73252-54-7Relevant academic research and scientific papers
Synthesis of polymethoxy-substituted triazolobenzoxazepines
Bukhvalova, S. Yu.,Ivanov,Malysheva, Yu. B.,Fedorov, A. Yu.
, p. 1481 - 1489 (2016/11/29)
A new approach has been proposed for the synthesis of polymethoxy-substituted [1,2,3]triazolo-[1,5-a][4,1]benzoxazepines starting from 2-bromo-4,5-dimethoxy- and 2-bromo-3,4,5-dimethoxybenzyl alcohols with thermal [3 + 2]-dipolar cycloaddition as the key stage.
CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: An efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a] quinazolines
Kiruthika, Selvarangam E.,Perumal, Paramasivan Thirumalai
supporting information, p. 484 - 487 (2014/04/03)
A Cu(I)-catalyzed, intermolecular protocol for the synthesis of 2-amidoindoles and tetrahydroindolo[1,2-a]quinazolines in shorter time and high yields is reported. The key highlight of this disclosure is the formation of 2-amidoindole and tetrahydroindolo[1,2-a]quinazoline moieties directly from gem-dibromovinylanilides and sulfonamides in a one-pot fashion through the in situ formation of ynamides followed by a base-promoted intramolecular hydroamidation.
Sequential one-pot method for oxy-Michael addition, Heck coupling, and degradation followed by condensation: Facile synthesis of 2-benzoxepin-3(1H)- ones Dedicated to the memory of my teacher Professor P.V. Subba Rao, Department of Chemistry, Andhra University, Visakhapatnam
Reddy, A. Gopi Krishna,Krishna,Satyanarayana
supporting information, p. 10098 - 10107 (2013/11/06)
A sequential one-pot intermolecular oxy-Michael addition, intermolecular Heck coupling, and intramolecular degradation (retro-oxy-Michael addition) followed by condensation method has been developed for the synthesis of interesting 2-benzoxepin-3(1H)-ones. Significantly, the 2-benzoxepin-3(1H)-ones form the core quantum of biologically vital natural products. The initial oxy-Michael addition and Heck coupling steps involve a straight forward construction of C-O and C-C bonds, whereas, the final condensation step follows a novel mechanistic path via intramolecular degradation, double bond isomerization, and intramolecular condensation. Notably, a remarkable solvent effect has been observed in-order to promote the final intramolecular condensation.
An efficient sequential one-pot base mediated C-O and Pd-mediated C-C bond formation: Synthesis of functionalized cinnamates and isochromenes
Gopi Krishna Reddy,Krishna,Satyanarayana
supporting information, p. 5635 - 5640 (2012/10/29)
An efficient sequential one-pot intermolecular oxy-Michael addition and intermolecular Heck coupling for the synthesis of functionalized cinnamates is presented. Bulky tert-butyl acrylate was identified as a more suitable Michael acceptor for initial oxy-Michael addition, as it precludes the formation of undesired cross condensed ester. Most importantly, the present method was further divergently extended to the successful synthesis of isochromenes via a sequential one-pot O-allylation and subsequent intramolecular Heck cyclization.
A novel anionic domino process for the synthesis of o-cyanoaryl-methylthio/ alkyl/aryl/heteroaryl acetylenes
Kumar, Sarvesh,Peruncheralathan, Saravanan,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
supporting information; experimental part, p. 965 - 968 (2009/04/10)
A novel unexpected anionic domino process involving n-BuLi-induced rearrangement of 3,3-bis(methylthio) or 3-methylthio-3-aryl heteroaryl. alkyl-o-bromoarylacrylonitriles to ocyanoarylacetylenes in synthetically useful yields has been reported. The scope and generality of the reaction has been examined, and a possible mechanism has been proposed.
Diversity oriented microwave-assisted synthesis of (-)-steganacin aza-analogues
Mont, Nuria,Mehta, Vaibhav Pravinchandra,Appukkuttan, Prasad,Beryozkina, Tetyana,Toppet, Suzzane,Van Hecke, Kristof,Van Meervelt, Luc,Voet, Arnout,DeMaeyer, Marc,Van Der Eycken, Erik
, p. 7509 - 7516 (2008/12/22)
(Chemical Equation Presented) A novel microwave-assisted, highly efficient protocol for the synthesis of hitherto unknown aza-analogues of (-)-Steganacin, a naturally occurring bisbenzocyclooctadiene lignan lactone with potent antileukemic and tubulin polymerization inhibitory activity, has been developed. Focused microwave irradiation is demonstrated to be highly beneficial in promoting the three crucial steps of the sequence to effect the final ring closure: the Suzuki-Miyaura reaction, Cu-mediated A3-coupling, as well as the intramolecular Huisgen 1,3-dipolar cycloaddition.
Chiral oxazoline route to enantiomerically pure biphenyls: Magnesio and copper mediated asymmetric hetero- and homo-coupling reactions
Meyers,Nelson, Todd D.,Moorlag, Henk,Rawson, David J.,Meier, Anton
, p. 4459 - 4473 (2007/10/03)
A series of chiral biphenyls were prepared via asymmetric reactions involving chiral oxazolines. One series of chiral biphenyls was reached by the magnesium mediated coupling of aryl bromides (via their Grignard reagents) with o-methoxyaryl oxazolines. In
A New Synthesis of Phthalides by Internal Trapping in Ortho-Lithiated Carbamates Derived from Benzylic Alcohols
Paleo, M. Rita,Lamas, Carlos,Castedo, Luis,Dominguez, Domingo
, p. 2029 - 2033 (2007/10/02)
The addition of t-BuLi to a low-temperature THF solution of o-bromocarbamates 2 leads to ortho-lithiated intermediates 3, in which internal trapping by the electrophile on the side chain then takes place.This novel Parham-type anionic cyclization procedure affords the variously substituted phthalides 5 in high yields and can also be used for the preparation of lactones 8, which are useful for the synthesis of aristocularine alkaloids.
The Ambient Temperature Ullmann Reaction and Its Application to the Total Synthesis of (+/-)-Steganacin
Ziegler, Frederick E.,Chliwner, Irene,Fowler, Kerry W.,Kanfer, Sheldon J.,Kuo, Stephen J.,Sinha, Nanda D.
, p. 790 - 798 (2007/10/02)
The details of a new method for preparing unsymmetrical biphenyls at room temperature by a modification of the classical Ullmann reaction are discussed.An intramolecularly coordinated organocopper reagent is treated with an aryl iodide bearing a potential coordinating ligand to form the biphenyl.Nitrogen and sulfur have been utilized as ligands and as protecting groups for carbonyls.The application of this methodology to the synthesis of the antileukemic steganacin is detailed.
