128342-42-7Relevant academic research and scientific papers
Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics
Drew, Melanie A.,Arndt, Sebastian,Richardson, Christopher,Rudolph, Matthias,Hashmi, A. Stephen K.,Hyland, Christopher J. T.
, p. 13971 - 13974 (2019/11/25)
Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism.
Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds
Fu, Liangbing,Davies, Huw M. L.
supporting information, p. 1504 - 1507 (2017/04/13)
An efficient synthesis of tetrahydrocarboline-type products and polycyclic spiroindolines has been achieved. The transformation proceeds via rhodium(II)-catalyzed intramolecular annulations of indolyl- and pyrrolyl-tethered N-sulfonyl-1,2,3-triazoles. The reaction could be tuned toward either the formal [3 + 2] cycloaddition or the C-H functionalization reaction depending on the electronic and structural features of the substrates, leading to the production of a variety of structurally related heterocyclic compounds.
A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: Syntheses of medium-sized heterocycles
Sun, Yin-Wei,Tang, Xiang-Ying,Shi, Min
, p. 13937 - 13940 (2015/09/07)
The synthesis of medium-sized heterocycles possessing a trans double bond is still a challenge. Herein, gold(I)-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade reaction of furans has been developed, providing highly efficient access to ten- and eleven-membered heterocycles with a broad substrate scope under mild reaction conditions. The reaction outcome features high chemoselectivity at the C5-position of furan. Moreover, a trans-double bond was embodied in the medium ring system.
ON THE MULTIPLICITY OF CARBENES CONJUGATED WITH PYRROLE AND FURAN MOIETIES: MOLECULAR ORBITAL CALCULATION AND REACTION OF 2-(1-METHYL)PYRROLYLMETHYLENE AND 2-FURYLMETHYLENE WITH CIS- AND TRANS-STILBENES
Saito, Katsuhiro,Ushida, Takahiro,Fushihara, Hiroshi,Yamashita, Yoshiro,Tanaka, Shoji,Takahashi, Kensuke
, p. 115 - 122 (2007/10/02)
The reaction of 2-(1-methyl)pyrrolylmethylene and 2-furylmethylene with cis- and trans-stilbenes proceeded in a stereospecific manner to give the corresponding cyclopropane derivatives to show that the multiplicities of these carbenes are singlet.The molecular orbital calculation showed that these carbenes are triplet in their ground state and nucleophilic both in singlet and triplet states.
