76537-07-0Relevant academic research and scientific papers
Ruthenium(II)-Catalyzed Regioselective Ortho Amidation of Imidazo Heterocycles with Isocyanates
Shakoor, S. M. Abdul,Kumari, Santosh,Khullar, Sadhika,Mandal, Sanjay K.,Kumar, Anil,Sakhuja, Rajeev
, p. 12340 - 12349 (2016)
Direct ortho amidation at the phenyl ring of 2-phenylimidazo heterocycles with aryl isocyanates has been achieved via a chelation-assisted cationic ruthenium(II) complex catalyzed mechanism. The methodology provides a straightforward, high-yielding regios
Magnetically Bistable Nitrenes: Matrix Isolation of Furoylnitrenes in Both Singlet and Triplet States and Triplet 3-Furylnitrene
Feng, Ruijuan,Lu, Yan,Deng, Guohai,Xu, Jian,Wu, Zhuang,Li, Hongmin,Liu, Qian,Kadowaki, Norito,Abe, Manabu,Zeng, Xiaoqing
, p. 10 - 13 (2018)
Two simple acylnitrenes, 2-furoylnitrene (2) and 3-furoylnitrene (6), were generated through 266 nm laser photolysis of the corresponding azides. Both are magnetically bistable in cryogenic matrices, as evidenced by the direct observation of the closed-shell singlet state with IR spectroscopy in solid Ne, Ar, Kr, Xe, and N2 matrices (3-40 K) and the triplet state in toluene (10 K) with EPR spectroscopy (32: |D/hc| = 1.48 cm-1 and |E/hc| = 0.029 cm-136: |D/hc| = 1.39 cm-1 and |E/hc|c = 0.039 cm-1). Subsequent visible-light and UV laser irradiations led to the formation of furyl isocyanates (3 and 7) and ring-opening product 3-cyanoacrolein (9-E and 9-Z), respectively, in which the elusive 3-furylnitrene (38) was also identified by IR and EPR spectroscopy (|D/hc| = 1.12 cm-1 and |E/hc| = 0.005 cm-1).
Eight-Step Enantioselective Total Synthesis of (?)-Cycloclavine
McCabe, Stephanie R.,Wipf, Peter
supporting information, p. 324 - 327 (2016/12/30)
The first enantioselective total synthesis of (?)-cycloclavine was accomplished in 8 steps and 7.1 % overall yield. Key features include the first catalytic asymmetric cyclopropanation of allene, mediated by the dirhodium catalyst Rh2(S-TBPTTL)4, and the enone 1,2-addition of a new TEMPO carbamate methyl carbanion. An intramolecular strain-promoted Diels–Alder methylenecyclopropane (IMDAMC) reaction provided a pivotal tricyclic enone intermediate with more than 99 % ee after crystallization. The synthesis of (?)-1 was completed by a late-stage intramolecular Diels–Alder furan (IMDAF) cycloaddition to install the indole.
1-propanephosphonic acid cyclic anhydride (T3P) as an efficient promoter for the Lossen rearrangement: Application to the synthesis of urea and carbamate derivatives
Vasantha, Basavalingappa,Hemantha, Hosahalli P.,Sureshbabu, Vommina V.
experimental part, p. 2990 - 2996 (2010/10/21)
The synthesis of hydroxamic acids starting from carboxylic acids employing 1-propanephosphonic acid cyclic anhydride (T3P) activation is described. Application of ultrasonication accelerates this conversion. Further, the T3P has also been employed to activate the hydroxamates, leading to isocyanates via the Lossen rearrangement. The isocyanates were trapped with suitable nucleophiles to afford the corresponding ureas and carbamates. Georg Thieme Verlag Stuttgart New York.
A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines
Padwa, Albert,Brodney, Michael A.,Liu, Bing,Satake, Kyosuke,Wu, Tianhua
, p. 3595 - 3607 (2007/10/03)
The intramolecular Diels-Alder reaction of 2-substituted aminofurans (IMDAF) results in the formation of various indolines and tetrahydroquinolines. The isolation of these ring systems from the IMDAF reaction can be rationalized in terms of an initial [4 + 2]-cycloaddition that first produces an oxa-bridged cycloadduct, which was not detected since it readily underwent nitrogen-assisted ring opening. Proton exchange followed by an eventual dehydration provides the aromatic product. In certain cases, the intermediate cyclohexadienol can be isolated and independently converted to the final product in high yield. The starting 2-aminofurans were readily prepared from furanyl acyl azide by a Curtius rearrangement in the presence of an alcohol. Alkylation of the resulting N-alkyl carbamate with an alkenyl bromide allows for the synthesis of a wide variety of cycloaddition precursors. The scope of the IMDAF reaction was evaluated by using mono- and disubstituted alkenes, electron rich and electron deficient olefins, and acetylenic tethers. Cyclic 2-amidofurans were also synthesized using a related intramolecular Diels-Alder reaction of 2-amido-substituted oxazoles which contain a tethered alkyne. This transformation represents a new route to this rare heterocyclic ring system. The sequential cycloaddition method was used for a formal synthesis of the pyrrolophenanthridone alkaloid hippadine.
MICROWAVE SPECTRA OF CIS AND TRANS 2-FURYLISOCYANATE CONFORMERS
Masson, Michel Andre,Bouchy, Alain,Dormoy, Jean Robert,Roussy, Georges
, p. 11 - 18 (2007/10/02)
The microwave spectrum of 2-furylisocyanate has been obtained in the frequency region from 8 to 40 GHz.This spectrum is attributed to the ground state of the cis and trans configurations.The rotational constants for both ground vibrational states have been determined.Two sets of vibrational satellites are observed and assigned to the modes of C-N torsion and CNC bending.The microwave results show and MINDO/3 calculations confirm that the barrier between the cis and trans conformers is high and that the cis conformer is more stable than the trans by 3 kcal mol-1.
SYNTHESE ET THERMOLYSE DE DERIVES DISILYLES DES ACIDES HYDROXAMIQUES: SUR UNE NOUVELLE VOIE D'ACCES AUX ESTERS ISOCYANIQUES ET AUX AMINES
Rigaudy, J.,Lytwyn, E.,Wallach, P.,Cuong, Nguyen Kim
, p. 3367 - 3370 (2007/10/02)
Thermolysis of disilylated hydroxamic acids 7, readily prepared from hydroxamic acids 5 and hexamethyl disilazane, leads to the corresponding isocyanates 4; an application to the synthesis of amines is reported.
