InCl3-catalyzed efficient synthesis of spiro-perimidine derivatives

Yasaei, Zahra; Mirzaei, Peiman; Bazgir, Ayoob

doi:10.1016/j.crci.2010.02.002

Cited by 17 publications

(9 citation statements)

References 38 publications

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“…The 1 H and 13 C-NMR spectra of spiro- N,N -ketal 6 showed good agreement with those reported for 1',3'-dispiro[indoline-3,2'-perimidin]-2-one [22]. Compound 7 was identified as quinazolino[3,4-a]perimidin-6(5 H )-one on the basis of X-ray analysis results (Figure 3), and its spectral data were identical to those reported in the literature [24].…”

Section: Resultssupporting

confidence: 82%

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Novel Rearrangements in the Reactions Directed Toward Preparation of Spiro-N,N-ketals: Reactions of Naphthalene-1,8-diamine with Ninhydrin and Isatin

et al. 2012

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Spiro-N,N-ketal 5, consisting of a phthaloperine heterocyclic ring and a naphtha[1,8-ef][1,4]diazepine ring, was obtained along with spiro-N,N-ketal 2 via 2,2-condensation in the reaction of ninhydrin with naphthalene-1,8-diamine. Their molecular structures were elucidated by X-ray crystal structural analysis. Aside from these spiro compounds, the diazapleiadiene compound 3 formed by 1,2-condensation and the 1,4-isoquinolinedione compound 4 arising from ring expansion were isolated. When isatin was reacted with naphthalene-1,8-diamine, spiro-N,N-ketal 6 and the two 1H-perimidine-based compounds 7 and 8 were isolated. Compound 8 was revealed to undergo a fast dynamic prototropic tautomerization in solution. Plausible mechanisms of the formation of the products are proposed.

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Section: Resultssupporting

confidence: 82%

“…The reaction of isatin with naphthalene-1,8-diamine has also been described in the literature [20,21,22,23]. Here, we reinvestigated this reaction under the conditions involving the use of acetic acid as the solvent in the presence of a catalytic amount of p -toluenesulfonic acid.…”

Section: Resultsmentioning

confidence: 88%

Novel Rearrangements in the Reactions Directed Toward Preparation of Spiro-N,N-ketals: Reactions of Naphthalene-1,8-diamine with Ninhydrin and Isatin

et al. 2012

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“…2,3-Dihydro-1 H -perimidines were synthesized by the cyclo-condensation of NDA and different carbonyl compounds in the presence of InCl 3 in water at ambient temperature by Yasaei et al . [ 88 ]. Here, InCl 3 is a mild, inexpensive, easily available, non-toxic, and efficient catalyst, which produced perimidine derivatives in water as a “greener media” with high atom economy (Scheme 6 , Method 5).…”

Section: Perimidine Synthesis Under Different Conditionsmentioning

confidence: 99%

Recent Advances in the Synthesis of Perimidines and their Applications

Sahiba¹,

Agarwal²

2020

Top Curr Chem (Z)

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Perimidines are versatile scaffolds and a fascinating class of N-heterocycles that have evolved significantly in recent years due to their immense applications in life sciences, medical sciences, and industrial chemistry. Their ability of molecular interaction with different proteins, complex formation with metals, and distinct behavior in various ranges of light makes them more appealing and challenging for future scientists. Various novel technologies have been developed for the selective synthesis of perimidines and their conjugated derivatives. These methods extend to the preparation of different bioactive and industrially applicable molecules. This review aims to present the most recent advancements in perimidine synthesis under varied conditions like MW radiation, ultrasound, and grinding using different catalysts such as ionic liquids, acid, metal, and nanocatalyst and also under green environments like catalyst and solvent-free synthesis. The applications of perimidine derivatives in drug discovery, polymer chemistry, photo sensors, dye industries, and catalytic activity in organic synthesis are discussed in this survey. This article is expected to be a systematic, authoritative, and critical review on the chemistry of perimidines that compiles most of the state-of-art innovation in this area.

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“…To the best of our knowledge, there are very few reports available on the synthesis of dihydroperimidine derivatives using ketone. In earlier reports, protonic acids are used as catalyst to carry out above transformations with ketones (Borovlev et al, 2008;Bazgir et al, 2010). Higher acidity of these catalysts results into the formation of various byproducts, which in turn lower the yield of desired product.…”

Section: A R T I C L E I N F O Abstractmentioning

confidence: 99%