Gold-Catalyzed Domino Cycloisomerization/Pictet–Spengler Reaction of 2-(4-Aminobut-1-yn-1-yl)anilines with Aldehydes: Synthesis of Tetrahydropyrido[4,3-<i>b</i>]indole Scaffolds

Reddy, B. V. Subba; Swain, Manisha; Reddy, S. Madhusudana; Yadav, J. S.; Sridhar, Balasubramanian

doi:10.1021/jo302068e

Cited by 41 publications

(17 citation statements)

References 48 publications

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“…The authors isolated an intermediate isotryptamine 86 and treated it with AgSbF 6 to assess the role of its excess. The tetrahydropyrido[4,3‐ b ]indole 88 was also obtained, hence concluding that the Ag catalyst facilitates the Pictet–Spengler step 74. In 2009 Liu reported on an Au‐catalyzed green protocol for the preparation of indole‐1‐carboxamides 90 .…”

Section: N‐nucleophilesmentioning

confidence: 92%

“…Reddy and co‐workers reported on a domino cycloisomerization/Pictet–Spengler approach for the production of tetrahydropyrido[4,3‐ b ]indoles 88 74. These compounds were obtained by treatment of ortho ‐alkynylanilines tethered to tosyl amides 84 with 5 mol% IPrAuCl and 10 mol% AgSbF 6 in the presence of benzaldehydes 85 (Scheme ).…”

Section: N‐nucleophilesmentioning

confidence: 99%

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Homogeneous Gold‐Catalyzed Cyclization Reactions of Alkynes with N‐ and S‐Nucleophiles

et al. 2015

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This review covers the formation of N-a nd S-containing heterocycles,i nitiated by gold-catalyzed nucleophilic attack of N-o rS-nucleophiles ontoa lkynes. These typeso fn ucleophiles have been somewhat overlooked as compared to their C-o rO-counterparts in other reviews.I nt his particularw ork, their intramolecular gold-mediated attack ontoa lkynesi sr eviewedi nd epth.I ti ss tructured in such af ashion that the reader will get ac learv iew of which substrates react in which cyclization mode. 1I ntroduction 2N-Nucleophiles 2.Scheme1.endo-a nd exo-dig cyclization modes for heteroatom attack onto Au-activated triple bonds. REVIEWSWouter Debrouwer et al. Scheme 2. Au(I)-catalyzed formationo fp yrroles from homopropargylic azidesb yana cetylenic Schmidt reaction. Scheme3.AuCl 3 -catalyzed preparation of fluorinated pyrroles.Scheme4.Pyrrole synthesis according to Aponick and Akai. REVIEWSHomogeneous Gold-Catalyzed Cyclization Reactions of Alkynes Scheme 32. Formationo fp yrroles via 5-exo-dig cyclization with acationic Au(I) catalyst.Scheme 33. Formationo fhomoallylic pyrroles via aza-Claisen rearrangement according to Gagosz. REVIEWSHomogeneous Gold-Catalyzed Cyclization Reactions of Alkynes Scheme 58. Au-catalyzed hydroamination in the total synthesis of (À)-Quinocarcin.Scheme 59. Reactionb etween o-alkynylbenzaldehydes and anilines under AuCl catalysis.Scheme60. Intramolecular hydroamination and transfer hydrogenation. REVIEWSHomogeneous Gold-Catalyzed Cyclization Reactions of Alkynes Scheme 79. Generation of ac ontact ion pair with retention of stereochemistry,a nd the unobserved sigmatropicr earrangement with inversion of stereochemistry.Scheme 80. Au(III)-catalyzed cycloisomerization with formation of dihydrothiazoles.Scheme81. Au(I)-catalyzed generation of an Au-carbene.

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Section: N‐nucleophilesmentioning

confidence: 92%

Section: N‐nucleophilesmentioning

confidence: 99%

Homogeneous Gold‐Catalyzed Cyclization Reactions of Alkynes with N‐ and S‐Nucleophiles

et al. 2015

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“…In a reaction defined "iso-Pictet-Spengler", chiral thioureas TH-2, TH-3, or TH-4 (20 mol%) (see Scheme 81) and benzoic acid PhCO 2 H (10-20 mol%) were found as the more effective cocatalysts and gave the THGC 261a (X = H, R = i-Pr; R = H) with a 97% yield and 95% ee. [275]. Ketone substrates I were also successfully applied to the iso-P-S protocol.…”

Section: Iso-pictet-spenglermentioning

confidence: 99%

The Pictet-Spengler Reaction Updates Its Habits

et al. 2020

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The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and variable synthetic method for the construction of privileged pharmacophores such as tetrahydro-isoquinolines (THIQs), tetrahydro-β-carbolines (THBCs), and polyheterocyclic frameworks. In the lustro (five-year period) following its centenary birthday, the P-S reaction did not exit the stage but it came up again on limelight with new features. This review focuses on the interesting results achieved in this period (2011–2015), analyzing the versatility of this reaction. Classic P-S was reported in the total synthesis of complex alkaloids, in combination with chiral catalysts as well as for the generation of libraries of compounds in medicinal chemistry. The P-S has been used also in tandem reactions, with the sequences including ring closing metathesis, isomerization, Michael addition, and Gold- or Brønsted acid-catalyzed N-acyliminium cyclization. Moreover, the combination of P-S reaction with Ugi multicomponent reaction has been exploited for the construction of highly complex polycyclic architectures in few steps and high yields. The P-S reaction has also been successfully employed in solid-phase synthesis, affording products with different structures, including peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the enzymatic version of P-S has been reported for biosynthesis, biotransformations, and bioconjugations.

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“…Multicomponent [32][33][34][35][36][37] and domino [38,39] reactions are powerful tools in the modern drug discovery process in terms of lead finding and lead optimization.…”

Section: Introductionmentioning

confidence: 99%

An Efficient One‐Pot Four‐Component Synthesis of Some New Spirooxindole Dihydropyridine Using Alum as a Heterogeneous Green Catalyst

Mohammadi

Taheri

Amouzegar

2016

Journal of Heterocyclic Chem

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4‐Nitro‐2,3‐dihydrospiro[imidazo[1,2‐a]indeno[2,1‐e]pyridine‐5,3′‐indoline]‐2′,6(1H)‐dione derivatives have been synthesized in good yields in a one‐pot four‐component, and efficient process by reaction of corresponding isatins, 1,3‐indandione, diamine, and nitro ketene dithioacetal in the presence of KAl(SO4)2.12H2O (Alum) as a nontoxic and easily available heterogeneous green catalyst.

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Gold-Catalyzed Domino Cycloisomerization/Pictet–Spengler Reaction of 2-(4-Aminobut-1-yn-1-yl)anilines with Aldehydes: Synthesis of Tetrahydropyrido[4,3-b]indole Scaffolds

Cited by 41 publications

References 48 publications

Homogeneous Gold‐Catalyzed Cyclization Reactions of Alkynes with N‐ and S‐Nucleophiles

Homogeneous Gold‐Catalyzed Cyclization Reactions of Alkynes with N‐ and S‐Nucleophiles

The Pictet-Spengler Reaction Updates Its Habits

An Efficient One‐Pot Four‐Component Synthesis of Some New Spirooxindole Dihydropyridine Using Alum as a Heterogeneous Green Catalyst

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