New Syntheses of Isochromene

Cottet, F.; Cottier, Louis; Descotes, G.

doi:10.1055/s-1987-27982

Cited by 30 publications

(32 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…However, a high cost of the production of HMF is the most troublesome. Let me be allowed to quote Cottier and Descotes' remark concluding their article 6 entitled "5-Hydroxyemthylfurfural syntheses and chemical transformations". They said there: "...With a more competitive price, HMF should offer new development in diversified fields..." and it is true, because costs, which should be covered just for obtaining HMF limit greatly the progress of studies on this interesting and promising compound.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Chemistry and Applications of 5‐Hydroxymethyl‐furfural and Its Derivatives

Lewkowski

2003

ChemInform

118

View full text Add to dashboard Cite

show abstract

Section: Discussionmentioning

confidence: 99%

“…This would result in a cross-polymerisation. Despite, glucose is still utilised in industry for the preparation of HMF because of its price lower than fructose 6 .…”

Section: The Kinetics Of the Hmf Synthesismentioning

confidence: 99%

Synthesis, Chemistry and Applications of 5‐Hydroxymethyl‐furfural and Its Derivatives

Lewkowski

2003

ChemInform

118

View full text Add to dashboard Cite

show abstract

“…First syntheses of HMF were catalysed by oxalic acid 7,8,12,15 and till now nearly one hundred inorganic and organic compounds were positively qualified as catalysts for the HMF synthesis. Cottier 6 divided catalysts into five groups; they are collected in Table 1.…”

Section: The Kinetics Of the Hmf Synthesismentioning

confidence: 99%

Synthesis, chemistry and applications of 5-hydroxymethyl-furfural and its derivatives

Lewkowski¹

2001

Arkivoc

414

144

View full text Add to dashboard Cite

“…Sous azote et a l'abri de la lumikre, on melange 0,s g (2,7 mmol) de chlorhydrine 9 avec 6,s mL de pyridine anhydre, 16 For personal use only.…”

Section: Synthpse De L'ace'toxy-3-chloro-4-isochromanne 11unclassified

Photocyclisations de cétoacétals aromatiques en vue d'une approche synthétique de la crombénine

Cottet¹,

Cottier²,

Descotes³

1990

Can. J. Chem.

View full text Add to dashboard Cite

La crombCnine 1 est un spiropeltogynoi'de prksentant une structure spiroacCtalique. Une approche de sa synthkse a t t t entreprise a partir d'orthocarbonylphCnoxyisochromanne avec pour Ctape clef une rCaction de photocyclisation de type Nonish II. En sCrie isochromannique, le cycle aromatique induit une reaction secondaire de cyclisation sur le radical benzylique compCtitive avec la reaction de spirocyclisation. Cependant, la presence de substituant Clectroattracteur ou encombrant en C-4' diminue la formation du dCrivC bicyclique de type [4.3.1] et oriente la photolyse vers le produit de structure spirannique.Mots cle's : acCtals, isochromkne, photocyclisation, spiroacCtals.FRAN~OISE COTTET, LOUIS COTTIER and GBRARD DESCOTES. Can. J. Chem. 68, 1251Chem. 68, (1990.Crombenin 1 is a spiropeltogynoid compound with a spiroacetal moiety. A similar structure was synthesized starting from an orthocarbonylphenoxyisochroman by a Norrish type I1 photocyclisation. With an isochroman compound, the aromatic ring induces benzyl radical formation to give chiefly a bicyclic [4.3.1] derivative. However, with the introduction of electron-withdrawing or bulky substituents at C-4 ', this side reaction is limited and the spiranic product becomes preponderant.Key words: acetals, isochroman, photocyclisation, spiroacetals.La crombenine 1 (R = OH) (1, 2) est une substance isolte en trbs faible quantitt de 1'ccAcacia crombein. Sa structure, identifike 2 partir de l'un de ses dtrivts tttra-O-mtthylt 1 (R = OMe) (3), possbde un motif spiroacttalique (figure 1) present dans de nombreuses substances biologiquement actives (4-8). Ayant ttudit difftrentes reactions de spirocyclisation par voie photochimique de systbmes cttoacttaliques, une approche de la synthkse de la crombknine a t t t entreprise ayant pour ttape clef une rtaction de photocyclisation de type Nonish 11.En effet, les rtsultats obtenus en skrie glycosidique (9, 10) et en strie tttrahydropyrannique (1 1-13) permettent d'envisager la synthbse de la crombtnine ou de ses analogues selon un schkma rktrosynthttique en quatre ttapes (Schtma 1). La condensation d'un phtnol orthocarbonylt A avec un isochrombne B ou un dtrivt, devrait donner un acttal C qui, par photolyse, serait transform6 en produit spirannique D. Selon la nature de la fonction hydroxyle sur le cycle furannique, une simple oxydation ou une dtshydratation suivie d'une oxydation conduirait au compost E posstdant la fonction cttone souhaitke. Ainsi, compte tenu des rtsultats obtenus avec les phtnylglucosides orthocarbonylts (9), cette stquence rtactionnelle a d'abord ett ttudite en strie tktrahydropyrannique puis elle a t t t ttendue B des substrats isochromanniques. Resultats SynthPse des ace'talsLa fonction aldthydique a ttk choisie comme groupe chromophore, car elle auraifpermis d'acctder a un alcool secondaire en C-3 directement oxydable. La condensation directe entre l'aldthyde salicylique et le dihydropyranne n'ayant pu Ctre rtaliste, le tttrahydropyrannyloxy-2 benzaldthyde 6 a kt6 synthttist B partir de l'alcool ...

show abstract

New Syntheses of Isochromene

Cited by 30 publications

References 0 publications

Synthesis, Chemistry and Applications of 5‐Hydroxymethyl‐furfural and Its Derivatives

Synthesis, Chemistry and Applications of 5‐Hydroxymethyl‐furfural and Its Derivatives

Synthesis, chemistry and applications of 5-hydroxymethyl-furfural and its derivatives

Photocyclisations de cétoacétals aromatiques en vue d'une approche synthétique de la crombénine

Contact Info

Product

Resources

About