Direct N-vinylation of aryl and hetaryl carboxamides with trimethoxyvinylsilane

Arsenyan, Pavel; Petrenko, Alla; Belyakov, Sergey

doi:10.1016/j.tetlet.2008.06.117

Cited by 18 publications

(7 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For the synthesis of the starting material, 2thiophenecarbonyl chloride, see: Kruse et al (1989). For related structures, see: Arsenyan et al (2008); Elshaarawy & Janiak (2011); Low et al (2009).…”

Section: Related Literaturementioning

confidence: 99%

See 1 more Smart Citation

Thiophene-2-carbonyl azide

et al. 2013

View full text Add to dashboard Cite

The title compound, C5H3N3OS, is almost planar (r.m.s. deviation for the ten non-H atoms = 0.018 Å) and forms an extended layer structure in the (100) plane, held together via hydrogen-bonding interactions between adjacent molecules. Of particular note is the occurrence of RC—H⋯N−=N+=NR interactions between an aromatic C—H group and an azide moiety which, in conjunction with a complementary C—H⋯O=C interaction, forms a nine-membered ring.

show abstract

Section: Related Literaturementioning

confidence: 99%

“…(2013). E69, o1298 (Arsenyan et al, 2008;Elshaarawy & Janiak, 2011;Low et al, 2009) are, in contrast, dominated by N-H•••O/N hydrogen bonding, resulting in two different one-dimensional chains (Arsenyan et al, 2008;Low et al, 2009), and a two-dimensional sheet (Elshaarawy & Janiak, 2011).…”

Section: Sup-1mentioning

confidence: 99%

Thiophene-2-carbonyl azide

et al. 2013

View full text Add to dashboard Cite

show abstract

“…For the synthesis of the title compound, see: Binder et al (1977); Kruse et al (1989). For related structures, see: Arsenyan et al (2008); Elshaarawy & Janiak (2011); Low et al (2009); Hsu et al (2013).…”

Section: Related Literaturementioning

confidence: 99%

tert-ButylN-(thiophen-2-yl)carbamate

Hsu¹,

Singer²,

Cordes³

et al. 2013

Acta Cryst E

View full text Add to dashboard Cite

In the title compound, C9H13NO2S, the dihedral angle between the thiophene ring and the carbamate group is 15.79 (14)°. In the crystal structure, intramolecular C—H⋯O interactions in tandem with the tert-butyl groups render the packing of adjacent molecules in the [001] direction nearly perpendicular [the angle between adjacent thiophene rings is 74.83 (7)°]. An intermolecular N—H⋯O hydrogen bond gives rise to a chain extending along [001]. The crystal studied was found to be a racemic twin.

show abstract

“…[3] N-Vinyl amide polymer variants have not yet been widely explored owing to the lack of convenient general methods to access the monomer feedstocks (Scheme 1). [4][5][6] Given the utility of these compounds,itissurprising that methods to access N-vinyl amides remain relatively scarce.W er eport herein an ovel method involving the generation of avinyl azide in situ for the direct synthesis of N-vinyl amides from a-substituted aldehydes and, remarkably, a,b-unsaturated N-vinyl amides from a-substituted esters.The application of substituted vinyl azides to the synthesis of amides and heterocycles has attracted consid-erable attention as an important and versatile emerging technology. [7] Azide-enolate cycloaddition reactions are known, and have recently found increasing application in triazole synthesis.…”

mentioning

confidence: 99%

Unexpected Direct Synthesis of N‐Vinyl Amides through Vinyl Azide–Enolate [3+2] Cycloaddition

et al. 2017

View full text Add to dashboard Cite

The unexpected synthesis of industrially important N-vinyl amides directly from aldehydes and a,b-unsaturated N-vinyl amides from esters is reported. This reaction probably proceeds through an initial [3+ +2] azide-enolate cycloaddition involving av inyl azide generated in situ. As urvey of the reaction scope and preliminary mechanistic findings supported by quantum computational analysis are reported, with implications for the future development of atom-efficient amide synthesis.I ntriguingly,t his study suggests that (cautious) reevaluation of azidoethene as as ynthetic reagent may be warranted. Scheme 2. Azide-enolate [3+ +2] cycloaddition reactions implicated in amide and triazoline synthesis. LDA = lithium diisopropylamide, LHMDS = lithium hexamethyldisilazide. Scheme 1. Industrially important N-vinyl amides 1 and 2. [3a]

show abstract

Direct N-vinylation of aryl and hetaryl carboxamides with trimethoxyvinylsilane

Cited by 18 publications

References 13 publications

Thiophene-2-carbonyl azide

Thiophene-2-carbonyl azide

tert-ButylN-(thiophen-2-yl)carbamate

Unexpected Direct Synthesis of N‐Vinyl Amides through Vinyl Azide–Enolate [3+2] Cycloaddition

Contact Info

Product

Resources

About