Methyl 2-oxo-2,3-dihydro-1,3-benzothiazole-3-acetate

Akkurt, Mehmet; Yıldırım, Sema Öztürk; Baryala, Yamna; Zerzouf, Abdelfettah; Essassi, E. M.; Büyükgüngör, Orhan

doi:10.1107/s1600536805034264

Cited by 2 publications

(2 citation statements)

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“…All geometric parameters are in agreement with the corresponding ones for similar compounds. 5,6 The benzothiazole groups are essentially planar, with maximum deviations of 0.014(1), -0.012(2) and -0.013(1)Å for atoms C1, C4 and C7, respectively. The imidazol groups are slightly off the benzothiazole plane.…”

Section: Structure Of N-(13-benzothiazol-2-yl)-n-[1-(piperidin-4-ylmethyl)-45dihydro-1h-imidazol-2-yl]amine Cmentioning

confidence: 99%

Structure of N-(1,3-Benzothiazol-2-yl)-N-[1-(piperidin-4-ylmethyl)-4,5-dihydro-1H-imidazol-2-yl]amine, C16H21N5S

et al. 2006

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2-Arylamino-2-imidazolines have an interesting chemistry, 1,2 and are effective pharmacophores in medicinal chemistry. 2-Arylamino-2-imidazolines, particularly 2,6dichlorophenylamino-2-imidazoline (clonidine), have a pronounced, hypotensive action, which is coupled with a sedative action. Moreover, some of these compounds also have a more or less pronounced analgesic action, which, however, because of the simultaneous existence of the hypotensive action and the depressant action on the central nervous system, was considered to be unexploitable. 3 In this study, as the starting material, dimethyl N-aryldithioimidocarbonate (1) was synthesized from carbon disulfide, aromatic amine, and methyl iodide in the presence of concentrated aqueous NaOH. The synthesis of N-(1,3-benzothiazol-2-yl)-N-(4,5-dihydro-1Himidazol-2-yl)amine (2) was carried out by both conventional heating and by microwave irradiation according to cited references. 4 Its piperidine-4-yl methyl derivative (3) was synthesized by treatments with piperidine and formaldehyde.A solution of N-(1,3-benzothiazol-2-yl)-N-(4,5-dihydro-1Himidazol-2-yl)amine (2) (0.01 mol) in methanol (20 mL) was stirred at room temperature for 2 h with aqueous formaldehyde (35%; 0.015 mol) and 0.01 mol piperidine (1 mL, d: 0.86 g cm -3 ). The solvent was removed on a rotary evaporator. The residue was mixed with methanol, and the precipitate formed was filtered and then recrystallized from chloroform (yield 67%, mp 432 K).

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Section: Structure Of N-(13-benzothiazol-2-yl)-n-[1-(piperidin-4-ylmethyl)-45dihydro-1h-imidazol-2-yl]amine Cmentioning

confidence: 99%

Structure of N-(1,3-Benzothiazol-2-yl)-N-[1-(piperidin-4-ylmethyl)-4,5-dihydro-1H-imidazol-2-yl]amine, C16H21N5S

et al. 2006

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“…1,4-Benzothiazine and its derivatives have attracted intense interest in recent years because of their diverse pharmacological properties (Akkurt, Ö ztü rk Yıldırım et al, 2005;Akkurt, Tü rktekin et al, 2005;Wang et al, 2005;Aravindan et al, 2003); some of these compounds exhibit antimicrobial (Habib et al, 1997;Sastry et al, 1990;Rao et al, 1982Rao et al, , 1983, antibacterial (Desai & Mehta, 1997;Miky et al, 1997), antifungal (Chaffman & Brogden, 1985), anti-oxidant (Vladimirov et al, 1991), antiviral (Ergen et al, 1996), anti-HIV-1 (Invidiata et al, 1996) and antihypertensive activities (Kando & Hashimoto, 1993;Keita et al, 2000).…”

mentioning

confidence: 99%