Acyl cyanides as carbonyl heterodienophiles

Connors, Richard; Durst, Tony

doi:10.1016/s0040-4039(00)60164-8

Cited by 13 publications

(4 citation statements)

References 10 publications

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“…Reaction of 64 with phenyltriazolinedione (PTD) and other dienophiles all occur at the less hindered face of the diene system, terminating at the R,R′-positions of the oQDM. 84 An effective route to R-hydroxy-oQDMs is the well established 37,85,86 photoenolization of o-alkylbenzaldehydes and related carbonyl compounds (61) by a photochemical 1,5-hydrogen shift. The mechanism of this photoenolization is now very well understood, and many of the generated intermediates have been observed and characterized via time-resolved spectroscopy.…”

Section: B Photochemical Generation Of Substituted Carbocyclic O-quin...mentioning

confidence: 99%

“…An effective route to α-hydroxy-oQDMs is the well established ,, photoenolization of o -alkylbenzaldehydes and related carbonyl compounds ( 61 ) by a photochemical 1,5-hydrogen shift. The mechanism of this photoenolization is now very well understood, and many of the generated intermediates have been observed and characterized via time-resolved spectroscopy .…”

Section: B Photochemical Generation Of Substituted Carbocyclic O-quin...mentioning

confidence: 99%

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o-Quinodimethanes: Efficient Intermediates in Organic Synthesis

1999

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Section: B Photochemical Generation Of Substituted Carbocyclic O-quin...mentioning

confidence: 99%

Section: B Photochemical Generation Of Substituted Carbocyclic O-quin...mentioning

confidence: 99%

o-Quinodimethanes: Efficient Intermediates in Organic Synthesis

1999

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“…20 Acyl cyanides are also reactive toward photochemically generated o-quinodimethanes 21 and act as substrates in the Paterno-Büchi reaction with furan. 22 In addition, AcCN is useful for the preparation of optically pure 1-cyanovinyl esters which serve as dienophilic equivalents of Ketene in [4 + 2] …”

Section: Cycloadditionsmentioning

confidence: 99%

Acetyl Cyanide

Morris¹

2001

Encyclopedia of Reagents for Organic Synthesis

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“…Our report (7) of the cycloaddition of both thermally and photochemically generated o-quinodimethanes with benzoyl and acetyl cyanide (see Scheme 2), represents the first example in which an acyl cyanide acts in such a capacity. The recent publication by Kessar et al which describes the synthesis of various 3-aryl-3,4-dihydroisocoumarins and protoberberines involving fluorodesilylation of 2-((trimethylsily1)-methyl) benzoyl chlorides, 1, in the presence of aromatic aldehydes and 3,4-dihydroisoquinolium salts (8), is closely related to our work.…”

Section: Introductionmentioning

confidence: 96%

Acyl cyanides as carbonyl heterodienophiles: application to the synthesis of naphthols, isoquinolones, and isocoumarins

Connors¹,

Tran²,

Durst³

1996

Can. J. Chem.

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Irradiation of 2-methylbenzoyl cyanide (3a) in acetonitrile solution results in the formation of its dimer, which upon loss of HCN gives rise to the cycloadduct 7a. The dimerization also proceeds efficiently with derivatives of 3a giving adducts 7b and 7c. When 2-methylaroyl cyanides are photolyzed in the presence of a more reactive acyl cyanide the mixed adducts 8a-e are obtained in excellent yields. The cycloadducts 70-c and 80-e react with carbon and nitrogen nucleophiles by a tandem addition-cyclization sequence furnishing substituted naphthols (IOU and lob) and isoquinolones (lla-d), respectively. Isocoumarins 12a and 12b were prepared from the adducts 8a and 8e by treatment with potassium tert-butoxide in THF.Key words: naphthols, isoquinolones, isocoumarins, synthesis of; acyl cyanides; hetero Diels-Alder.Resume : L'irradiation du cyanure de 2-mtthylbenzoyle (3a) en solution dans l'acttonitrile conduit 5 la formation de son dimkre qui, par perte de HCN, fournit le cycloadduit 7a. La dimerisation se produit aussi d'une faqon efficace avec les dtrivts du compost 30; elle conduit alors aux composts 70 et 7c. Lorsqu'on effectue la photolyse des cyanures de 2-mtthylaroyle en prtsence d'un cyanure d'acyle plus rtactif, on obtient alors les produits mixtes 8u-e avec d'excellents rendements. Les cycloadduits 7u-c et 8a-e rtagissent avec les nucltophiles carbones et azotts par une sequence de rtactions d'additioncyclisation en tandem qui fournissent respectivement des naphtols (10a et lob) et des isoquinoltines (lla-d) substituts. Par reaction des adduits 8a et 8e avec du ferf-butylate de potassium dans le THF, on a prepart les isocoumarines 120 et 120.

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Acyl cyanides as carbonyl heterodienophiles

Cited by 13 publications

References 10 publications

o-Quinodimethanes: Efficient Intermediates in Organic Synthesis

o-Quinodimethanes: Efficient Intermediates in Organic Synthesis

Acetyl Cyanide

Acyl cyanides as carbonyl heterodienophiles: application to the synthesis of naphthols, isoquinolones, and isocoumarins

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