Neat synthesis of <i>c</i>-fused pyrroles and its application to macrolactamization

Bera, Anirban; Ali, Sk Asraf; Saha, Amit; Samanta, Shubhankar

doi:10.1080/00397911.2021.1939054

Cited by 4 publications

(5 citation statements)

References 35 publications

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“…DFT studies have been performed to understand the pathway for the formation of the products ( 2 g and 3 g , Scheme 4) and their selectivity with different amine sources (Figure 2). From the experimental observation it has been found that the substrate 1 g furnished 3 g along with minor amount of 2 g in presence of urea (Table 1, entry 7), whereas NH 4 OAc (Table 1, entry 1) or arylamine [12g] gives only fused pyrrole derivatives 2 g or 2 ’’ under neat conditions. The mechanism of these observations can be explained via the nucleophilic attack on the aldehyde of 1 g by the amine to produce the intermediate A (Scheme 4).…”

Section: Resultsmentioning

confidence: 99%

Urea‐Promoted Neat Synthesis of Fused Dihydroisoquinolines and Disubstituted Pyridines: A Mechanistic Observation with Molecular‐Sensing Studies

Azad,

Bera,

Samanta

et al. 2024

Chemistry A European J

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An efficient and short synthesis of fused dihydroisoquinolines, diaryl substituted pyridine derivatives have been established in good to high yields using an environmentally safe, solvent‐metal‐oxidant‐free tandem approach. In this article, we have discussed that the electrocyclic reaction is more pronounced in solid phase in presence of urea whereas the typical aza‐Michael addition is more prominent in presence of arylamine in the solution phase for the substrate 3‐(2‐formylcycloalkenyl)‐acrylic ester derivatives. The wide range of substrate variations and urea‐promoted neat synthesis made our approach more significant in medical and also analytical science. Moreover, the isoquinoline alkaloid Decumbenine B analogue has been synthesized using our newly developed neat methodology. We have also investigated the photophysical properties of the synthesized fused dihydroisoquinoline derivatives. One of the synthesized molecules was used as a sensor for the selective detection of toxic picric acid. Therefore, the effective neat synthesis and molecular sensing applications of these compounds made our approach more exciting in the field of heterocyclic chemistry.

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Section: Resultsmentioning

confidence: 99%

Urea‐Promoted Neat Synthesis of Fused Dihydroisoquinolines and Disubstituted Pyridines: A Mechanistic Observation with Molecular‐Sensing Studies

Azad,

Bera,

Samanta

et al. 2024

Chemistry A European J

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“…Here, we got a broad range of carbocyclic-fused tetracyclic and aromatic-fused pentacyclic lactams but the yield of aryl-fused derivatives was greater than that of the aromatic analog. 27 Scheme 9 Synthesis of crispine A using Baylis Hillman adduct. 24 When the two steps are combined in one-pot under solventfree conditions, then this methodology will be more convenient.…”

Section: Synthesis Of A-fused Pyrrolementioning

confidence: 99%

“…The cyclization was also attempted using several Lewis acids, Scheme 12 Synthesis of 5,8-pyrrole-fused heterocycles via an intramolecular amidation reaction. 27 such as AuCl 3 , FeCl 3 , and Al 2 (SO 4 ) 3 , or the simple organic acid p-TsOH but the yields were only moderate except for Zn(OAc) 2 . One of the structures, 50c, was confirmed by X-ray crystallographic study.…”

Section: Synthesis Of A-fused Pyrrolementioning

confidence: 99%

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Recent synthetic journey on pyrrole-fused compounds

Pramanik¹,

Barik²,

Ali³

et al. 2023

New J. Chem.

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“…In continuation of our research work involving the neat reaction technology, 11 we report here for the first time, a solvent-free rapid synthetic route of isothiazoles 2 via ammonium thiocyanate-promoted single reagent transformation from β-halo vinyl aldehyde 1 . The current protocol reduces the use of volatile solvents, avoids the conventional work-up process and offers an improved green reaction methodology (Scheme 1).…”

Section: Introductionmentioning

confidence: 98%