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Page 75
conferenceseries.com
July 17-19, 2017 Chicago, USA
3rd International Conference on
Organic and Inorganic Chemistry
Volume 6, Issue 2 (Suppl) Organic Chem Curr Res, an open access journal
ISSN:2161-0401 Organic Chemistry 2017
July 17-19, 2017
Organic Chem Curr Res 2017, 6:2 (Suppl)
DOI: 10.4172/2161-0401-C1-020
Adventure with alkynes: Modern tool for the synthesis of heterocycles, natural products-like and
π-conjugated scaffolds from alkynes
Akhilesh Kumar Verma
University of Delhi, India
S ynthesis of small heterocyclic molecules in terms of selectivity, operational simplicity, functional group tolerance and
environmental sustainability are in constant demand as majority of drugs; drug-like compounds contain hetero atom at
their core. In continuation of our interest in the synthesis of heterocycles using alkynes, we have successfully engineered the
synthesis of variety of biologically important heterocyclic scaffolds using electrophilic cyclization/hydroamination/and alkyne
annulations. In this presentation the author would like to discuss about recent results in this chemistry.
Synthesis of functionalized-2-aryl-2, 3-dihydroquinoline-4(1H)-ones via Fries rearrangement of C-3
conjugated azetidin-2-ones
Parvesh Singh1, Vishu Mehra2 and Vipan Kumar2
1University of Kwa-Zulu Natal, South Africa
2Guru Nanak Dev University, India
Quinoline-4-ones represent an important class of heterocyclic scaffolds that have attracted significant interest due to their
various biological and pharmacological activities. This heterocyclic unit also constitutes an integral component in drugs
used for the treatment of neurodegenerative diseases, sleep disorders and in antibiotics viz. norfloxacin and ciprofloxacin.
The synthetic accessibility and possibility of fictionalization at varied positions in quinoline-4-ones exemplifies an elegant
platform for the designing of combinatorial libraries of functionally enriched scaffolds with a range of pharmacological
profles. They are also considered to be attractive precursors for the synthesis of medicinally imperative molecules such as
non-steroidal androgen receptor antagonists, antimalarial drug chloroquine and martinellines with antibacterial activity.
2-Aryl-2, 3-dihydroquinolin-4(1H)-ones are present in many natural and non-natural compounds and are considered to be
the aza-analogs of favanones. The β -lactam class of antibiotics is generally recognized to be a cornerstone of human health
care due to the unparalleled clinical efficacy and safety of this type of antibacterial compound. In addition to their biological
relevance as potential antibiotics, β-lactams have also acquired a prominent place in organic chemistry as synthons and provide
highly efficient routes to a variety of non-protein amino acids, such as oligopeptides, peptidomimetics, nitrogen-heterocycles,
as well as biologically active natural and unnatural products of medicinal interest such as indolizidine alkaloids, paclitaxel,
docetaxel, taxoids, cyptophycins, lankacidins etc. A straight forward route toward the synthesis of quinoline-4-ones via the
triflic acid assisted Fries rearrangement of N-aryl-β-lactams has been reported by Tepe and co-workers. The ring expansion
observed in this case was solely attributed to the inherent ring strain in β-lactam ring because β -lactam failed to undergo
rearrangement under reaction conditions. The above mentioned protocol has been recently extended by our group for the
synthesis of benzo [b]-azocinon-6-ones via a tandemMichael addition–Fries rearrangement of sorbyl anilides as well as for the
single-pot synthesis of 2-aryl-quinolin-4(3H)-ones through the Fries rearrangement of 3-dienyl-β-lactams. In continuation
with our synthetic endeavors with the β-lactam ring and in view of the lack of convenient approaches for the synthesis of
C-3 functionalized quinolin-4(1H)-ones, the present work describes the single-pot synthesis of C-3 functionalized quinolin-
4(1H)-ones via the triflic acid promoted Fries rearrangement of C-3 vinyl/isopropenyl substituted β -lactams. In addition, DFT
calculations and MD simulations were performed to investigate the stability profiles of synthetic compounds.