Microwave Induced Diastereoselective Synthesis of Spiro[indole‐oxiranes] and Their Conversion to Spiro[indole‐pyrazoles].

Abstract

Indole derivativesIndole derivatives R 0140 Microwave Induced Diastereoselective Synthesis of Spiro[indole-oxiranes] and Their Conversion to Spiro[indole-pyrazoles]. -Stereoselectivity of the title reaction depends on reaction time and power output, allowing for the selective synthesis of the (3RS, 3'SR) isomer (II) or the (3RS, 3'RS) isomer (IV). Results on antifungal and antitubercular activities are presented. -(DANDIA*, A.; SINGH, R.; SAHA, M.; SHIVPURI, A.; Pharmazie 57 (2002) 9, 602-605; Dep. Chem., Univ. Rajasthan,

Solvent‐free cycloaddition reaction of 3‐indolylimines with chloroacetyl chloride under microwave irradiation

“…The presence of fluorine in all synthesized compounds was confirmed by 19 F NMR spectra. Single fluorine attached to the indole ring and the CF 3 group attached to the phenyl ring appeared as singlets at δ −119.52 and −62.98 to −64.78 ppm, respectively.…”

“…Recently, we have also reported the effect of power level on diastereoselective synthesis of spiro oxirans [15]. Encouraged by this, we have studied the title cycloaddition reaction under different conditions of conventional and microwave-mediated synthesis using either triethylamine or K 2 CO 3 as basic catalyst respectively.…”

Synthesis of Aziridine‐ and Oxirane‐2‐phosphonates Spiro‐Fused with Oxindoles

“…[2] Spiro[oxindole-oxirane] ring systems are also of particular interest because of their biological applications as anticonvulsants, diuretics, sedatives, antifungal, and antitubercular agents. [3] In contrast, spiro[aziridine-oxindoles] have not been much studied. We have recently reported a novel synthesis of these compounds from oxindoles bearing a methylene or a vinylcarboxylate group in the α-position.…”

Facile One Pot Microwave Induced Solvent-Free Synthesis and Antifungal, Antitubercular Screening of Spiro [1,5]-Benzothiazepin-2,3'[3'H]indol-2[1'H]-ones

“…Many review articles [24][25][26][27][28][29][30] have been published in this field. Due to timeliness, ease of workability, dramatic rate enhancement and increased selectivity, microwave technology provides a promising alternative to environmentally unacceptable conventional procedures that may be time consuming or using toxic, expensive, problematic versus pollution and often flammable solvents in large amounts.Hence, we were encouraged by the vast potential of rapid and efficient solvent-less MW induced method that have manipulative advantages over heterogeneous reactions and in continuation to our earlier interest on the synthesis of various biodynamic spiro-3-indole derivatives [31][32][33][34][35][36][37][38] under MW irradiation. So, we report here in a facile and enviro-economic synthesis of the title compounds 7a-e incorporating two biologically important heterocycles (1,5-benzothiazepine and indole) with the assumption that the combination of these moieties may enhance the biological profile of the compound many fold versus its parent nuclei.…”

“…Hence, we were encouraged by the vast potential of rapid and efficient solvent-less MW induced method that have manipulative advantages over heterogeneous reactions and in continuation to our earlier interest on the synthesis of various biodynamic spiro-3-indole derivatives [31][32][33][34][35][36][37][38] under MW irradiation. So, we report here in a facile and enviro-economic synthesis of the title compounds 7a-e incorporating two biologically important heterocycles (1,5-benzothiazepine and indole) with the assumption that the combination of these moieties may enhance the biological profile of the compound many fold versus its parent nuclei.…”