374818-66-3Relevant articles and documents
One-pot access to L-5,6-dihalotryptophans and L-alknyltryptophans using tryptophan synthase
Corr, Michael J.,Smith, Duncan R.M.,Goss, Rebecca J.M.
, p. 7306 - 7310 (2016)
We report, for the first time, the use of tryptophan synthase in the generation of L-dihalotryptophans and L-alkynyltryptophans. These previously unpublished compounds will be useful tools in the generation of probes for chemical biology, in biosynthetic diversification and as convenient building blocks for synthesis.
Rapid Syntheses of Heteroaryl-Substituted Imidazo[1,5-a]indole and Pyrrolo[1,2-c]imidazole via Aerobic C2-H Functionalizations
Kong, Wei-Jun,Chen, Xingrong,Wang, Mingming,Dai, Hui-Xiong,Yu, Jin-Quan
supporting information, p. 284 - 287 (2018/01/17)
Here we report an aerobic Pd(0) catalyzed C2-H functionalization of indoles and pyrroles with tethered N-methoxylamide as the directing group. A Pd(0)-initiated mechanism overcomes the directing or poisoning effect from a wide range of heterocycles including pyridine, pyrimidine, and thiazole. The imidazo[1,5-a]indole products are transformed to bioactive analogs after one-step manipulations, demonstrating the potential utility of this reaction in drug discovery.
Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: Scope of the three-component synthesis of N-aminosulfonamides
Emmett, Edward J.,Richards-Taylor, Charlotte S.,Nguyen, Bao,Garcia-Rubia, Alfonso,Hayter, Barry R.,Willis, Michael C.
supporting information; experimental part, p. 4007 - 4014 (2012/06/04)
By using DABCO·(SO2)2, DABSO, as a solid bench-stable SO2-equivalent, the palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides has been achieved. N,N-Dialkylhydrazines are employed as the N-nucleophiles and provide N-aminosulfonamides as the products in good to excellent yields. The reactions are operationally simple to perform, requiring only a slight excess of SO 2 (1.2-2.2 equiv.), and tolerate a variety of substituents on the halide coupling partner. Variation of the hydrazine component is also demonstrated. The use of N,N-dibenzylhydrazine as the N-nucleophile delivers N-aminosulfonamide products that can be converted into the corresponding primary sulfonamides using a high-yielding, telescoped, deprotection sequence. The ability to employ hydrazine·SO2 complexes as both the N-nucleophile and SO2 source is also illustrated.