106824-45-7Relevant articles and documents
Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles
Martins, Guilherme M.,Zeni, Gilson,Back, Davi F.,Kaufman, Teodoro S.,Silveira, Claudio C.
, p. 3255 - 3261 (2015)
A facile and expedient iodocyclization of 4-(2-prop-1-ynylphenyl)-1H-pyrroles towards the synthesis of polysubstituted 3H-benzo[e]indoles is reported. The transformation was optimized and the best results were obtained by using iodine (1.2 equiv,) in dichloromethane, and potassium carbonate as base. The starting 1,2,3,4-tetrasubstituted pyrroles were efficiently obtained by means of a nickel(II) chloride-promoted four-component (nitromethane, amine, 2-alkynylbenzaldehyde and ethyl acetoacetate) reaction. Further functionalization of the resulting 5-iodoheterocycles was also explored.
Exploiting Hydrazones to Improve the Efficiency of 6π-Electrocyclization Reactions of 1-Azatrienes
Ball-Jones, Matthew P.,Tyler, Jasper,Mora-Radó, Helena,Czechtizky, Werngard,Méndez, María,Harrity, Joseph P. A.
, p. 6821 - 6824 (2019)
The greater geometric lability of hydrazones compared to that of oxime ethers is used as a basis to overcome the reluctance of Z-oxime ether azatrienes to undergo electrocyclization toward the synthesis of borylated (heteroaromatic) pyridines and ring-fused analogues. Such hydrazones now allow access to previously inaccessible tri- and tetrasubstituted 3-borylpyridines in high yields.
Enantioselective Construction of Vicinal Diaxial Styrenes and Multiaxis System via Organocatalysis
Tan, Yu,Jia, Shiqi,Hu, Fangli,Liu, Yidong,Peng, Lei,Li, Dongmei,Yan, Hailong
, p. 16893 - 16898 (2018)
A highly diastereo- and enantioselective methodology for the asymmetric synthesis of vicinal diaxial styrenes and multiaxis system was achieved by organocatalysis. Various vicinal diaxial styrenes and multiaxis systems were obtained in excellent enantioselective manners. The mechanism studies revealed that a new tetra-substituted vinylidene ortho-quinone methide (VQM) intermediate was likely involved and accounted for the excellent enantioselectivity.
Rhodium-catalyzed regio- and enantioselective intermolecular [4+2] carbocyclization of 4-alkynals with N,N-dialkyl acrylamides
Tanaka, Ken,Hagiwara, Yuji,Noguchi, Keiichi
, p. 7260 - 7263 (2005)
(Chemical Equation Presented) Selective rings: A cationic Rh I-(R,R)-walphos complex catalyzes a highly regio-and enantioselective intermolecular [4+2] carbocyclization of 4-alkynals with N,N-dialkyl acrylamides to afford enantioenriched cyclohexanones (see scheme; cod = cycloocta-1,5-diene). This new route is attractive in view of the one-step access to 4-alkynals from commercially available reagents.
A versatile aminobenzannulation method based on the deprotonation of 2-(1-alkynyl)-benzaldimines and similar 2-aza-2,4-heptadienyl-6-ynes: A multistep rearrangement cascade
Sagar, Pramod,Froehlich, Roland,Wuerthwein, Ernst-Ulrich
, p. 5694 - 5697 (2004)
Two ring closures, a ring opening, and two intermolecular proton shifts are the crucial steps in a cascade reaction that is triggered by the simple deprotonation of alkynylimines and leads ultimately to aminobenzannulation products (see scheme). The reactions proceed in good to very good yield and with excellent chemoselectivity.
Generation and trapping of isobenzofuran intermediates formed in the coupling of Fischer carbene complexes and o-alkynylbenzoyl derivatives
Jiang, Delu,Herndon, James W.
, p. 1267 - 1269 (2000)
(equation presented) The coupling of o-alkynylbenzoyl derivatives with carbene complexes has been investigated. The reaction initially affords isobenzofuran derivatives, which convert to alkylidenephthalan derivatives or can be trapped by various dienophi
Design and Synthesis of Fused Pyridine Building Blocks for Automated Library Generation
Mora-Radó, Helena,Czechtizky, Werngard,Méndez, María,Harrity, Joseph P. A.
supporting information, p. 328 - 334 (2020/12/17)
We demonstrate that a diboration-electrocyclization sequence provides access to a range of pyridine-fused, small-molecule boronic ester building blocks, and that these are amenable to high-throughput synthesis leading to biaryl and ether-linked compound libraries. Moreover, the implementation of an integrated physicochemical and ADME profiling workflow allows accelerated design of novel lead compounds for application in drug-discovery projects.
Radical Cascade Bicyclization/Aromatization of 1,7-Enynes with 1,3-Dicarbonyl Compounds towards 2,3-Dihydro-1H-cyclopenta[a]naphthalenes
Cai, Tao,Chen, Jianhui,Chen, Xinyu,Gao, Yuzhen,Li, Peiqin,Ni, Yuqi,Shen, Runpu,Sun, Tao,Wu, Chunlei,Xu, Huiting,Xu, Yanfei,Zhang, Zhebing
supporting information, p. 3750 - 3755 (2021/07/09)
An Ag-catalyzed radical cascade bicyclization/aromatization of C-linked 1,7-enynes with 1,3-dicarbonyls has been achieved, providing a step- and atom-economy approach for the construction of 2,3-dihydro-1H-cyclopenta[a]naphthalenes, an important structural scaffold existed in biologically active compounds. From this transformation, structurally diverse 2,3-dihydro-1H-cyclopenta[a]naphthalenes were obtained in moderate to good yields with high regioselectivity. Moreover, the further product derivatizations were also exemplified. (Figure presented.).