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Review on Perimidines: A synthetic Pathways Approach

Ganesh B. Yelmame1*and Shrikant B. Jagtap2

1Department of Chemistry, Mahatma Gandhi Vidyamandir’s SPH.Arts, Science and Commerce College, (Affiliated to SP Pune University, Pune) Nampur, Nashik-423 204, India 

2Departmen in Chemistry, Pune District Education Association’s Annasaheb Magar Mahavidyalaya, (Affiliated to Savitribai Phule Pune University, Pune) Hadapsar, Pune- 411028, India 

Corresponding Author E-mail: yelmameganesh@gmail.com

DOI : http://dx.doi.org/10.13005/msri/180103

Article Publishing History
Article Received on : 20-Mar-2020
Article Accepted on : 14-Apr-2021
Article Published : 16 Apr 2021
Plagiarism Check: Yes
Reviewed by: Dr. Guru Swamy
Second Review by: Dr. Yogesh Chaudhari
Final Approval by: Dr. Ajay Mishra 
Article Metrics
ABSTRACT:

Perimidines are available in an assortment of drugs and general use industrial structures and perimidines are also significant primary theme because of their extraordinary method of physiological activity. Thus the underlying significance of perimidine moiety has evoked a lot of interest in the field of natural blend and compound science to build up some better than ever amalgamation of this atomic skeleton. In this review, we have depicted a modern outline on the new advances in the different manufactured approaches of perimidine. The review covers the essential applied and down to earth synergist blend like, green methodologies, metal catalysed responses, microwave illumination, grinding and so forth which are critical for developing perimidine skeleton. This review will fulfil the assumptions for peruses who are keen on the advancement of the field and searching for an update. It will animate analysts to grow new and innovative manufactured admittance to this heterocyclic framework, which will be instrumental in the headway of perimidine science.This review provides an overview of various synthetic methodologies for the synthesis of a wide range of perimidine derivatives with applications in material chemistry, drug discovery, polymer chemistry, photo sensors, dye chemistry, and other fields.

KEYWORDS: 8 Diamino Naphthalene; Green Chemistry; Grinding; Perimidine

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Yelmame G. B, Jagtap S. B. Review on Perimidines: A synthetic Pathways Approach. Mat. Sci. Res. India;18(1).

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Yelmame G. B, Jagtap S. B. Review on Perimidines: A synthetic Pathways Approach. Mat. Sci. Res. India;18(1). Available from: https://bit.ly/2PZKEQl

Introduction

Perimidine is synthesized by inserting a one-carbon unit between the nitrogen and closing the ring of 1,8-naphthalenediamine. Heteroaromatic structure displaying the distinct properties of compounds with abundance and deficit of electrons at the same time. Perimidine is one such framework, and its amphoteric chemical properties make it a fascinating research topic. Perimidine derivatives are explored in terms of polymer chemistry, drug discovery, photo sensors, dye industries, and catalytic action in organic synthesis 1. Perimidines and the pyrimidine fused with naptha framework is a relatively recent and rapidly expanding field of pure and applied chemistry. Structure, synthesis, spectral experiments, bonding with numerous motifs and ligands, andtheir varied reactivity in a variety of fields.Researchers are particularly interested in its environmentally friendly synthesis because of its unusual electronic properties and wide range of applications. Green Chemistry has emerged as new branch of chemistry for the synthesis of variety of compounds by employing green chemistry principles2-15. Various correspondences have been focussed in recent years to the biological activity of perimidines. Heterocyclic compounds were investigated to show wide of variety of biological properties 16-28. As a result of this concern, numerous perimidine and composite synthesis methodologies have been established. A significant number of perimidines have been designed under various conditions to date. Writing reports uncover that perimidines are of wide intrigue in view of their expansive range of biological activities[29-30]. Perimidines exhibit antihelminthic activity 31-33. Neurotropic active systems (stimulants and depressants of the central nervous system have been found out by using perimidines 34–36. Some compounds reveals good antitumor 37–40, antagonist41, antibacterial and antifungal42 activities. 2-(R’-oxymethyl)-perimidine derivatives have been proposed as highly effective antiulcer agent43. Some perimidine derivatives acts as antineoplastic agents44. Heterocyclic perimidines show antimicrobial45  and anorectic46 activity.The aim of the study is to highlight the most recent developments in perimidine synthesis under a variety of conditions.

Synthetic Pathways to Perimidines

An acid-catalyzed reaction of carboxylic acids and 1,8-diaminonapthalene(Scheme 1) gives 2-substituted perimidine under microwave irradiation47.

Scheme 1

Vol18No1_Rev_Gan_sch1
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1,8-diaminonaphthalene reacts with 1,3,5-triazine in presence of polyphosphoric acid(Scheme 2) leads to perimidine 48.

