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CATEGORIES:College of Arts and Sciences,Thesis/Dissertations
DESCRIPTION:Title: Studies Toward Diverse Tricyclic Heterocycles Through Le
 wis Acid-Promoted Aza-Nazarov Cyclization by thamanna Begum Advisor:  Dr.
  Sivappa Rasapalli, Chemistry & Biochemistry Dept. Committee Members:  D
 r. Shuowei Cai, Chemistry & Biochemistry Dept. Dr. Wei-Shun Chang, Chemist
 ry & Biochemistry Dept. Abstract: Polycyclic alkaloids are valued structur
 es which are sought after in drug discovery for their bulky, rigid nature 
 and their wide range of pharmaceutical applications. Already found in natu
 re, these compounds exhibit antimicrobial, antifungal, and antitumor prope
 rties, which attract interest due to their potential in medicinal chemistr
 y. Being able to synthesize and redesign these molecules is an advantage t
 o optimize selectivity and precise binding to specific biological substrat
 es. However, conventional approaches to these architecturally complex fram
 eworks demand extensive experimental steps with low yields, limiting acces
 s to structural diversity. This research employs the Aza-Nazarov cyclizati
 on reaction to fold varying alkaloid precursors into tricyclic heterocycle
 s with great diversity in a single acid-catalyzed step. Precursors contain
 ing indole, benzimidazole, and imidazo[1,2- α]pyrimidine cores with diffe
 rent substituents were synthesized, featuring either typical Nazarov conju
 gated systems or α-ketoamides that serve as double-bond equivalents. Thes
 e were then subjected to a variety of Lewis acids in different conditions,
  including solvent systems, temperatures, and addition of catalysts, to pr
 omote ring closure with NMR and X-ray crystallography for structure determ
 ination. Optimizations of reaction conditions for improved purity and high
 er yield are ongoing. This thesis serves a purpose to extend the synthetic
  scope of Aza-Nazarov cyclization across multiple alkaloid frameworks, ena
 bling easier access to bioactive compounds with pharmacological prospectiv
 es.\nEvent page: https://www.umassd.edu/events/cms/8-5-26-thamanna-begum-s
 tudies-toward-diverse-tricyclic-heterocycles.php
X-ALT-DESC;FMTTYPE=text/html:<html><body><p>Title: Studies Toward Diverse T
 ricyclic Heterocycles Through Lewis Acid-Promoted Aza-Nazarov Cyclization 
 by thamanna Begum</p>\n<p>Advisor:<span style="mso-spacerun: yes\;">  </s
 pan>Dr. Sivappa Rasapalli\, Chemistry & Biochemistry Dept.</p>\n<p>Committ
 ee Members:<span style="font-family: 'Arial'\,sans-serif\;"> </span></p>
 \n<p>Dr. Shuowei Cai\, Chemistry & Biochemistry Dept.</p>\n<p>Dr. Wei-Shun
  Chang\, Chemistry & Biochemistry Dept.</p>\n<p>Abstract:</p>\n<p>Polycycl
 ic alkaloids are valued structures which are sought after in drug discover
 y for their bulky\, rigid nature and their wide range of pharmaceutical ap
 plications. Already found in nature\, these compounds exhibit antimicrobia
 l\, antifungal\, and antitumor properties\, which attract interest due to 
 their potential in medicinal chemistry. Being able to synthesize and redes
 ign these molecules is an advantage to optimize selectivity and precise bi
 nding to specific biological substrates. However\, conventional approaches
  to these architecturally complex frameworks demand extensive experimental
  steps with low yields\, limiting access to structural diversity. This res
 earch employs the Aza-Nazarov cyclization reaction to fold varying alkaloi
 d precursors into tricyclic heterocycles with great diversity in a single 
 acid-catalyzed step. Precursors containing indole\, benzimidazole\, and im
 idazo[1\,2- α]pyrimidine cores with different substituents were synthesiz
 ed\, featuring either typical Nazarov conjugated systems or α-ketoamides 
 that serve as double-bond equivalents. These were then subjected to a vari
 ety of Lewis acids in different conditions\, including solvent systems\, t
 emperatures\, and addition of catalysts\, to promote ring closure with NMR
  and X-ray crystallography for structure determination. Optimizations of r
 eaction conditions for improved purity and higher yield are ongoing. This 
 thesis serves a purpose to extend the synthetic scope of Aza-Nazarov cycli
 zation across multiple alkaloid frameworks\, enabling easier access to bio
 active compounds with pharmacological prospectives.</p><p>Event page: <a h
 ref="https://www.umassd.edu/events/cms/8-5-26-thamanna-begum-studies-towar
 d-diverse-tricyclic-heterocycles.php">https://www.umassd.edu/events/cms/8-
 5-26-thamanna-begum-studies-toward-diverse-tricyclic-heterocycles.php</a><
 /a></p></body></html>
DTSTAMP:20260716T170056
DTSTART;TZID=America/New_York:20260805T130000
DTEND;TZID=America/New_York:20260805T150000
LOCATION:VRB-210
SUMMARY;LANGUAGE=en-us:Studies Toward Diverse Tricyclic Heterocycles Throug
 h Lewis Acid-Promoted Aza-Nazarov Cyclization
UID:e439dd6ea398df13e0db08d1660fd226@www.umassd.edu
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