1309934-63-1Relevant academic research and scientific papers
A convenient allenoate-based synthesis of 2-quinolin-2-yl malonates and β-ketoesters
Selig, Philipp,Raven, William
, p. 5192 - 5195 (2014)
N-Protected o-aminobenzaldehydes smoothly react with α,γ-dialkylallenoates under Bronsted basic conditions to yield 2,3-disubstituted quinolines. This three-step reaction cascade of Michael addition, aldol condensation, and 1,3-N → C rearrangement uses the complete protecting group as a building block in a highly efficient C,C-bond formation of a new all-carbon quaternary center. Carbamate protected substrates (N-Boc, N-Cbz, N-Alloc) thus give 2-quinolin-2-yl-malonates, while amide protected substrates (N-Ac, N-Bz) afford 2-quinolin-2-yl-β-ketoesters in high yields.
Designing and Accurately Developing a [6 + 2] Dipolar Cycloaddition for the Synthesis of Benzodiazocines
Cai, Wei,Chen, Kaihong,He, Yanlin,Huang, You,Yu, Cui,Zhou, Yiming
, p. 5430 - 5434 (2021/07/26)
1,6-Dipolar cycloadditions represent a valuable strategy for the rapid construction of medium-sized rings. Herein, we describe the concept for the design of 1,6-dipoles that bypasses the regioselectivity. Through the introduction of an amino group into Morita-Baylis-Hillman (MBH) carbonates, unprecedented [6 + 2] dipolar cycloadditions were accurately developed with Cs2CO3, efficiently delivering a series of benzodiazocines in mild conditions. Computational studies bring a deeper understanding of this reaction.
DABCO catalyzed [4+2] annulations of Morita-Baylis-Hillman carbonates with isocyanates
Cai, Wei,He, Yanlin,Huang, You,Zhou, Yiming
, p. 8985 - 8988 (2021/09/13)
A highly concise method for 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed [4+2] annulations ofo-amino-acylation of aryl MBH carbonates with isocyanates has been developed. For the first time, MBH carbonates served as 1,4-dipoles, providing functionalized 3,4-dihydroquinazolinones in mild conditions with good to excellent yields. The density functional theory calculations of the mechanism supports our hypothesis.
Rhodium-catalyzed cycloisomerization involving cyclopropenes: Efficient stereoselective synthesis of medium-sized heterocyclic scaffolds
Miege, Frederic,Meyer, Christophe,Cossy, Janine
supporting information; experimental part, p. 5932 - 5937 (2011/08/02)
A happy medium: The title reaction of cyclopropenyl carbinols and carbinylamines gives carbo- and heterocycles with a [6.1.0] bicyclic ring fused to an aromatic ring (see scheme, Alloc=allyloxycarbonyl, Boc=tert- butyloxycarbonyl). These reactions are the first examples of the formation of medium-sized rings by the intramolecular cyclopropanation of an alkene with a donor-substituted rhodium carbenoid, which is not generated from a diazo compound.
Oppolzer-type intramolecular Diels-Alder cycloadditions via isomerizations of allenamides
Feltenberger, John B.,Hsung, Richard P.
supporting information; experimental part, p. 3114 - 3117 (2011/08/03)
A new approach to Oppolzer's intramolecular Diels-Alder cycloaddition (IMDA) through γ-isomerization of readily available N-tethered allenamides is described. These IMDA reactions are carried out in tandem with the allenamide isomerization or 1,3-H shift,
