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Title: Synthesis of some potential biologically active quinazolyl, quinolyl, isoquinolinyl and indazolyl derivatives containing alfa-hydroxy carboxylic acid moieties as substituents
Researcher: Suresh, T
Guide(s): Acharyulu, Palle V R
Keywords: Chemistry
Upload Date: 19-Apr-2012
University: Jawaharlal Nehru Technological University
Completed Date: August, 2010
Abstract: Chapter 1: General introduction: This chapter deals with the introductory aspects of -hydroxy carboxylic acids, quinazolinones, quinolines, isoquinolinones and indazoles, their importance, synthesis and chemical properties. Chapter-2: Section A: STUDIES ON SYNTHESIS OF -HYDROXY CARBOXYLIC ACIDS To a solution of optically pure L-amino acids (34a-f) in 6% H2SO4 and acetone (1:1 ratio), were added 3 molar equivalents of sodium nitrite in water solution at 0°C to furnish -hydroxy carboxylic acids (35a-f) in good yields. (Scheme 2.1) Scheme 2.1: R NH2 O OH R OHO OH 34a-f 35a-f Reaction conditions: H2SO4/NaNO2/ H2O/Acetone/ (-) 50C-RT Chapter-2: Section-B Synthesis of 3-aryl-2 quinazolinyl-phenylacetic acid ester derivatives The Section describes the design and synthesis of novel quinazolinone derivatives like 2-(2-(4-((3,4-dihydro 4-oxo-3- arylquinazolin-2-yl)methyl) piperazin-1-yl)acetoyloxy)-2-phenyl acetic acid esters (57) incorporating three biologically active moieties such as quinazolinone, piperazine and (2S)-2-hydroxy-2-phenylacetic acid derivatives in a single molecule. Reaction of 58 with 59 in presence of K2CO3 and KI, gave the title compound, 2-(2 (4-((3,4-dihydro-4-oxo-3-arylquinazolin-2-yl)methyl) piperaz -in-1-yl)acetoyloxy)-2 phenyl acetic acid esters (57). The structures of all the new compounds obtained in the present work are supported by spectral and analytical data. (Scheme 2.24) Scheme-2.24 O O OR ON N N NO Ar O O OR OCl N HN N NO Ar + 58 59 57 i Reagents and Conditions: i) K2CO3, KI, CH3CN, Δ. The reaction of 2-(chloromethyl)-3-(2-methylphenyl)-3,4-dihydro-4- quinazolinone 62c (22) (i.e.66c, Ar= C6H4-OCH3-3) with 4- Piperidone/morpholine/4-ethyl piperidinecarboxylate, K2CO3 and KI, under refluxing acetonitrile for 90-120 min. resulted in the formation of 64/65/66. (Scheme 2.25)
Pagination: 235p.
Appears in Departments:Faculty of Chemistry

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01_title.pdfAttached File167.2 kBAdobe PDFView/Open
02_declaration.pdf186.02 kBAdobe PDFView/Open
03_certificates.pdf295.1 kBAdobe PDFView/Open
04_acknowledgements.pdf109.18 kBAdobe PDFView/Open
05_abstract.pdf270.71 kBAdobe PDFView/Open
06_methodology & instrumentation.pdf85.91 kBAdobe PDFView/Open
07_abbreviations.pdf140.98 kBAdobe PDFView/Open
08_contents.pdf338.84 kBAdobe PDFView/Open
09_chapter 1.pdf367.91 kBAdobe PDFView/Open
10_chapter 2.pdf405.44 kBAdobe PDFView/Open
11_chapter 3.pdf390.09 kBAdobe PDFView/Open
12_chapter 4.pdf421.9 kBAdobe PDFView/Open
13_chapter 5.pdf752.86 kBAdobe PDFView/Open

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