Scheme 2

Vol18No1_Rev_Gan_sch2
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Various perimidine derivatives aresynthesized from naphthalene-1,8-diamine and variety of ketone functionality(Scheme 3) using catalyst BiCl3 49.

Scheme 3

Vol18No1_Rev_Gan_sch3
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Perimidine can be synthesized using ruthenium (III) chloride (Scheme 4) under mild condition 50

Scheme 4

Vol18No1_Rev_Gan_sch4
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Different organically significant perimidine subordinates have been effectively orchestrated in amazing yields utilizing naphthalene-1,8-diamine with different ketones (Scheme 5) within the sight of a synergist measure of Yb(OTf)3 51

Scheme 5

Vol18No1_Rev_Gan_sch5
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Another course to perimidines has been created which includes response of a 1,8-diaminonaphthalenewith chloro oxime derivative (Scheme 6) 52

Scheme 6

Vol18No1_Rev_Gan_sch6
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In the presence of a catalytic volume of Cu(NO3)2.6H2O in ethanol at room temperature, some perimidine subordinates is mixed by condensation reaction of 1,8 diaminonaphthalene and aromatic aldehydes. (Scheme 7) 53

Scheme 7

Vol18No1_Rev_Gan_sch7
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Perimidine is formed by reacting 1,8-diaminonaphthalene with aromatic aldehydes in the presence of NaY zeolite at room temperature. (Scheme 8) 54.

Scheme 8

Vol18No1_Rev_Gan_sch8
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The cyclocondensationmethod of various aromatic aldehydes with 1,8diaminonaphthalene in the presence of nano-silica sulfuric acid (NSSA) as a catalyst has been used to create a reliable and direct method for the synthesis of perimidine subordinates. (Scheme 9) 55.

Scheme 9

Vol18No1_Rev_Gan_sch9
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Perimidines are produced by reacting 1,8-diaminonaphthalene with aromatic aldehydes at room temperature in the presence of NaY zeolite. (Scheme 10) 56.

Scheme 10

Vol18No1_Rev_Gan_sch10
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The reaction of naphthalene-1,8-diamine and active carbonyl compounds in water at room temperature showed InCl3 to be a mild and viable impetus for the simple and fruitful union of spiro-perimidine subsidiaries. (Scheme 11) 57.

Scheme 11

Vol18No1_Rev_Gan_sch11
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The study explores the catalytic activity of H3PW12O40/NaY and H3PW12O40/NaY/MCM-41 hybrid materials in the synthesis of perimidine (Scheme 12) 58.

Scheme 12

Vol18No1_Rev_Gan_sch12
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By building up aryl diamines with -carbonyl mixtures catalysed by ytterbium chloride, an effective technique for combining functionalized benzimidazoles and perimidines is developed (Scheme 13) 59.

Scheme 13

Vol18No1_Rev_Gan_sch13
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The multicomponent reaction of heterocyclic ketene aminals with dialkylacetylenedicarboxylates in the presence of DMAP is a suitable technique for the preparation of isoindole derivatives (Scheme 14)60.

Scheme 14

Vol18No1_Rev_Gan_sch14
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Using boric acid (HBOB) as a catalyst and ketone as a substrate, an efficient method for the synthesis of substituted perimidine derivatives is described (Scheme 15) 61.

Scheme 15

Vol18No1_Rev_Gan_sch15
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Another and proficient admittance to (Z)-N-(2-argio-1-(1H-perimidin-2-yl)vinyl)benzamide subsidiaries from promptly accessible substrates in HOAc is depicted with help of microwave irradiation (Scheme 16)62.

Scheme 16

Vol18No1_Rev_Gan_sch16
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The reaction of 1,8-diaminonaphthalene and aromatic aldehydes in the presence of molecular iodine as a highly active catalyst yielded a few perimidines in high to exceptional yields (Scheme 17) 63.

Scheme 17

Vol18No1_Rev_Gan_sch17
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Using cyclocondensation of various aldehydes and ketones with 1,8-diaminonaphthalene in ethanol as a solvent at room temperature, sulfonated ordered nanoporous carbon effectively catalyses the synthesis of perimidines (Scheme 18) 64.

Scheme 18

Vol18No1_Rev_Gan_sch18
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The reaction of 1,8-diaminonapthalene with iminoester hydrochlorides of substituted phenylacetic acids with microwave irradiation is identified for the synthesis of 2-substituted perimidines (Scheme 19) 65.

Scheme 19

Vol18No1_Rev_Gan_sch19
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Synthesis of Perimidine and 1,5-Benzodiazepine Derivatives Using Tamed Brønsted Acid, BF3-H2O as a catalyst (Scheme 20) 66.

Scheme 20

Vol18No1_Rev_Gan_sch20
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Another technique for union of 2-aryl-2,3-dihydro-1Hperimidines by buildup of 1,8-diaminonaphthalene with a variety of aromatic aldehydes utilizing nano-CuY zeolite as catalyst, in ethanol, at room temperature (Scheme 21) 67.

