Chemoselectivity of indole-dicarboxylates towards hydrazine hydrate: Part III - Synthesis and antimicrobial activity of novel 4-thiazolidinonylindoles

156-159Exclusive formation of 3-carbethoxyindol-5-yloxyacetic acid hydrazides <b style="mso-bidi-font-weight: normal">3a,b from 3-carbethoxy-5- ethoxycarbonylmethoxyindoles 2a,b reveals the chemoselectivity of the C5-methyl ester function towards the nucleophilic attack of hydrazine hydrate. These mono hydrazides 3a,b on reacting with benzaldehydes furnish 1-alkyl-5- benzalhydrazinocarbonylmethoxy-3-ethoxycarbonyl-2-methylindoles 5a-h which on treatment with thioglycolic acid afford the desired 1-alkyl-3-ethoxycarbonyl-2-methyl-5-[(2-phenyl-4-thiazolidinon-3-yl)aminocarbonylmethoxy] indoles 6a-h. All the new compounds have been screened for their antibacterial and antifungal activities. </span

<span style="font-size:12.0pt;font-family: "Times New Roman";mso-fareast-font-family:"Times New Roman";mso-ansi-language: EN-IN;mso-fareast-language:EN-IN;mso-bidi-language:AR-SA" lang="EN-IN">One pot synthesis of novel 5, 11-dioxo-6-methyl-5,9,10,11-tetrahydro-8<i style="mso-bidi-font-style: normal">H</i>-naphth[2,3:1,2]pyrrolizine and its 9-acetoxy analogue</span>

1123-11255, 11-dioxo-6-methyl-5,9,10,11-tetrahydro-8<i style="mso-bidi-font-style: normal">H-naphth[2,3:1,2]-pyrrolizine <span style="font-size:12.0pt; font-family:" times="" new="" roman";mso-fareast-font-family:"times="" roman";="" mso-ansi-language:en-in;mso-fareast-language:en-in;mso-bidi-language:ar-sa"="" lang="EN-IN">5a and its 9-acetoxy analogue <b style="mso-bidi-font-weight: normal">5b are prepared in a one-flask procedure by the reaction of L-proline 1a or 4-hydroxy-L-proline 1b with refluxing acetic anhydride and olefinic dipolarophile 1,4-naphthoquinone 4.</span