21397-03-5Relevant academic research and scientific papers
Mechanochemical Solvent-Free Synthesis of Indenones from Aromatic Carboxylic Acids and Alkynes
Li, Liang,Wang, Guan-Wu
, p. 14102 - 14112 (2021/09/07)
The mechanochemical solvent-free synthesis of indenones from aromatic carboxylic acids and alkynes was achieved through triflic anhydride (Tf2O)-induced cyclization reaction. A variety of indenones including a bioactive PPARγagonist were obtained in up to 90% yield at room temperature. The present protocol has the advantages of mild reaction conditions, high reaction efficiency, and feasibility of scalable synthesis, providing a facile and sustainable route to diverse indenones.
Rhenium-Catalyzed Arylation–Acyl Cyclization between Enol Lactones and Organomagnesium Halides: Facile Synthesis of Indenones
Cheng, Xinyi,Hu, Binjing,Hu, Ying,Karaghiosoff, Konstantin,Li, Jie,Liu, Xingchen
supporting information, p. 15497 - 15502 (2021/06/11)
A set of rhenium-catalyzed arylation–acyl cyclizations between (hetero)arylmagnesium halides and enol lactones through a cascade C(sp2)?C(sp2)/C(sp2)?C(sp2) bond formation under mild reaction conditions has been developed. Indeed, a wide range of functional groups on both organomagnesium halides and enol lactones is well tolerated by the simple rhenium catalysis, thus furnishing polyfunctionalized indenones in one-pot fashion and with complete control of the regioselectivity. Moreover, this approach also provides a straightforward synthetic route to neolignan and (iso)pauciflorol F. Mechanistic studies demonstrated that the reaction involves a sequence of syn-carborhenation and intramolecular nucleophilic addition.
An Approach to One-Pot Regioselective Synthesis of Indenones through Palladium-Catalyzed Annulation in Water
Ramesh, Karu,Satyanarayana, Gedu
, p. 4135 - 4146 (2018/08/11)
A one-pot synthesis of indenones is presented. The process involves palladium-catalyzed annulation of ortho-halobenzaldehydes with internal alkynes. Notably, it proceeded successfully in water as the sole, and green, solvent. Significantly, unlike in earlier reports, this protocol showed excellent regioselectivity with unsymmetrical alkylarylacetylenes. Further, the strategy was extended to a one-pot synthesis of a neolignan natural product.
Palladium-catalyzed annulation of alkynes with ortho -halide-containing benzyl alcohols in aqueous medium
Feng, Jie,Lu, Guoping,Lv, Meifang,Cai, Chun
, p. 10561 - 10567 (2015/02/19)
The Pd-catalyzed annulations of ortho-halide-containing benzyl alcohols with alkynes for the synthesis of indenones were achieved in aqueous Triton X-100 micelles with good yields and wide substrate scopes. Moreover, the indenones obtained in this procedure can be further functionalized to form some more synthetic useful derivatives via an environmental-friendly way.
Polylithiumorganic compounds -19. Regioselective carbon-carbon σ-bond scission followed by a 1,6-proton shift upon the reductive metalation of benzylidenecyclopropane derivatives with lithium metal
Maercker, Adalbert,Daub, Volker E. E.
, p. 2439 - 2458 (2007/10/02)
Depending on the substituent α-substituted benzylidenecyclopropanes (32) react more or less readily with lithium dust (2% sodium) in diethyl ether whereby a regioselective scission of only the cyclopropane σ-bond cis to the phenyl ring takes place. Upon raising the temperature the primarily formed 1,3-dilithiumorganic compound due to an agostic interaction rearranges by a 1,6-proton shift into a doubly bridged 1,4-dilithio compound. With α-methylbenzylidenecyclopropane (32c) this rearrangement was shown to occur intermolecularly via a trilithiumorganic compound 56. The suggested mechanism of these reductive metalation reactions via a bisected radical anion 87 where the lithium is mainly bound to the cyclopropyl carbon atom and oriented syn to the phenyl ring, was supported by MNDO (geometries) and ab initio (energies) calculations.
A NOVEL INDENE SYNTHESIS FROM N-PHENYL-1,1-DIPHENYL-2-ETHYLBUT-3-YNYLAMINE
Ackroyd, John,Pover, Keith A,Scheinmann, Feodor
, p. 5583 - 5584 (2007/10/02)
When N-phenyl-1,1-diphenyl-2-ethylbut-3-ynylamine (1) is treated with 98percent formic acid, 2-ethyl-1-methylene-3-phenyl-1H-indene (4, 56percent) is produced whereas in 50percent formic acid 2-ethyl-1,1-diphenylbut-3-yn-1-ol (98percent, 5)is obtained.
