range of 294-323 deg K with the amines at concentrations (0.05-0.1 mol) securing nondependance of the second-order rate constants on the concentration of the amine.The reactions in acetonitrile and DMFA are characterized by lower ΔH(activ.) values and more negative ΔS(activ.) values than the reactions in alcohol.This is due to the larger degree of separation of the charges and to the solvationstate in the aprotic solvents.It is confirmed by data on the effect of the substituents in the substituted ketones on the rate of their reaction with the amines.
TRISUBSTITUTED THIAZOLES BY A 6?-ELECTROCYCLIZATION OF IMINOTHIOCARBONYL YLIDES
Corsaro, A.,Tarantello, M.,Purrello, G.
, p. 3305 - 3308 (2007/10/02)
Iminothiocarbonyl ylides are generated by a sulfur ligand exchange reaction of sulfonium salts and undergo a 6?-electrocyclic closure and aromatization to tri substituted thiazoles.Related carbonyl ylides preferred a 4?-electrocyclization.
