139139-72-3Relevant academic research and scientific papers
Silver(I)-Catalyzed Enyne Cyclization/Aromatization of Alkyne-Tethered Cyclohexadienones to Access Meta-Substituted Phenols
Munakala, Anandarao,Chegondi, Rambabu
supporting information, p. 317 - 323 (2021/02/05)
Herein we report a highly regioselective silver(I)-catalyzed intramolecular annulation of alkyne-tethered cyclohexadienones to access meta-substituted phenols with enone functionality, which are difficult to synthesize from conventional methods. The reaction proceeds via intramolecular 1,6-enyne cyclization followed by aromatization and subsequent oxetene ring rearrangement. This strategy has also been compatible with a wide range of C-tethered cyclohexadienones to afford indanes in high yields. The unique functionality of products allows further transformations to expand the diversity.
Lewis Acid-Driven Meyer-Schuster-Type Rearrangement of Yne-Dienone
Mallick, Rajendra K.,Vangara, Srinivas,Kommu, Nagarjuna,Guntreddi, Tirumaleswararao,Sahoo, Akhila K.
, p. 7059 - 7068 (2021/05/29)
Developed herein is a Cu(II)-catalyzed Meyer-Schuster-type rearrangement of alkyne-tethered cyclohexadienone for the construction of m-enone-substituted phenols. The reaction involves an uncommon 5-exo-trig 1,6-enyne cyclization of alkyne-tethered-cyclohexadienone, aromatization-triggered C-O bond cleavage, and an electrocyclic 4π-ring-opening of oxetene intermediate. This atom-efficient transformation provides access to a wide range of synthetically important α-(m-substituted phenol)-α,β-unsaturated ketones, featuring a broad scope with labile functional group tolerance. The gram-scale demonstration makes this transformation synthetically viable. The synthetic application of α,β-unsaturated ketones is also showcased.
Synthesis of cyclobutane-fused oxygen-containing tricyclic framework: Via thermally promoted intramolecular cycloaddition of cyclohexadienone-tethered allenes
Zhai, Shengxian,Qiu, Shuxian,Chen, Lunjian,Niu, Yongsheng,Yu, Youzhu,Yang, Bo,Zhang, Beining,Han, Chuchu,Yang, Liguo,Zhai, Hongbin
supporting information, p. 3405 - 3408 (2020/03/30)
We have developed a unique approach for the thermally promoted cycloaddition of cyclohexadienone-tethered allenes to form a versatile cyclobutane-fused oxygen-containing tricyclic framework in an environmentally friendly and atomic economic fashion with high regioselectivity. The reaction encompasses a broad substrate scope and functional group tolerance of cyclohexadienone moieties. Moreover, the cycloaddition was also applicable to the late-stage functionalization of pharmaceutically relevant compounds.
Tunable arylative cyclization of 1,6-enynes triggered by rhodium(III)-catalyzed C-H activation
Fukui, Yuki,Liu, Ping,Liu, Qiang,He, Zhi-Tao,Wu, Nuo-Yi,Tian, Ping,Lin, Guo-Qiang
supporting information, p. 15607 - 15614 (2014/12/11)
Two tunable arylative cyclizations of cyclohexadienone-containing 1,6-enynes are reported via rhodium(III)-catalyzed C-H activation of O-substituted N-hydroxybenzamides. The use of different O substituents, i.e. O-Piv and O-Me, on the directing group allows the formation of either tetracyclic isoquinolones through an N-Michael addition process or hydrobenzofurans through a C-Michael addition process. Mechanistic investigations of these two cascade reactions clearly indicated that the C-H bond cleavage process was involved in the turnover-limiting step. Furthermore, the cyclization products could be subjected to various transformations for elaborating the pharmaceutically and synthetically valuable potential. This is the first example of a rhodium(III)-catalyzed arylative cyclization reaction of 1,6-enynes, and the results extend the application realm of CpRhIII-catalyzed C-H activation cascade reactions.
Anodic Oxidation of Aryl Propargyl and Aryl Allyl Ethers at a Platinum Electrode
Dhanalekshmii, Savithri,Balasubramanian, Kalpattu Kuppusamy,Venkatachalam, Chittoor Sivamakris.
, p. 6387 - 6400 (2007/10/02)
The oxidation reactions of aromatic 3,3-sigmatropic systems have been investigated under different conditions viz. (a) anodic oxidation in amphiprotic and aprotic media, (b) reaction with (diacetoxyiodo)benzene and (c) reaction promoted by ceric ammonium nitrate.
Electrochemical behaviour of 3,3-sigmatropic systems - Anodic oxidation of aryl allyl ethers and aryl propargyl ethers
Dhanalekshmi,Balasubramanian,Venkatachalam
, p. 7591 - 7592 (2007/10/02)
The electrochemical oxidation of a few methoxy substituted aromatic 3,3-sigmatropic systems yielded mixed quinone monoketals in aqueous methanol and dimerised products in anhydrous acetonitrile.
