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SUMMARY:Synthesis of Novel Multi-functional Scaffolds from Sulfonyl Phthal
 ides
DTSTART:20230704T171500
DTEND:20230704T183000
DTSTAMP:20260407T111513Z
UID:727a8ab6655d493850f07e17dcae4f14f48d9878a679a8adf3269e2f
CATEGORIES:Conferences - Seminars
DESCRIPTION:Prof. Irishi N.N. Namboothiri\, Indian Institute of Technology
 \, Department of Chemistry\, Bombay\, India https://www.chem.iitb.ac.in/~i
 rishi/\nProfessor Irishi N N Namboothiri\n \nDepartment of Chemistry\, In
 dian Institute of Technology Bombay\, Mumbai 400 076\, irishi@iitb.ac.in\n
  \n[4+2] Annulation of stabilized phthalide anions as 1\,4-dipolar syntho
 ns with various Michael acceptors leading to benzannulated quinones\, espe
 cially naphthoquinones\, is popularly known as Hauser-Kraus (H-K) reaction
 . This reaction involving Michael addition followed by Dieckmann cyclizati
 on and elimination provided access to complex molecules\, including natura
 l products. Although several Michael acceptors have been successfully empl
 oyed in this reaction\, nitroalkenes have not received sufficient attentio
 n.   \n  \nIn the above scenario\, we reported the Hauser-Kraus annula
 tion of sulfonyl phthalides with nitroalkenes and other electron deficient
  alkenes. This involved a strategic variation of the reaction to [4+4] ann
 ulation by employing nitroalkenes bearing an additional nucleophilic site 
 resulting in complex fused and spiro-heterocycles. This strategy has been 
 extended to o-hydroxychalcones and o-hydroxyaryl para-quinone methides whi
 ch also afforded fused indenofurans and spiro-lactones.\n\nIn another appr
 oach\, synthesis of aminophenanthrenes\, including phenanthrene substitute
 d amino acids\, and benzoquinolines has been achieved using nitroalkenes b
 earing a key ketoalkyl moiety. A one-pot construction of functionalized sp
 iro-dihydronaphthoquinone-oxindoles via Hauser-Kraus annulation of sulfony
 l phthalide with 3-alkylideneoxindoles has also been reported by us.\n\nTh
 e unusual reactivity of sulfonyl phthalide with other substrates such as i
 satylidenemalononitrile\, activated imines\, O-protected salicylaldehydes 
 etc will also be discussed. \n \nReferences   \n\n[1] T. Kumar\, N. S.
  Satam and I. N. N. Namboothiri\, Eur. J. Org. Chem.  2016\, 3316.   \
 n[2] C. Sivasankara\, L. Satham and I. N. N. Namboothiri\, J. Org. Chem. 2
 017\, 82\, 12939.\n[3] T. Kumar\, V. Mane and I. N. N. Namboothiri\, Org. 
 Lett. 2017\, 19\, 4283.\n[4] A. Suresh\, T. V. Baiju\, T. Kumar and I. N. 
 N. Namboothiri\, J. Org. Chem. 2019\, 84\, 3158-3168.\n[5] P. Basu\, N.
  Satam and I. N. N. Namboothiri\, Org. Biomol. Chem. 2020\, 18\, 5677.\n
 [6] L. Satham\, A. Suresh and I N. N. Namboothiri\, Asian J. Org. Chem. 20
 21\, 10\, 1102.\n[7] N. Satam\, P. Basu\, S. Pati and I. N. N. Namboothiri
 \, Eur. J Org. Chem. 2021\, 3472.\n[8] P. Basu\, N. Satam\, S. Pati\, A. S
 uresh and I. N. N. Namboothiri\, J. Org. Chem. 2023\, 88\, 4038.\n[9] D. N
 air\, P. Basu\, S. Pati\, C. S. Sankara\, K. Baseshankar and I.  N. N. Na
 mboothiri\, J. Org. Chem. 2023\, 88\, 4519.\n[10] Account: C. S. Sankara\,
  S. P. Gaikwad and I. N. N. Namboothiri\, Synlett 2023\, 10.1055/a-2068-71
 26.
LOCATION:BCH 2201 https://plan.epfl.ch/?room==BCH%202201
STATUS:CONFIRMED
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