159763-31-2Relevant articles and documents
Organocatalyzed Decarboxylative Trichloromethylation of Morita–Baylis–Hillman Adducts in Batch and Continuous Flow
Enevoldsen, Martin V.,Overgaard, Jacob,Pedersen, Maja S.,Lindhardt, Anders T.
, p. 1204 - 1208 (2018/02/06)
Two protocols for the organocatalyzed decarboxylative trichloromethylation of Morita–Baylis–Hillman (MBH) substrates have been developed. Applying sodium trichloroacetate, as the trichloromethyl anion precursor, in combination with an organocatalyst and a
N-bromosuccinimide-mediated radical cyclization of 3-arylallyl azides: Synthesis of 3-substituted quinolines
Wang, Wei-Xia,Zhang, Qing-Zhao,Zhang, Tian-Qi,Li, Zhan-Shan,Zhang, Wei,Yu, Wei
, p. 221 - 226 (2015/02/19)
Visible light irradiation of N-bromosuccinimide serves as an effective means to convert methyl 2-(azidomethyl)-3-arylpropenoates and 2-(azidomethyl)-3-arylacrylonitriles to the corresponding iminyl radicals via ?±-hydrogen abstraction and subsequent extrusion of dinitrogen. Thus formed iminyl radicals then undergo intramolecular ortho attack on the aryl ring, affording methyl quin-oline-3-carboxylates and quinoline-3-carbonitriles respectively.
Iodine-mediated intramolecular electrophilic aromatic cyclization in allylamines: A general route to synthesis of quinolines, pyrazolo[4,3-b] pyridines, and thieno[3,2-b]pyridines
Batchu, Harikrishna,Bhattacharyya, Soumya,Batra, Sanjay
supporting information, p. 6330 - 6333 (2013/02/23)
An unprecedented synthesis of aromatic ring annulated pyridines from suitably substituted primary allylamines via intramolecular electrophilic aromatic cyclization mediated by molecular iodine under mild conditions is described.
Synthesis of 2-amino-3,4-dihydroquinazolines and imidazo[2,1-b]quinazoline- 2-ones
Mishra, Amita,Batra, Sanjay
scheme or table, p. 3077 - 3088 (2009/12/28)
A straightforward method for the synthesis of 2-amino-3,4- dihydroquinazolines from Baylis-Hillman derivatives is disclosed. The protocol involves sequential SN2 reaction of a primary amine on the Baylis-Hillman acetate derived from 2-nitrobenzaldehyde, c
Preparation of 2-Quinolones by sequential heck reduction-cyclization (HRC) reactions by using a multitask palladium catalyst
Felpin, Francois-Xavier,Coste, Jerome,Zakri, Cecile,Fouquet, Eric
experimental part, p. 7238 - 7245 (2010/03/25)
One-pot sequential Heck reduction-cyclization (HRC) reactions leading to the synthesis of substituted 2-quinolones have been developed by using a heterogeneous or mixed homogeneous/heterogeneous multitask palladium catalyst with charcoal as a support. The whole sequence occurs under very mild conditions without the need for additives (ligand or base) by taking advantage of the high reactivity of aryldiazonium salts as "super electrophiles". Recycling experiments showed that the reused heterogeneous Pd°/C catalyst was not able to promote another HRC sequence but was, however, still highly active for hydrogenation, hydrodehalogenation, as well as hydrogenolysis reactions.
Straightforward strategy for the stereoselective synthesis of spiro-fused (C-5)isoxazolino- or (C-3)pyrazolino-(C-3)quinolin-2-ones from Baylis-Hillman adducts by 1,3-dipolar cycloaddition and reductive cyclization
Singh, Virender,Singh, Vijay,Batra, Sanjay
scheme or table, p. 5446 - 5460 (2009/05/11)
A straightforward and general approach for the stereoselective synthesis of spiro-fused (C-5)isoxazolino- or (C-3)pyrazolino-(C-3)quinolin-2-ones from the adducts offorded from the Baylis-Hillman reaction of 2-nitrobenzaldehyde and ethyl acrylate by sequential 1,3-dipolar cycloaddition and reductive cyclization is presented. It was found that the reductive cyclization of the isoxazoline derivatives proceeded efficiently in the presence of In/HCl, whereas similar reductions of pyrazolines gave better yields when carried out in the presence of an Fe/AcOH mixture. However, similar attempts employing the Baylis-Hillman adduct of 2-nitrobenzaldehyde and methyl vinyl ketone did not yield the desired compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Synthesis of substituted 1H- and 3H-1-benzazepines and rearrangement of alkyl 1H-1-benzazepine-2-carboxylates into isoquinolines
Singh, Vijay,Batra, Sanjay
, p. 2970 - 2976 (2008/02/10)
The SnCl2-mediated reduction of nitro groups in 2-nitro-4-(2-nitrobenzylidene)alkanoates and 4-nitro-2-(2-nitroalkylidene) alkanoates allows the facile synthesis of substituted 1H-1-benzazepines and 3H-1-benzazepines. This reaction proceeds via
An alternate approach to quinoline architecture via Baylis-Hillman chemistry: SnCl2-mediated tandem reaction toward synthesis of 4-(substituted vinyl)-quinolines
Madapa, Sudharshan,Singh, Virender,Batra, Sanjay
, p. 8740 - 8747 (2007/10/03)
An alternate approach to densely substituted quinolines from the products of SN2 nucleophilic substitution reaction between the acetyl derivatives of the Baylis-Hillman adducts obtained from 2-nitrobenzaldehydes and the carbonyl group containin
Synthesis of methyl (E)-2-nitromethylcinnamates derived from baylis-hillman acetates and conversion into several coumarin derivatives
Hong, Wan Pyo,Lee, Kee-Jung
, p. 33 - 38 (2007/10/03)
Fast and easy access to methyl (E)-2-nitromethylcinnamates, from the corresponding Baylis-Hillman acetates with NaNO2 in DMF is described. Several ortho-chloro-2-nitromethylcinnamates undergo intramolecular aromatic substitution reaction follow
Some mechanistic and synthetic aspects of the DABCO catalysed rearrangement of allylic esters
Mason, Paul H.,Emslie, Neville D.
, p. 12001 - 12008 (2007/10/02)
Experimental evidence shows that the DABCO catalysed rearrangement of allylic esters proceeds via a two path mechanism, rather than a single path, as has been previously proposed. The effectiveness of other catalysts as well as E:Z ratios for these DABCO catalysed reactions have also been determined.
