58106-57-3Relevant academic research and scientific papers
A Diastereoselective Route to Benzoannelated Bridged Sultams
Klochkova, Anastasiia A.,Rassadin, Valentin A.,Sokolov, Victor V.
supporting information, p. 4484 - 4494 (2021/08/13)
A practical diastereoselective method for the synthesis of benzoannelated tri- and tetracyclic bridged sultams has been developed. The synthetic route employs widely available, substituted -iodoanilines and is based on intramolecular Michael addition followed by cycloalkylation with dihaloalkanes, or vice versa. The target compounds were isolated in good yields and the diastereoselectivity of the reaction could be easily controlled by the order of Michael addition and cycloalkylation steps.
Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes
Pitchumani, Venkatachalam,Breugst, Martin,Lupton, David W.
supporting information, p. 9413 - 9418 (2021/12/09)
β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.
Cross-Cycloaddition of Two Different Isocyanides: Chemoselective Heterodimerization and [3+2]-Cyclization of 1,4-Diazabutatriene
Hu, Zhongyan,Yuan, Haiyan,Men, Yang,Liu, Qun,Zhang, Jingping,Xu, Xianxiu
, p. 7077 - 7080 (2016/07/06)
A new cross-cycloaddition reaction between a wide range of isocyanides and 2-isocyanochalcones (or analogues) was developed for the expeditious synthesis of pyrrolo[3,4-b]indoles under thermal conditions. On the basis of the experimental results and DFT c
Highly enantioselective intramolecular 1,3-dipolar cycloaddition: A route to piperidino-pyrrolizidines
Vidadala, Srinivasa Rao,Golz, Christopher,Strohmann, Carsten,Daniliuc, Constantin-G.,Waldmann, Herbert
supporting information, p. 651 - 655 (2015/03/04)
Enantioselective catalytic intermolecular 1,3-dipolar cycloadditions are powerful methods for the synthesis of heterocycles. In contrast, intramolecular enantioselective 1,3-dipolar cycloadditions are virtually unexplored. A highly enantioselective synthesis of natural-product-inspired pyrrolidino-piperidines by means of an intramolecular 1,3-dipolar cycloaddition with azomethine ylides is now reported. The method has a wide scope and yields the desired cycloadducts with four tertiary stereogenic centers with up to 99% ee. Combining the enantioselective catalytic intramolecular 1,3-dipolar cycloaddition with a subsequent diastereoselective intermolecular 1,3-dipolar cycloaddition yielded complex piperidino-pyrrolizidines with very high stereoselectivity in a one-pot tandem reaction.
Rhodium(III)-catalyzed in situ oxidizing directing group- assisted c-h bond activation and olefination: A route to 2-vinylanilines
Muralirajan, Krishnamoorthy,Haridharan, Radhakrishnan,Prakash, Sekar,Cheng, Chien-Hong
, p. 761 - 766 (2015/03/18)
A new and efficient method for the synthesis of 2-vinylanilines from the reaction of arylhydrazine hydrochlorides with alkenes and diethyl ketone via a rhodium-catalyzed C-H activation is described. The oxidant-free olefination reaction involves the in situ generation of an -N-N=CR1R2 moiety as the oxidizing directing group thus providing an easy access to 2-vinylanilines.
Rhodium-catalyzed tandem conjugate addition-Mannich cyclization reaction: Straightforward access to fully substituted tetrahydroquinolines
So, Won Youn,Song, Ju-Hyun,Jung, Dai-Il
, p. 5658 - 5661 (2008/12/21)
(Chemical Equation Presented) A new Rh(I)-catalyzed tandem conjugate addition-Mannich cyclization reaction of imine-substituted electron-deficient alkenes with arylboronic acids has been developed to afford 2,3,4-trisubstituted 1,2,3,4-tetrahydroquinolines. This is the first example involving imine group as a secondary electrophile in Rh(I)-catalyzed tandem reactions.
BASIC MEDIA BEHAVIOR OF N- ETHYL CARBAMATES (Y=SMe, SOMe, SO2Me, H, Br, CN)
Ruano, Jose Luis Garcia,Pedregal, Concepcion,Rodriguez, Jesus H.
, p. 203 - 214 (2007/10/02)
From the results obtained in the hydrolysis reaction of the carbamate group of some thioderivatives compounds whose common structure is (2-EtOOCNH-C6H4)-CHOH-CH2Y a mechanism is suggested to explain the products, as well as the relationship between the relative configuration of diastereoisomeric sulfoxides (Y=SOMe) with the reaction rate and with the stereochemical outcome.Other interesting and unexpected products are yielded when the hydrolysis reaction of other carbamates (Y=H, Br, CN) is carried out.In the present cases, the carbamate function seems to behave as a very versatile group capable of readily undergoing conversions to several kinds of heterocycles.
