80778-47-8Relevant articles and documents
Pd(II)-Catalyzed Intramolecular C(sp2)-H Arylation of Tryptamines Using the Nonsteric NH2as a Directing Group
Wang, Sixi,Yu, Bin,Liu, Hong-Min
supporting information, p. 42 - 48 (2021/01/09)
The free amine-directed C-H functionalization reactions are challenging and mainly restricted to bulky amines. In this work, we report the nonsteric NH2-directed Pd(II)-catalyzed intramolecular C(sp2)-H arylation of tryptamines, which enables the efficient, gram-scale, and regioselective synthesis of versatile 2-aryltryptamines (35 examples, up to 98% yield). This approach broadens the substrate scope of the free amine-directed C-H functionalization, not limited to bulky amine substrates. Late-stage elaborations of 2-aryltryptamines achieve the divergent construction of the complex core structures that are prevalent in highly valuable natural products such as aurantioclavine, chimonanthine, and phalarine.
Design, synthesis, and structure–activity relationship studies of the anaephene antibiotics
Kukla, David L.,Canchola, Juan,Rosenthal, Joseph D.,Mills, Jonathan J.
, p. 295 - 304 (2021/06/25)
The natural products, anaephenes A (1) and B (2), were found to have antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA). In this report, we expanded on our previous synthetic efforts by preparing a library of eighteen analogues in order to understand the structure–activity relationships (SAR) of this interesting class of natural products. These analogues were selected to explore the biological impact of structural variations in the alkyl chain and on the phenol moiety. Last, we further assessed the biological activity of anaephene B (2) and two additional analogues against other clinically relevant bacterial strains and the hemolytic activity of each and determined that these compounds act via a bactericidal mechanism. These studies led to the identification of compound 7, which was 4-fold more potent than the natural product (2) against MRSA (2 vs. 8?μg/ml) and a 2-hydroxypyridine analogue (18) which demonstrated equal potency compared with the natural product (2), albeit with a significant reduction in hemolytic activity (1% vs. 80% at 100?μM).
Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes
Liang, Hao,He, Xiaobo,Zhang, Yaqi,Chen, Bin,Ouyang, Jia-Sheng,Li, Yongsu,Pan, Bendu,Subba Reddy, Chitreddy V.,Chan, Wesley Ting Kwok,Qiu, Liqin
supporting information, p. 11429 - 11432 (2020/10/12)
The copper(ii)-catalyzed (4+1) cyclizations and copper(i)-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes were successfully developed by employing efficient and safe iodonium ylides instead of traditional diazo compounds. Highly functionaliz
Synthesis of indole-fused heteroacenes by cascade cyclisation involving rhodium(ii)-catalysed intramolecular C-H amination
Matsuda, Takanori,Ito, Hirotaka
supporting information, p. 6703 - 6707 (2018/09/29)
Heteroacenes are potentially important materials for organic electronics and their syntheses are of topical interest. Herein we report the development of a catalytic, redox-neutral reaction for the synthesis of the 5,10-dihydroindolo[3,2-b]indole class of
Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings
Perry, Gregory J. P.,Quibell, Jacob M.,Panigrahi, Adyasha,Larrosa, Igor
, p. 11527 - 11536 (2017/08/30)
Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.
Gold-Catalyzed Domino Synthesis of Functionalized Benzofurans and Tetracyclic Isochromans via Formal Carboalkoxylation
Obata, Tomoyuki,Suzuki, Sho,Nakagawa, Asuka,Kajihara, Ryota,Noguchi, Keiichi,Saito, Akio
supporting information, p. 4136 - 4139 (2016/08/30)
A domino synthesis of benzofurans with the modification of side chains from α-alkoxyalkyl o-alkynylaryl ethers (n = 0) and electron-rich arenes has been developed. In the present domino reaction, which would proceed via the α-alkoxyalkylation of arenes with an intermediate in the migratory cycloisomerization of o-alkynylaryl ethers followed by the nucleophilic addition of benzofurans to benzyl ethers, a cationic Au(III) catalyst activates the C-C π bond and the C-O σ bond. The present method could be extended to Au(I)-catalyzed domino synthesis of tetracyclic isochromans from α-alkoxyalkyl (o-alkynylaryl)methyl ethers (n = 1) and aryl methoxymethyl ethers.
Enantioselective intramolecular cyclization of alkynyl esters catalyzed by a chiral Br?nsted base
Kondoh, Azusa,Tran, Hoa Thi Quynh,Kimura, Kyoko,Terada, Masahiro
supporting information, p. 5726 - 5729 (2016/05/19)
An enantioselective intramolecular cyclization reaction of alkynyl esters was developed, which employs a Br?nsted base catalyst generated in situ from a chiral Schiff base and t-BuOK. This reaction is a rare example of the enantioselective intramolecular addition of simple ester enolates to alkynes under Br?nsted base catalysis.
Dual Photoredox/Gold Catalysis Arylative Cyclization of o-Alkynylphenols with Aryldiazonium Salts: A Flexible Synthesis of Benzofurans
Xia, Zhonghua,Khaled, Omar,Mouriès-Mansuy, Virginie,Ollivier, Cyril,Fensterbank, Louis
, p. 7182 - 7190 (2016/08/30)
A new method for the arylative cyclization of o-alkynylphenols with aryldiazonium salts via dual photoredox/gold catalysis is described. The reaction proceeds smoothly at room temperature in the absence of base and/or additives and offers an efficient app
Glucocorticoid receptor modulators informed by crystallography lead to a new rationale for receptor selectivity, function, and implications for structure-based design
Carson, Matthew W.,Luz, John G.,Suen, Chen,Montrose, Chahrzad,Zink, Richard,Ruan, Xiaoping,Cheng, Christine,Cole, Harlan,Adrian, Mary D.,Kohlman, Dan T.,Mabry, Thomas,Snyder, Nancy,Condon, Brad,Maletic, Milan,Clawson, David,Pustilnik, Anna,Coghlan, Michael J.
, p. 849 - 860 (2014/03/21)
The structural basis of the pharmacology enabling the use of glucocorticoids as reliable treatments for inflammation and autoimmune diseases has been augmented with a new group of glucocorticoid receptor (GR) ligands. Compound 10, the archetype of a new f
Alkoxyboration: Ring-closing addition of B-O σ bonds across alkynes
Hirner, Joshua J.,Faizi, Darius J.,Blum, Suzanne A.
supporting information, p. 4740 - 4745 (2014/04/17)
For nearly 70 years, the addition of boron-X σ bonds to carbon-carbon multiple bonds has been employed in the preparation of organoboron reagents. However, the significantly higher strength of boron-oxygen bonds has thus far precluded their activation for addition, preventing a direct route to access a potentially valuable class of oxygen-containing organoboron reagents for divergent synthesis. We herein report the realization of an alkoxyboration reaction, the addition of boron-oxygen σ bonds to alkynes. Functionalized O-heterocyclic boronic acid derivatives are produced using this transformation, which is mild and exhibits broad functional group compatibility. Our results demonstrate activation of this boron-O σ bond using a gold catalysis strategy that is fundamentally different from that used previously for other boron addition reactions.
