A convenient synthesis of 3-cyano-4-imino-2-methylthio-4H-pyrimido [2,1-b] [1,3] benzothiazole and its reactions with selected nucleophiles

Pingle, Mayura S.; Vartale, Sambhaji P.; Bhosale, Vijay N.; Kuberkar, S. V.

doi:10.3998/ark.5550190.0007.a22

Cited by 20 publications

(5 citation statements)

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“…Treatment of the compound (3) with 5% aqueous sodium hydroxide under reflux afforded the traizole compound [4].…”

Section: Resultsmentioning

confidence: 99%

“…Forthemore, a band at 1670 was disappearance that attributed to υ C=O . The structure of the compound [4] has been also assigned by the U.V spectra Table (3). The mechanism is shown in Scheme (3) below [17].…”

Section: Resultsmentioning

confidence: 99%

“…Compound [3] (0.005mole) was reflux in NaOH (4%) for 5 hrs., cooled, poured into excess of water, stirred and filtered, on acidification of the filtered, the product was washed with cold water dried and recrystallized from ethanol. The physical properties of compound [4] is listed in Table (1) and the (C.H.N) analysis listed in Table (2). To compound (4) (0.01 mole) in absolute ethanol (20ml) was added potassium hydroxide (0.01 mole) and appropriate alkyl or aryl halide (0.012mole) ,the mixture was refluxed for (5hrs.…”

Section: *Synthesis Of [5-{4-[(7-nitro-213benzoxadiazol-4-yl) Amino]p...mentioning

confidence: 99%

“…IR spectra shows the disappearance of the band characterzing υ C=S , υ S-H in the expected region (1190, 2600) cm -1 . Figure [4] shows the FT-IR of compound (13).…”

Section: Scheme [5]mentioning

confidence: 99%

“…Many benzoxadiazole derivatives have been found to be considrable interest because of their biological activity [4,5,6] Some of these derivatives are useful anthiypers tensive agent [7], analgesic and for their antitbercular activity [8,9] further more ,several derivative have found to posses Herbicides [10], antifungal and anti cancer activity [11][12][13][14] .…”

Section: Introductionmentioning

confidence: 99%

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Preparation of Poly (N- Imidazolyl maleamic acid)

Ali¹,

Kadem²,

Rahi³

et al. 2012

JNUS

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Refluxing of the 4-chloro -7-nitro--2,1.3, -benzoxadiazole with ethyl (p-amino) benzoate in absolute ethanol at 78 C o for 12 hrs to give ethyl-4 -(7-nitro-2.1,3,-benzoxadiazole) -4-yl) amino benzoate (1) with 60% yield.Compound (1) was reacted with hydrazine hydrate in absolute ethanol for 5hrs to obtain the carboxylic acid hydrazide (2). The product (2) was treated with phenylisothiocyanat in absolute ethanol to synthesize 2-{4-[(7-nitro-2,1,3-benzoxadiazol-4-yl) amino] benzoyl}-Nphenylhydrazinecarbothioamide (3).Cyclization of the compound (3) using base has afforded 5-{4-[(7-nitro-2,1,3-benzoxadiazol-4-l) amino] phenyl} -4-phenyl-4H-1,2,4-triazole-3-thiol (4).The synthesized triazoles (4) derivative have been reacted once (alkyl ,aryl halides) and with appropriate secondary amine in dry dioxane to give (alkyl, aryl) thio derivative (5-9) and N-{4-[5-(N,N-substituted)-4-phenyl-4H-1,2,4-triazol-3-yl]phenyl}-7-nitro-2,1,3-benzoxadiazol-4-amine derivatives (11-13).The synthesized compounds have been characterized by their physical and chemical properties, spectral analysis (FT-IR, U.V) in addition to the micro analysis of the elements(C.H.N).