Scheme 21

Vol18No1_Rev_Gan_sch21
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A proficient convention has been created to incorporate different dihydro-1H-perimidine subordinates utilizing financially accessible Amberlyst-15 as a catalyst (Scheme 22) 68.

Scheme 22

Vol18No1_Rev_Gan_sch22
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A successful union of different organically significant 2,3-dihydroperimidines from response of aldehydes and naphthalene-1,8-diamine has been created utilizing [BTBA] Cl-FeCl3 as an effective Lewis corrosive ionic fluid (Scheme 23) 69.

Scheme 23

Vol18No1_Rev_Gan_sch23
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Functionalized magnetic center shell nanoparticles  arranged by co-precipitation strategy, is a powerful and recyclable catalyst for the combination of imidazole, benzothiazole, and perimidine subsidiaries, under solvent free conditions (Scheme 24) 70.

Scheme 24

Vol18No1_Rev_Gan_sch24
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Nanoparticles as an efficient catalyst for synthesis of mono-, bis-, tris- and spiro-perimidines have been reported (Scheme 25) 71.

Scheme 25

Vol18No1_Rev_Gan_sch25
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Gentle and relevant blend of mono-, bis-, and spiro-perimidines is exhibited in significant yields by means of the buildup of 1,8- diaminonaphthalene and aldehydes or ketones in presence of sulfamic acid as a green and exceptionally effective catalyst (Scheme 26) 72.

Scheme 26

Vol18No1_Rev_Gan_sch26
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An easy immediate technique to blend the perimidine under dissolvable free conditions as another strategy is accounted under microwave irradiation (Scheme 27) 73.

Scheme 27

Vol18No1_Rev_Gan_sch27
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The response of 1,8-diaminonaphthalene with aromatic aldehydes gave 2-subbed perimidines within the sight of FePO4 as a flexible, green and reusable impetus at room temperature (Scheme 28)74.

Scheme 28

Vol18No1_Rev_Gan_sch28
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Synthesis of 2,3-dihydo-1H-perimidines subordinates was set up by considering a response between naphthalene-1,8-diamine and ketone within the sight of Phenyl boronic corrosive as an catalyst utilizing ethanol as a solvent (Scheme 29) 75.

Scheme 29

Vol18No1_Rev_Gan_sch29
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Exceptionally powerful heterogeneous impetus for improving the cyclocondensation response of 1,8-diaminonaphthalene with fragrant aldehydes to get 2,3-dihydro-1H-perimidine subsidiaries (Scheme30) 76.

Scheme30

Vol18No1_Rev_Gan_sch30
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A novel attractive nanocatalyst as a green, efficient and recoverable nanocatalyst pyrimidine subsidiaries could be effortlessly arranged utilizing this novel nanocatalyst in brilliant yields (Scheme 31) 77.

Scheme 31

Vol18No1_Rev_Gan_sch31
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Nano-g-Al2O3/SbCl5 has been utilized for combination of 2-subbed perimidines by means of response of naphthalene-1,8-diamine with different aldehydes at room temperature under dissolvable free conditions (Scheme 32) 78.

Scheme 32

Vol18No1_Rev_Gan_sch32
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The reactant movement of SiO2 nanoparticles (NPs) as an eco-friendly, efficient and reusable impetus in the combination of 2,3-dihydro-1H-perimidines was found out (Scheme 33) 79.

Scheme 33

Vol18No1_Rev_Gan_sch33
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Proficient amalgamation of perimidine subordinates utilizing recently used chitosan hydrochloride was created (Scheme 34) 80.

Scheme 34

Vol18No1_Rev_Gan_sch34
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Fe3O4-stacked sulfonated zeolite was applied as a novel multi-functional zeolite impetus for the blend of perimidine subsidiaries (Scheme 35) 81.

Scheme 35

Vol18No1_Rev_Gan_sch35
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Fe3O4@NCs/BF0.2 was utilized for the amalgamation of 2,3-dihydro-1H-perimidine subsidiaries through a response of 1,8-diaminonaphthalene with different aldehydes at room temperature under dissolvable free conditions (Scheme 36) 82.

Scheme 36

Vol18No1_Rev_Gan_sch36
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The Mn-catalyzed dehydrogenative amalgamation of primarily significant 2,3-dihydro-1H-perimidines has been illustrated (Scheme 37) 83.

Scheme 37

Vol18No1_Rev_Gan_sch37
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The synergist execution of Ni/TCH@SBA‐15 (NNTS‐15) was resolved for the amalgamation of 2,3‐dihydroperimidines (Scheme 38)84.

