118429-46-2Relevant academic research and scientific papers
One-Pot Double-Annulation Strategy for the Synthesis of Unusual Fused Bis-Heterocycles
Abdul-Rashed, Shukree,Alachouzos, Georgios,Brennessel, William W.,Frontier, Alison J.
supporting information, p. 4350 - 4354 (2020/06/04)
A novel metal-free double-annulation cascade for the construction of unusual fused heterocyclic systems is described. This simple protocol enables the sequential assembly of two rings in one pot from two simple precursors. Acidic conditions promote the condensation and the intramolecular alkynyl Prins reaction of an enyne or arenyne alcohol with a cyclic hemiaminal to form a five-, six-, or seven-membered oxacycle followed by a seven-or eight-membered azacycle. In this transformation, chemical complexity is rapidly generated with the formation of three new bonds (one C-O, one C-C, and one C-N) in one synthetic operation. The strategy is modular and relatively general, providing access to a series of unique fused bicyclic scaffolds.
Iridium-Catalyzed Intramolecular Oxidative Cyclization of Alkenyl Amides and Alkenoic Acids
Nagamoto, Midori,Nishimura, Takahiro,Yorimitsu, Hideki
, p. 4272 - 4282 (2017/09/13)
An iridium/dppf complex efficiently catalyzed the oxidative cyclization of N sulfonyl alkenyl amides and alkenoic acids. Electron deficiena?t alkenes were effective as sacrificial hydrogen acceptors. High selectivity of the oxidative cyclization over the
Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides
Paz, Nieves R.,Rodríguez-Sosa, Dionisio,Valdés, Haydee,Marticorena, Ricardo,Melián, Daniel,Copano, M. Belén,González, Concepción C.,Herrera, Antonio J.
, p. 2370 - 2373 (2015/06/02)
Mechanistic evidence observed in Hofmann-L?ffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity. (Chemical Equation Presented).
Remote chiral induction in vinyl sulfonium salt-mediated ring expansion of hemiaminals into epoxide-fused azepines
Yar, Muhammad,Unthank, Matthew G.,McGarrigle, Eoghan M.,Aggarwal, Varinder K.
supporting information; experimental part, p. 372 - 375 (2011/10/09)
The planet of the azepines: Epoxy-fused azepines have been synthesized in a highly selective reaction with hemiaminals and vinyl sulfonium salts. Stereochemistry is controlled by the substituent at the four- or five-position of the hemiaminal. The key step involves ring-opening of the hemiaminal, conjugate addition onto a vinyl sulfonium salt, and epoxidation of the aldehyde by the in situ formed sulfur ylide. Copyright
Phosphine gold(I)-catalyzed hydroamination of alkenes under thermal and microwave-assisted conditions
Liu, Xin-Yuan,Li, Cheng-Hui,Che, Chi-Ming
, p. 2707 - 2710 (2007/10/03)
Phosphine gold(I) complexes catalyzed isomerization of terminal alkenes and hydroamination of unactivated alkenes under thermal and microwave-assisted conditions. This is the first example of the use of microwave radiation as a heat source for gold(I)-catalyzed organic reactions.
Transition Metal Catalyzed Radical Cyclization: New Preparative Route to γ-Lactams from Allylic Alcohols via the -Sigmatropic Rearrangement of Allylic Trichloroacetimidates and the Subsequent Ruthenium-Catalyzed Cyclization of N-Allyltrichloroacetamides
Nagashima, Hideo,Wakamatsu, Hidetoshi,Ozaki, Nobuyasu,Ishii, Tsutomu,Watanabe, Masakazu,et al.
, p. 1682 - 1689 (2007/10/02)
A sequence of reactions including -sigmatropic rearrangement of allyl trichloroacetimidates (Overman rearrangement) followed by ruthenium-catalyzed cyclization of N-allyltrichloroacetamides provided a novel method for preparing trichlorinated γ-lactams from allylic alcohols.No δ-lactam was formed as a byproduct.The cyclization of secondary N-allyltrichloroacetamides proceeded with good diastereoselectivity.Two types of tandem cyclizations to form bicyclic lactams took place in the cyclization of N-allyltrichloroacetamides from geraniol and linalool.
PREPARATION OF 1-TOSYL-2- AND 3-PYRROLIDINONES 'VIA' KETENES AND CARBENES
Saba, Antonio,Selva, Antonio
, p. 867 - 870 (2007/10/02)
Catalytic decomposition of 1-diazo-4-tosylamino-2-butanone 1a, -2-pentanone 1b, and -2-hexanone 1c, results in the quantitative formation of the 1-tosyl-3-pyrrolidinones 2a, 2b and 2c, while the photolysis afforded the rearranged esters, 3a, 3b and 3c, or
