A Convenient Synthesis of 3,5-Disubstituted 2-Acetylindoles

Rajur, Sharanabasava B.; Merwade, A. Y.; Basanagoudar, L. D.

doi:10.1080/00397919208055420

Cited by 18 publications

(5 citation statements)

References 10 publications

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“…Synthesis of the indole-containing fragments was straightforward by using a modification of the protocol that we previously employed. [14] The cyclic heptanoyl indole 9 was generated in a similar manner to that of the acyclic skatoles 6 by using a Japp-Klingemann-Fischer indole synthesis (Scheme 2). [15] These intermediates were then brominated and converted to their corresponding mercaptans by substitution with thioacetate and subsequent hydrolysis to give 8 and 11.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Self‐Association of Double‐Helical AADD Arrays

Mudraboyina

Wisner

2012

Chemistry A European J

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The design and syntheses of four self-complementary oligomers that contain an underlying AADD hydrogen bond sequence are presented, and their self-association was examined in the solution and solid state. The molecular recognition between the two strands is highly sensitive to substitutions of their component heterocycles. Substitution with electron-donating and -withdrawing groups and the influence of preorganization has a large effect on the overall stabilities of the complexes studied. In particular, a wide range (>10(5) M(-1)) of stabilities with respect to substitutions at various positions in the AADD oligomers was demonstrated. In the most extreme case, the dimerization constant measured (K(dimer) ≥4.5×10(7) M(-1)) is comparable to the most stable homodimers of neutral AADD arrays reported to date.

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Section: Resultsmentioning

confidence: 99%

“…Synthesis of the indole‐containing fragments was straightforward by using a modification of the protocol that we previously employed 14. The cyclic heptanoyl indole 9 was generated in a similar manner to that of the acyclic skatoles 6 by using a Japp–Klingemann–Fischer indole synthesis (Scheme ) 15.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Self‐Association of Double‐Helical AADD Arrays

Mudraboyina

Wisner

2012

Chemistry A European J

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“…Synthesis: The synthesis of the DDD hydrogen bonding arrays (Scheme 1) was initiated using a Japp-Klingeman/ Fischer indole approach [17] employing the diazonium salts of anilines containing the desired substituents and either methyl 2-ethylacetoacetate or the one carbon homologue methyl 2-ethyl-3-oxopentanoate to yield 5-substituted acetyl-or propionylskatoles 1 a-d. The 5-cyanoskatoles 2 were obtained by Pd-catalyzed cyanation of the bromides 1 c and 1 d. Acylskatole derivatives 1 and 2 were then a-brominated and the resulting bromides 3 converted to their corresponding mercaptans 4.…”

Section: Resultsmentioning

confidence: 99%

Substituent Effects in Double‐Helical Hydrogen‐Bonded AAA‐DDD Complexes

Wang

Mudraboyina

Wisner

2011

Chemistry A European J

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Two series of DDD and AAA hydrogen-bond arrays were synthesized that form triply-hydrogen-bonded double-helical complexes when combined in CDCl(3) solution. Derivatization of the DDD arrays with electron-withdrawing groups increases the complex association constants by up to a factor of 30 in those arrays examined. Derivatization of the AAA arrays with electron donating substituents reveals a similar magnitude effect on the complex stabilities. The effect of substitution on both types of arrays are modeled quite satisfactorily (R(2) > 0.96 in all cases) as free energy relationships with respect to the sums of their Hammett substituent constants. In all, the complex stabilities can be manipulated over more than three orders of magnitude (>20 kJ mol(-1)) using this type of modification.

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“…When aryldiazonium salts 101 are treated directly with β-ketoesters 102 , deacylation is followed by indole formation to give indole-2-carboxylate esters 106 . Alternatively, if a β-ketoacid 103 is used, decarboxylation occurs and a 2-acylindole 107 is formed . The Japp−Klingemann procedure avoids the formation and use of arylhydrazines, which can be difficult to prepare and handle in some cases.…”

Section: 3 Via Japp−klingemann Reactionmentioning

confidence: 99%

“…37 Alternatively, if a β-ketoacid 103 is used, decarboxylation occurs and a 2-acylindole 107 is formed. 38 The Japp-Klingemann procedure avoids the formation and use of arylhydrazines, which can be difficult to prepare and handle in some cases.…”

Section: Via Japp−klingemann Reactionmentioning

confidence: 99%