96293-28-6

Upstream product

• 21889-88-3 hept-6-en-2-one 
• 505-03-3 5-oxohexanal 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 19726-39-7 methyl diethylphosphorylacetate 

Downstream Products

• 1257107-93-9 (2E,7E)-methyl 7-(2-(4-chlorophenyl)hydrazono)oct-2-enoate 
• 1257108-01-2 (E)-methyl 7-chloro-7-((E)-(4-chlorophenyl)diazenyl)oct-2-enoate 
• 130739-49-0 (E)-7-[(E)-(R)-1-Phenyl-ethylimino]-oct-2-enoic acid methyl ester 

Relevant academic research and scientific papers

Intramolecular 1,3-dipolar cycloadditions of dihydroimidazolium ylides: Synthesis of pyrrolo[1,2,3-de]quinoxalines and imidazo[1,2-a]indoles

N-Alkylation of 4,5-dihydroimidazoles with alkene-containing bromomethyl ketones and treatment of the so-formed 4,5-dihydroimidazolium ions with DBU gives rise to an intramolecular 1,3-dipolar cycloaddition reaction that affords (via a reaction cascade involving eliminative ring-opening, recyclisation and prototropic tautomerism) unexpected hexahydropyrrolo[1,2,3-de]quinoxaline products. Steric bulk in both the dihydroimidazole and the dipolarophile allows isolation of an imidazo[1,2-a]indole, the initial product of cycloaddition. When the bromomethyl ketone contains no other functionality, or when cycloaddition is inhibited due to steric constraints, the dihydroimidazolium ion undergoes ring-opening hydrolysis followed by recyclization of the exposed amino ketone to afford either 3-alkyl-1-formylpiperazine-2-ones or 3-aryl-1-formyl-1,4,5,6- tetrahydropyrazines. The Royal Society of Chemistry 2006.

Pyrrolo[1,2,3-de]quinoxalines: Unexpected products from 1,3-dipolar cycloaddition of dihydroimidazolium ylides

4,5-Dihydroimidazoles undergo an N-alkylation and 1,3-dipolar cycloaddition cascade with unsaturated α-bromoketones, with subsequent eliminative ring-opening, recyclisation and tautomerisation to form unexpected hexahydropyrrolo[1,2,3-de]quinoxalines.

Syntheses of α,β-unsaturated carbonyl compounds from the reactions of monosubstituted ozonides with stable phosphonium ylides

Ozonides derived from terminal alkenes reacted with 1.3 mol equiv. of stable phosphonium ylides to give (E)-αβ-unsaturated carbonyl compounds in good to excellent yields. No reducing agent is needed in the reaction. However, alkoxyalkyl-substituted ozonides afforded a mixture of (Z)- and (E)-αβ-unsaturated carbonyl compounds under similar condition. The E/Z isomeric ratio is affected by the position of the heteroatom in the substituent of the ozonides. The possible mechanism of this reaction will be discussed. (C) 2000 Elsevier Science Ltd.

Intramolecular Michael addition of N- and O-centred nucleophiles to tethered acrylates. The role of double-bond geometry in controlling the diastereoselectivity of cyclizations teading to 2,6-disubstituted tetrahydropyrans and piperidines

The oxyanion derived from hydroxyacrylate E-(5) undergoes smooth intramolecular Michael addition to give the trans-2,6-disubstituted tetrahydropyran (7) as the major product of reaction. In contrast, the oxyanion obtained from isomer Z-(5) cyclizes to give the cis-2,6-disubstituted tetrahydropyran (6) as the major product. Such chemistry has been extended to the enantioselective synthesis of (+)-(6) the acquisition of which constitutes a formal total synthesis of acid (+)-(2), a constituent of the glandular secretion from the civet cat (Viverra civetta). Reductive amination of keto acrylate (12) affords an intermediate amine which cyclizes, in situ, to give the cis-2,6-disubstituted piperidine (26). Analogous treatment of compound (13) delivers the isomeric trans-2,6-disubstituted piperidine (27) as the exclusive product of reaction. Transition state structures have been proposed to account for the diastereoselectivities observed in all of the cyclization reactions.

X = Y - ZH systems as potential 1,3-dipoles part 35. Generation of nitrones from oximes. Class 3 processes. Tandem intramolecular Michael addition (1,3-azaprotio cyclotransfer) - Intermolecular 1,3-dipolar cycloaddition reactions

Aldoximes and ketoximes possessing γ- or δ-alkenyl substituents undergo thermal conversion to 5-and 6- membered cyclic nitrones via a 1,3-azaprotio cyclotransfer, a 2n + 2oσ + 2π concerted process, rather than a Michael addition. The reactions can be performed as a tandem nitrone formation-cycloaddition sequence or, if required, the intermediate nitrones can be isolated. The cycloadditions usually proceed via an exo-transition state and show both regio- and diastereofacial-specificity. Preliminary attempts at chiral induction via a menthyl auxiliary are reported.

The Reaction of Ozonides from Mono-substituted Alkenes with Stabilized Phosphorus Ylides

Ozonides derived from mono-substituted alkenes react with methyl (triphenylphosphoranylidene)acetate or (triphenylphosphoranylidene)acetophenone to form trans-α,β-unsaturated esters or ketones, respectively, in high yields.