Pd-catalyzed isocyanide insertion/nucleophilic attack by indole C-3/desulfonylation in the same pot: a direct access to indoloquinolines of pharmacological interest

Prasad, B. Raghavendra; Nallapati, Suresh Babu; Kolli, Sunder Kumar; Sharma, Atul Kumar; Yellanki, Swapna; Medisetti, Raghavender; Kulkarni, Pushkar; Shivashankar, Sripelly; Mukkanti, K.; Pal, Manojit

doi:10.1039/c5ra13535d

Cited by 15 publications

(6 citation statements)

References 39 publications

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“…50 As a matter of fact, the unique features of these compounds make them good candidates for being selected for the synthesis of divergent types of heterocycles. [51][52][53][54][55][56][57][58][59][60][61][62][63][64][65][66][67][68][69] Furthermore, their compatibility with domino and cascade reactions, has paved the way for developing novel atom and bond economy synthetic strategies. [70][71][72] Isocyanide is a functional group with outstanding reactivity including the ability to react with both electrophiles and nucleophiles, simultaneously.…”

Section: Introductionmentioning

confidence: 99%

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

2016

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Section: Introductionmentioning

confidence: 99%

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

2016

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“… In this approach, Pd(II) first binds to the pyridinium zwitterion ( 1a ) affording adduct A , which is readily converted to intermediate B via C–H activation. Next, 3,5-diarylimidazo[1,2- a ]pyridine ( 2a ) is obtained by reductive elimination and subsequent desulfonylation, which rearomatizes to drive the overall reaction forward. Finally, in the presence of an excess amount of oxidant, Pd(0) is reoxidized to Pd(II), available for another catalytic cycle.…”

Section: Resultsmentioning

confidence: 99%

3,5-Diarylimidazo[1,2-a]pyridines as Color-Tunable Fluorophores

et al. 2017

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A new protocol for the synthesis of color-tunable fluorescent 3,5-diarylimidazo[1,2-a]pyridines has been achieved via palladium-catalyzed C-H amination of pyridinium zwitterions. Based on experimental results and computational analysis, we extracted a high correlation of photophysical properties with the theoretical concept and predicted emission wavelengths of 3,5-diarylimidazo[1,2-a]pyridines. The emission wavelengths of imidazo[1,2-a]pyridines increase as a function of the electron-withdrawing nature of the substituent on the C5-aryl group of imidazo[1,2-a]pyridine as a result of inductive effects on the LUMO levels. Varying the substituent on the C3-aryl group imidazo[1,2-a]pyridine changes the HOMO levels. Combining these two sites, the HOMO and LUMO levels can be tuned fairly decoupled from each other. This conceptual trend is demonstrated across a series where the C3 and C5 positions were functionalized independently and then utilizes a combination strategy where both sites are used to prepare fluorophores with a large window of emission wavelengths. In view of the biological properties of imidazo[1,2-a]pyridines, the developed method provides an efficient approach for understanding and preparing strongly fluorescent bioprobes.

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“…Another example of the redox-neutral cross-coupling with carbon nucleophiles involves the synthesis of indoloquinolines 31 from 2-(2-iodoarylamino)indoles 29 and isocyanides 30 [ 31 ]. This reaction is postulated to proceed via isocyanide insertion into the generated aryl palladium bond, and subsequent electrophilic aromatic substitution at the highly electron-rich indole C3-position ( Scheme 9 ).…”

Section: Pd 0 -Catalyzed Isocyanide Insertionsmentioning

confidence: 99%

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

et al. 2020

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Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function as a CO-substitute in palladium-catalyzed cross couplings. Over the past decades, isocyanides have emerged as practical and versatile C1 building blocks, whose inherent N-substitution allows for the rapid incorporation of nitrogeneous fragments in a wide variety of products. Recent developments in palladium catalyzed isocyanide insertion reactions have significantly expanded the scope and applicability of these imidoylative cross-couplings. This review highlights the advances made in this field over the past eight years.

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Pd-catalyzed isocyanide insertion/nucleophilic attack by indole C-3/desulfonylation in the same pot: a direct access to indoloquinolines of pharmacological interest

Abstract: A new, simple and straightforward cascade reaction involving the Pd-catalyzed isocyanide insertion followed by a nucleophilic attack by the indole C-3 has been developed. The

Cited by 15 publications

References 39 publications

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

3,5-Diarylimidazo[1,2-a]pyridines as Color-Tunable Fluorophores

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

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