Phasentransfer-katalysierte<i>N</i>-Acylierung von Indol

Illi, V.

doi:10.1055/s-1979-28695

Cited by 53 publications

(13 citation statements)

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“…Synthesis of N-H meridianin analogues. Following the protocol (see Scheme 1), indole precursors 1 [16,17] were tosylated using a previously reported phase transfer reaction [18] to give N-tosylindoles 2 in very good yields (87-95%). We found this protocol more convenient than sodium hydride anion formation and tosylation (see Fresneda 2001) [12].…”

Section: Resultsmentioning

confidence: 99%

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Towards the Syntheses of N—H and N‐Alkylated Derivatives of Meridianins.

Simon¹,

Couthon‐Gourvès²,

Haelters³

et al. 2007

ChemInform

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Section: Resultsmentioning

confidence: 99%

“…General procedure for analogues (6) and derivatives (17)(18)(19)(20)(21). To a solution of 4 (2.9 mmol) and guanidine hydrochloride (0.35 g, 3.6 mmol) in refluxing ethanol (5 mL) was added a solution of sodium (0.13 g, 5.8 mmol) in ethanol (10 mL).…”

Section: General Procedures Formentioning

confidence: 99%

Towards the Syntheses of N—H and N‐Alkylated Derivatives of Meridianins.

Simon¹,

Couthon‐Gourvès²,

Haelters³

et al. 2007

ChemInform

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“…General procedure for synthesis of heterocyclic carboxamides : All the heterocyclic amides were synthesized according to ref. 47 The acyl chloride (15 mmol) was slowly added over 20 min with mechanical stirring to a slurry of the heterocyclic compound (10 mmol) and finely powdered sodium hydroxide (1 g) in dry dichloromethane (30 mL) containing Aliquat 337 (40 mg). The mixture was then extracted with 1 % aqueous ammonium chloride and water.…”

Section: Methodsmentioning

confidence: 99%

A Catalytic Antibody Programmed for Torsional Activation of Amide Bond Hydrolysis

Aggarwal

Benedetti

Berti

et al. 2003

Chemistry A European J

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Amidase antibody 312d6, obtained against the sulfonamide hapten 4 a that mimics the transition state for hydrolysis of a distorted amide, accelerates the hydrolysis of the corresponding amides 1 a-3 a by a factor of 10(3) at pH 8. The mechanisms of both the uncatalyzed and antibody-catalyzed reactions were studied. Between pH 8 and 12 the uncatalyzed hydrolysis of N-toluoylindoles 1 a and 3 a shows a simple first-order dependence on [OH(-)], while hydrolysis of 3 a is zeroth-order in [OH(-)] below pH 8. The pH profile for hydrolysis of the corresponding tryptophan amide 2 a is more complex due to the dissociation of the zwitterion into an anion with pK(a) 9.74; hydrolysis of the zwitterionic and the anionic form of 2 a both show simple first-order dependence on [OH(-)]. Absence of (18)O exchange between H(2) (18)O/(18)OH(-) and the substrate, a normal SKIE for both 1 a (k(H)/k(D)=1.12) and 3 a (k(H)/k(D)=1.24) and the value of the Hammett constant rho for hydrolysis of p-substituted amides 3 a-e are consistent with an ester-like mechanism in which formation of the tetrahedral intermediate is rate-determining and the amine departs as anion. The 312d6-catalyzed hydrolysis of 3 a was studied between pH 7.5 and 9, and its independence of pH in this range indicates that water is the reacting nucleophile. Hydrolysis of 3 a is only partially inhibited by the sulfonamide hapten, and this indicates that non-specific catalysis by the protein accompanies the specific process. Only the nonspecific process is observed in the hydrolysis of amides 3 with para substituents other than methyl. Binding studies on the corresponding series of p-substituted sulfonamides 5 a-e confirm the high specificity of antibody 312d6 for p-methyl substituted substrates.

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“…Scheme 1 depicts Bowman's approach which was carried out with a few modifications as described in the EXPERIMENTAL. Uhle's ketone (6) 4 was protected as N-tosyl derivative using the combination of Illi 5 and Kikugawa's procedure 6 for N-sulfonylation of indoles. The N-protected ketone (7) 7 was treated with bromine-1,4-dioxane to yield α-bromo ketone (8).…”

Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

Chemistry of Indoles Carrying a Basic Function. Part IX. Unexpected Cyclizations of Diketones Derived from Uhle’s Ketone

et al. 2004

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Starting from a tricyclic diketone (14) obtained by Bowman's method, a tetracyclic oxonaphthalene derivative (17) has been prepared through intramolecular aldol condensation followed by indole → naphthalene isomerization. An unexpected formation of a lactol ether (16) was observed as a result of acidic treatment of 14. Two modified reaction sequences starting from Nmethyl derivatives have also been presented. The keto ketal (26) gave a macrocyclic lactol (27) with unexpected structure as a result of deketalization with trimethylsilyl iodide. The formation of a tetracyclic lactam (37) was observed while applying the modified Reformatsky reaction to ketone (33). About two decades after the first successful synthesis of racemic lysergic acid (1; Figure 1) by the Woodward-Kornfeld group, 2 Bowman and co-workers tried to adopt the key elements of the results of this legendary American cooperation. Their experiments 3 supplied two instructive facts. While the 4bromo derivative of the so-called Kornfeld's ketone (2) reacts smoothly with methylaminoacetone ethylene ketal (3) yielding a tertiary amine (4, 71 %), 2 the corresponding indole derivative (e.g. 1-acetyl-4-bromo-Uhle ketone; 5) did not afford any basic material using the same reaction conditions. 3d 14 O N Ts N CO 2 Me Me Scheme 1-reagents and conditions: a) KOH/TsCl, TBAHS, CH 2 Cl 2 , 0 o C rt, 1.5 h, 91 %; b) Br 2-1,4-dioxane, CCl 4 +CHCl 3 +Et 2 O,

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Phasentransfer-katalysierteN-Acylierung von Indol

Cited by 53 publications

References 0 publications

Towards the Syntheses of N—H and N‐Alkylated Derivatives of Meridianins.

Towards the Syntheses of N—H and N‐Alkylated Derivatives of Meridianins.

A Catalytic Antibody Programmed for Torsional Activation of Amide Bond Hydrolysis

Chemistry of Indoles Carrying a Basic Function. Part IX. Unexpected Cyclizations of Diketones Derived from Uhle’s Ketone

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