Journal ArticleDOI
Investigations on regio- and stereoselectivities in cycloadditions involving α- (3-pyridyl)-N-phenylnitrone: Development of an efficient route to novel nicotine analogs
TLDR
In this paper, a mechanistic rationalization of the obtained results in terms of electronic, steric and secondary interactions is proffered, and a loss of regioselectivity is observed with methyl vinyl ketone and methyl acrylate, due to intervention of HOMO-dipole-LUMO-Dipolarophile interaction.About:
This article is published in Journal of Heterocyclic Chemistry.The article was published on 2005-09-01. It has received 15 citations till now. The article focuses on the topics: Nitrone & Regioselectivity.read more
Citations
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Journal ArticleDOI
PASS assisted prediction and pharmacological evaluation of novel nicotinic analogs for nootropic activity in mice
TL;DR: The study showed that these compounds are true nicotine analogs with desirable efficacy and safety profile for their use as effective nootropic agents.
Journal ArticleDOI
Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines
TL;DR: In this article, the microwave assisted neat synthesis of α-phenyl- tert -butylnitrone (PBN) and other alkyl and aryl nitrones and also the rapid synthesis of isoxazolidines resulting from 1,3-dipolar cycloaddition of nitrones to ethyl trans -crotonate.
Journal ArticleDOI
Investigations on synthesis of indole based constrained mimetic scaffolds through 1,3-dipolar cycloadditions of the C-(3-indolyl)-N-phenylnitrone with a variety of olefinic and allenic dipolarophiles under microwave irradiation
Surinderjit Singh Bhella,Ajay Pal Singh Pannu,M. Elango,Ashish Kapoor,Maninder Singh Hundal,Mohan Paul S. Ishar +5 more
TL;DR: In this article, a 1,3-dipolar cycloadduct of C-(3-indolyl)-N-phenylnitrone with a number of olefinic dipolarophiles was analyzed in terms of HOMO-dipole-LUMOdipolarophile and involved secondary orbital/steric interactions in the transition states intervening these cycloadditions.
Journal ArticleDOI
Regio- and stereoselective synthesis of novel isoxazolidine heterocycles by 1,3-dipolar cycloaddition between C-phenyl-N-methylnitrone and substituted alkenes. Experimental and DFT investigation of selectivity and mechanism
Djamila Hellel,Fouad Chafaa,Abdelmalek Khorief Nacereddine,Abdelhafid Djerourou,Emmanuel Vrancken +4 more
TL;DR: In this paper, a series of isoxazolidine heterocycles was synthesized through the 1,3-dipolar cycloaddition (13DC) reaction of C-phenyl-N-methylnitrone with different substituted alkenes.
Journal ArticleDOI
Synthesis and cytotoxic evaluation of substituted 3-(3′-indolyl-/3′-pyridyl)-isoxazolidines and bis-indoles
Vishal Sharma,Raman Kalia,Tilak Raj,Vivek K. Gupta,Nitasha Suri,Ajit Kumar Saxena,Deepak Sharma,Surinderjit Singh Bhella,Gurpinder Singh,Mohan Paul S. Ishar +9 more
TL;DR: In this article, a stereoselective 1,3-dipolar cycloadditions of C -(3-indolyl)- N -phenylnitrone (10) with different mono-substituted, disubstitized and cyclic dipolarophiles under mono-mode microwave irradiation were carried out to obtain substituted 3-(indol-3′-3-yl)- N-phenyl-isoxazolidines (16−22).
References
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Journal ArticleDOI
Asymmetric 1,3-Dipolar Cycloaddition Reactions
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Kinetics and Mechanism of 1,3-Dipolar Cycloadditions
TL;DR: Criteria for the mechanism of 1,3-dipolar cycloadditions which lead to 5-membered rings are provided by the stereoselectivity observed with cis-trans isomeric dipolarophiles, by the effect of solvent and substituents on the rate constants, and by orientation phenomena.
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Origin of reactivity, regioselectivity, and periselectivity in 1,3-dipolar cycloadditions
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Epibatidine: a novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an ecuadoran poison frog
Thomas F. Spande,H. M. Garraffo,M. W. Edwards,Herman J. C. Yeh,Lewis K. Pannell,John W. Daly +5 more
TL;DR: A potent non-opioid analgesic, epibatidine, has been isolated from skins of the Ecuadoran poison frog, Epipedobates tricolor, and its structure determined by MS, IR, and 1 H NMR analyses as exo-2-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane represents a unique new class of alkaloids.