An improved method for the synthesis of stabilized primary enamines and imines

Kloek, James A.; Leschinsky, Kindrick L.

doi:10.1021/jo00401a037

Cited by 36 publications

(9 citation statements)

References 2 publications

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“…In this context, alkylation at the y-C-atom of N-( 1-phenylviny1)-h5-phosphazenes with cr-bromo ketones has been reported,25 in a similar reaction to that described for allylidenephosphorane with halogeno esters 26 and acyl halides.27 However, when h5-phosphazene (1) reacted with methyl iodide at room temperature in chloroform, the crystalline Nmethylaminophosphonium iodide (10) was obtained in a regioselective fashion. The high shift-value of the 31P NMR signal (6, 46.6) and the P-H (3J 8.8 Hz) and P-C (*J 3.4 Hz) coupling constants observed in the 'H and I3C NMR spectra, respectively, for the methyl group are fully consistent l4 with the phosphonium salt structure (10).…”

Section: Phsupporting

confidence: 58%

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Reactivity and selectivity of N-vinylic λ⁵-phosphazenes towards electrophiles. Synthesis of 2-aza-1,3-dienes

Barluenga¹,

Ferrero²,

Palacios³

1990

J. Chem. Soc., Perkin Trans. 1

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The reactivity of the P=N double bond of the N-vinylic h5-phosphazene (1) towards several electrophiles is reported. Intermolecular aza-Wittig reaction of Wphosphazene (1 ) with aldehydes, phenyl isocyanate, and acid anhydrides leads to ethoxycarbonyl 2-aza-l,3-dienes (3), conjugated carbodi-imides (4), and N-protected amino acrylic acid derivatives ( 5 ) , respectively, while the Z-azahexa-l,3,5-triene (8) and also the pyridine (7) are obtained when dienyl h5-phosphazenes (6) are used. Reaction of h5-phosphatene (1) with methyl iodide and acetyl chloride leads t o N-alkylated (10) and N-acylated derivatives (11 ), respectively. Treatment of compound (1 1 ) in the presence of amino derivatives affords 1 -amino-2-azabuta-l,3-dienes (14).

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Section: Phsupporting

confidence: 58%

“…The reaction mixture was stirred for 2 days at room temperature. Evaporation of the solvent at reduced pressure afforded a crude solid, which was recrystallized from hexane-CH,Cl, to yield compound (10)…”

Section: Synthesis Of 4-ethoxycarbonyl-15-diphenyl-13-diazapenta-mentioning

confidence: 99%

Reactivity and selectivity of N-vinylic λ⁵-phosphazenes towards electrophiles. Synthesis of 2-aza-1,3-dienes

Barluenga¹,

Ferrero²,

Palacios³

1990

J. Chem. Soc., Perkin Trans. 1

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“…Ainsi, mis B part quelques rkactions de condensation ou l'une des deux fonctions du dCrivC dicarbonylC n'a qu'un r61e secondaire et reste inchangCe aprks rkaction (7,8), seules sont dCcrites dans la littCrature des condensations de composCs dicarbonylCs avec des bis-iminophosphoranes (9,10). Ce type de rCaction ne fait donc pas apparaitre une rtactivite nouvelle puisque chacune des fonctions iminophosphoranes reagit selon le schCma 1.…”

Section: Introductionunclassified

Nouvelle voie de synthèse d'isoindolones et d'isoquinoléines par condensation d'iminophosphoranes avec l'ortho-phtalaldéhyde: réactions, mécanismes et étude structurale

Aubert¹,

Farnier²,

Guilard³

1990

Can. J. Chem.

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The condensation of various iminophosphoranes with o-phthalaldehyde led directly to N-substituted isoindoline-1-ones and 3-acylisoquinolines. Three different mechanisms, depending on the nature of the iminophosphorane and reaction conditions, are proposed. All the compounds have been fully characterized, particularly by one- and two-dimensional nuclear magnetic resonance spectroscopy. Keywords: isoindolones, isoquinolines, iminophosphoranes.

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“…For these reasons we have developed an alternative route to some α-(fluoroalkyl)-β-sulfinyl enamines 4 (R 2 = Cbz or H and R 1 = R F ) based on an aza-Wittig reaction of imino phosphoranes (Ph 3 PNR 2 , R 2 = Cbz or SiMe 3 ) with fluorinated β-keto sulfoxides 17 (see retrosynthetic scheme, eq 1). A similar methodology had been applied to the synthesis of β-enamino esters. , …”

Section: Introductionmentioning

confidence: 99%

Two Practical and Efficient Approaches to Fluorinated and Nonfluorinated Chiral β-Imino Sulfoxides

Fustero¹,

Navarro²,

Pina³

et al. 1998

J. Org. Chem.

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Reaction of fluorinated and nonfluorinated N-substituted imidoyl chlorides 1 with lithium derivatives of enantiopure methyl p-tolyl sulfoxide 2a (or racemic methyl phenyl sulfoxide 2b) gave a wide variety of chiral N-substituted beta-imino sulfoxides 4 in good to excellent yields. The title compounds (R)-4 were also prepared by aza-Wittig reaction of gamma-fluoro-beta-keto sulfoxides (R)-5 and N-aryl iminophosphoranes 6. The imino-enamino equilibrium was studied, showing, in all instances, the imino form as the predominant tautomer independent of the nature of the N-substituent. The configuration of the C=N double bond was found to be Z for both N-alkyl and N-aryl derivatives on the basis of (1)H NMR NOE difference experiments performed over several compounds. Ab initio calculations (HF/6-31G) carried out on several representative examples of 1 and 4 are, in general, consistent with the experimental results.

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An improved method for the synthesis of stabilized primary enamines and imines

Cited by 36 publications

References 2 publications

Reactivity and selectivity of N-vinylic λ⁵-phosphazenes towards electrophiles. Synthesis of 2-aza-1,3-dienes

Reactivity and selectivity of N-vinylic λ⁵-phosphazenes towards electrophiles. Synthesis of 2-aza-1,3-dienes

Nouvelle voie de synthèse d'isoindolones et d'isoquinoléines par condensation d'iminophosphoranes avec l'ortho-phtalaldéhyde: réactions, mécanismes et étude structurale

Two Practical and Efficient Approaches to Fluorinated and Nonfluorinated Chiral β-Imino Sulfoxides

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An improved method for the synthesis of stabilized primary enamines and imines

Cited by 36 publications

References 2 publications

Reactivity and selectivity of N-vinylic λ5-phosphazenes towards electrophiles. Synthesis of 2-aza-1,3-dienes

Reactivity and selectivity of N-vinylic λ5-phosphazenes towards electrophiles. Synthesis of 2-aza-1,3-dienes

Nouvelle voie de synthèse d'isoindolones et d'isoquinoléines par condensation d'iminophosphoranes avec l'ortho-phtalaldéhyde: réactions, mécanismes et étude structurale

Two Practical and Efficient Approaches to Fluorinated and Nonfluorinated Chiral β-Imino Sulfoxides

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Reactivity and selectivity of N-vinylic λ⁵-phosphazenes towards electrophiles. Synthesis of 2-aza-1,3-dienes

Reactivity and selectivity of N-vinylic λ⁵-phosphazenes towards electrophiles. Synthesis of 2-aza-1,3-dienes