Scheme 38

Vol18No1_Rev_Gan_sch38
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Hybrid nanomaterial was utilized as an effective impetus in the one-pot,green and straightforward convention for the combination of spiroperimidine subsidiaries (Scheme 39) 85.

Scheme 39

Vol18No1_Rev_Gan_sch39
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Squaric acid, a green, without metal and eco-accommodating organocatalyst, has been abused for the union of organically fascinating 2,3-dihydro-1H-perimidines (Scheme 40) 86.

Scheme 40

Vol18No1_Rev_Gan_sch40
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An epic amalgamation of profoundly combined perimidine subsidiaries was accomplished in two stages from 2-alkynylbenzaldehydes. Copper-catalyzed annulation of 2-[(2bromophenyl)ethynyl]benzaldehydes with 1,8-diaminonaphthalene created dihydroisoquinolino[2,1-a]perimidines (Scheme 41) 87.

Scheme 41

Vol18No1_Rev_Gan_sch41
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A Cu(OAc)2-catalyzed chain reaction tricyclization of naphthalene-1,8-diamine and 2-(phenylethynyl) benzaldehyde is described, allowing oxygen-consuming oxidative dehydrogenation coupling to heptacyclic quinolizin o[ 3,4,5,6-kla]perimidines to be obtained Scheme 42)88.

Scheme 42

Vol18No1_Rev_Gan_sch42
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Spiro[1,3-dihydroperimidine-2,9-fluorene] and its co-crsytal with 9-fluoreone have been synthesized with the help of acetic acid as a catalyst (Scheme 43) 89.

Scheme 43

Vol18No1_Rev_Gan_sch43
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A few extremely successful one-pot manufactured methodswere established, allowing polyphosphoric acid activated nitroalkanes to act as electrophiles in aminonapthalene reactions. The methods illustrated consider the single-step set of polyheterocyclic aromatic subsidiaries of the 6H-pyrrolo[2,3,4-gh] perimidine platform in substantial returns. (Scheme 44)  90.

Scheme 44

Vol18No1_Rev_Gan_sch44
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A active one-pot mix of two new heterocyclic perimidines, 4-(2,3-dihydro-1H-perimidin-2-yl)-2-methoxyphenol and 2-(2,3-dihydro-1H-perimidin-2-yl)-2-methoxyphenol and 2-(2,3-dihydro-1H-perimidin-2-yl)-2-meth (quinoxalin-2-yl) – Strong yields of 2,3-dihydro-1H-perimidine are produced. (Scheme 45)91.

Scheme 45

Vol18No1_Rev_Gan_sch45

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For the union of perimidines, another green protocol was established. The protocol involves a dissolvable and impetus-free reaction of ethoxycarbonylhydrazone with 1,8diaminonaphthalene. (Scheme 46) 92.

Scheme 46

Vol18No1_Rev_Gan_sch46

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The most environmentally sustainable method for mixing 2,3-dihydro-1H-perimidines with water is demonstrated. At room temperature, 1,8-diamino naphthalene was reacted with a variety of aldehydes to equip the item in low to high yields. (Scheme 47) 93.

Scheme 47

Vol18No1_Rev_Gan_sch47

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For the synthesis of 2,3-dihydro-1H-perimidines,  benign, efficient, and green granulating assisted technique has been developed. The 1,8-diaminonaphthalene and aldehydes were ground for 5 minutes in a mortar and pestle, resulting in moderate to excellent yields (Scheme 48) 94.

Scheme 48

Vol18No1_Rev_Gan_sch48

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Conclusions

Perimidine synthesis remains a highly active area of research due to its diverse range of natural exercises, and its readiness will continue to be a significant task in the future. The development of manufactured routes for the preparation of perimidines has progressed in ways previously deemed challenging. In this report, an attempt was made to cover all of the major events and developments in science over the last few decades, which have seen exponential growth. These new reactions produce highly functionalized perimidines in good to excellent yields. A few approaches cover more recent techniques, cleaner synthetic substances that are not toxic to the environment, both of which lead to enhancing blend courses, reducing reaction projects, and making the relationship greener. Regardless of these developments, further work on designing new perimidine methods is expected. To offer pathways to the formation of neglected perimidines, new impetuses and synthetic improvements are needed, resulting in the disclosure of perimidines with new properties and natural exercises. We conclude this survey by hoping that it will inspire scientists to develop new and inventive manufactured access routes to this heterocyclic system, which will be critical in the advancement of many fields of research.

Acknowledgment

The authors acknowledge the Department of Chemistry, Mahatma Gandhi Vidyamandir’s SPH.Arts, Science and Commerce College, Nampur and Department of Chemistry, Pune District Education Association’s AnnasahebMagarMahavidyalaya, Hadapsar, Pune for providing necessary facilities.

Conflict of Interest 

No potential conflict of interest was reported by the authors.

Funding Source

We have not received any kind of fund for the research work.

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