Synthesis of perimidine and 1,5-benzodiazepine derivatives using tamed Brønsted acid, BF3–H2O

Prakash, G. K. Surya; Paknia, Farzaneh; Narayan, Arjun; Mathew, Thomas; Oláh, George A.

doi:10.1016/j.jfluchem.2013.03.023

Cited by 23 publications

(6 citation statements)

References 53 publications

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“…Naphthalene is important aryl ring found in many biologically active compounds such as anti-inflammatory [1], anti-bacterial [2], anti-microbial [3] and anti-cancer agents [4]. 1,8-Diaminonaphthalene was used in synthesis of a limited number of naphtho[1,8- ef ][1,4]diazepine derivatives [5,6,7,8] and many perimidine derivatives [9,10,11,12]. Perimidines are an important class of heterocyclic systems due to their biological and pharmaceutical activities [9,10].…”

Section: Introductionmentioning

confidence: 99%

“…1,8-Diaminonaphthalene was used in synthesis of a limited number of naphtho[1,8- ef ][1,4]diazepine derivatives [5,6,7,8] and many perimidine derivatives [9,10,11,12]. Perimidines are an important class of heterocyclic systems due to their biological and pharmaceutical activities [9,10]. They have been used as anti-ulcer, anti-microbial, and anti-fungal agents [11,12].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

et al. 2014

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Two series of naphtho[1,8-ef][1,4]diazepines and pyrrolo[1,2-a]perimidines were prepared starting from 1,8-diaminonaphthalene and hydrazonoyl chlorides. The structures of the products were determined on the basis of their spectral data and elemental analyses. The mechanism of formation of such products was also discussed. The prepared compounds were screened for their antitumor activity against three cell lines, namely, MCF-7, TK-10 and UACC-62, and some derivatives showed promising activity.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

et al. 2014

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“…In the second method, NDA was refluxed with 2-alkoxycarbonylmethylene substituted furan-3-ones in methanol and corresponding perimidines were produced in good yields (72–79%) (Scheme 5 , Method 3). Prakash and companions [ 73 ] disclosed a simple, one-pot and high-yielding protocol for the synthesis of perimidine derivatives using BF 3 ·H 2 O Brønsted acid as an effective catalyst and solvent from the cyclocondensation of NDA and various ketones in ethanol at ambient temperature via eco-benign pathways (Scheme 5 , Method 4).…”

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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“…HBOB, PTSA, BF 3 -H 2 O, chitosan hydrochloride, squaric acid, sulfamic acid, etc. were used for the synthesis of this moiety [18][19][20][21][22][23][24][25][26][27][28] .…”

Section: Introductionmentioning

confidence: 99%

Metal Free Sulfonic Acid Functionalized Carbon Catalyst for Green and Mechanochemical Synthesis of Perimidines

Sahiba¹,

Sethiya²,

Soni³

et al. 2020

ChemistrySelect

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A new and scalable mechanochemical approach has been developed for the synthesis of perimidine derivatives using an efficient and recyclable catalyst, carbon sulfonic acid under metal-free conditions. A wide variety of aldehydes displayed cyclo-condensation reaction with 1,8-diaminonaphthalene in EtOH under ambient reaction conditions via grind-stone technique to produce substituted perimidines in excellent yields (95-99 %) in a very short reaction time. This method has interesting features like single-step synthesis, high functional group tolerance, transition-metal free synthesis, high atomeconomy, recyclable catalyst, no need of tedious purification process, gram-scale synthesis, high green chemistry matrix (Eco-score and E-factor) that make this protocol green and ecofriendly.

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Synthesis of perimidine and 1,5-benzodiazepine derivatives using tamed Brønsted acid, BF3–H2O

Cited by 23 publications

References 53 publications

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

Synthesis of 2-Phenylazonaphtho[1,8-ef][1,4]diazepines and 9-(3-Arylhydrazono)pyrrolo[1,2-a]perimidines as Antitumor Agents

Recent Advances in the Synthesis of Perimidines and their Applications

Metal Free Sulfonic Acid Functionalized Carbon Catalyst for Green and Mechanochemical Synthesis of Perimidines

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