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“…Treatment of the compound (3) with 5% aqueous sodium hydroxide under reflux afforded the traizole compound [4].…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: *Synthesis Of [5-{4-[(7-nitro-213benzoxadiazol-4-yl) Amino]p...mentioning

confidence: 99%

“…IR spectra shows the disappearance of the band characterzing υ C=S , υ S-H in the expected region (1190, 2600) cm -1 . Figure [4] shows the FT-IR of compound (13).…”

Section: Scheme [5]mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Preparation of Poly (N- Imidazolyl maleamic acid)

Ali¹,

Kadem²,

Rahi³

et al. 2012

JNUS

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Regioselectivity in the Reaction of 2‐Aminobenzothiazoles and 2‐Aminobenzimidazoles with Enaminonitriles and Enaminones: Synthesis of Functionally Substituted Pyrimido[2,1‐b][1,3]benzothiazole and Pyrimido[1,2‐a]benzimidazole Derivatives

Alnajjar

Abdelkhalik

Riad

et al. 2018

Journal of Heterocyclic Chem

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A variety of new polyfunctionally substituted benzo[d]pyrimido[2,1‐b][1,3]thiazole and benzo[4,5]imidazo[1,2‐a]pyrimidine derivatives have been synthesized. The general synthetic procedure used for this purpose involves the condensation of 2‐aminobenzothiazole and 2‐aminobenzimidazole with a variety of enaminonitriles, enaminones, and acrylaldehyde. The regioselectivity for initial attack of either endocyclic ring nitrogen or exocyclic amino group was studied and rationalized for. It has been concluded that ring nitrogen is the most reactive cite in acidic medium, and cyclic intermediate can also be isolated, attesting to this conclusion upon cyclization. However, in basic or neutral medium, the exocyclic amino group was found to be the most reactive center. All structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, and alternative synthetic route whenever possible.

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Novel synthesis and biological activity of 2‐substituted derivatives of 3‐cyano‐4‐imino‐2‐methylthio‐8‐methoxy‐4H‐pyrimido[2,1‐b][1,3]benzothiazole and 3‐amino‐4‐imino‐8‐methoxy‐2H‐pyrazolo[3′,4′:4,5]pyrimido[2,1‐b][1,3]benzothiazole

Badne

Swamy

Bhosale

et al. 2011

Journal of Heterocyclic Chem

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2‐Amino‐6‐methoxybenzothiazole 1 on reaction with bis(methylthio)methylene malononitrile 2 in the presence of dimethyl formamide and catalytic amount of anhydrous potassium carbonate afforded 3‐cyano‐4‐imino‐8‐methoxy‐4H‐pyrimido[2,1‐b][1,3]benzothiazole 3. Under similar experimental conditions, compound 3 on treatment independently with arylamines/heterylamines/phenols/compounds containing active methylene group yielded corresponding 2‐substituted derivatives of compound 3 (4a, 4b, 4c, 4d, 5a, 5b, 5c, 6a, 6b, 6c, 6d, 6e, and 7a, 7b, 7c, 7d, 7e). Similarly, novel heterocyclic compounds, 3‐amino‐4‐imino‐8‐methoxy‐2H 8a/aryl 8b–c/heteryl 8d, 8e, 8f/pyrazolo[3′,4′:4,5]pyrimido[2,1‐b][1,3]benzothiazoles, were prepared by heating compound 3 independently with hydrazine hydrate/arylhydrazines/heterylhydrazines, respectively. All these newly synthesized compounds were screened for antimicrobial activity. J. Heterocyclic Chem., (2011).

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A convenient synthesis of 3-cyano-4-imino-2-methylthio-4H-pyrimido [2,1-b] [1,3] benzothiazole and its reactions with selected nucleophiles

Cited by 20 publications

References 9 publications

Preparation of Poly (N- Imidazolyl maleamic acid)

Preparation of Poly (N- Imidazolyl maleamic acid)

Regioselectivity in the Reaction of 2‐Aminobenzothiazoles and 2‐Aminobenzimidazoles with Enaminonitriles and Enaminones: Synthesis of Functionally Substituted Pyrimido[2,1‐b][1,3]benzothiazole and Pyrimido[1,2‐a]benzimidazole Derivatives

Novel synthesis and biological activity of 2‐substituted derivatives of 3‐cyano‐4‐imino‐2‐methylthio‐8‐methoxy‐4H‐pyrimido[2,1‐b][1,3]benzothiazole and 3‐amino‐4‐imino‐8‐methoxy‐2H‐pyrazolo[3′,4′:4,5]pyrimido[2,1‐b][1,3]benzothiazole

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