Synlett 2024; 35(16): 1877-1882
An Efficient Access to Heteroaryl/Aryl-Annulated Pyridine Derivatives and a Study of Their Mosquito Larvicidal Activity Against Dengue Vector
Pamela Pal‡
a
Department of Chemistry, Diamond Harbour Women’s University, Sarisha-743368, West Bengal, India
,
Sayanti Show‡
a
Department of Chemistry, Diamond Harbour Women’s University, Sarisha-743368, West Bengal, India
,
Sukanya Das
b
Department of Chemistry, Jadavpur University, Kolkata-700032, West Bengal, India
,
Sayantika Bhakta
c
Department of Applied Chemistry, Maulana Abul Kalam Azad University of Technology, Haringhata, West Bengal, India
,
Swarupa Mondal
d
Department of Zoology, Diamond Harbour Women’s University, Sarisha-743368, West Bengal, India
,
Priya Roy∗
d
Department of Zoology, Diamond Harbour Women’s University, Sarisha-743368, West Bengal, India
,
Tapas Ghosh∗
b
Department of Chemistry, Jadavpur University, Kolkata-700032, West Bengal, India
c
Department of Applied Chemistry, Maulana Abul Kalam Azad University of Technology, Haringhata, West Bengal, India
,
a
Department of Chemistry, Diamond Harbour Women’s University, Sarisha-743368, West Bengal, India
b
Department of Chemistry, Jadavpur University, Kolkata-700032, West Bengal, India
› Author Affiliations This work is supported by UGC through a startup grant (No. F.30-567/2021-BSR). S.D. thanks DST INSPIRE for her Ph.D. fellowship (IF 190973).
Dedicated to Professor K. C. Majumdar on his 78th birthday
Abstract
We report a convergent synthesis of heteroaryl/aryl-annulated pyridine and quinoline derivatives by a metal-free Povarov reaction. para -Toluene sulfonic acid was used as the catalyst in this reaction, which produced the products in good yields from the corresponding aromatic amines and ethyl vinyl ether. A pyridocoumarin and a pyridopyrimidine product were evaluated for their mosquito larvicidal activity against the third instar larvae of the dengue vector mosquito Aedes aegypti . Examination of morphological changes in the larvae showed damage to the target body part after treatment with both the pyridocoumarin and pyridopyrimidine products at the LC50 concentrations.
Key words
pyridocoumarins -
pyridopyrimidines -
Povarov reaction -
metal-free synthesis -
insecticides
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/a-2251-1849.
Supporting Information
Publication History
Received: 22 January 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
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1,3,6-Trimethylpyrido[3,2-d ]pyrimidine-2,4(1H ,3H )-dione (3a); Typical Procedure
A mixture of compound 1a (0.100 g, 0.64 mmol) and ethyl vinyl ether (2 ; 0.139 g, 1.93 mmol) in DMSO (5 mL) was stirred for 5 min at r.t. PTSA (11 mg, 0.0645 mmol) was added, and the mixture was stirred at r.t. for another 30 min. The mixture was then heated at 80 °C for 2 h, until the starting material disappeared (Confirmed by TLC). The mixture was then allowed to cool at r.t., worked up in H2 O, and extracted with EtOAc (3 × 10 mL). The combined organic layer washed with brine, dried (Na2 SO4 ), filtered, and evaporated to dryness. The crude product was purified by column chromatography [silica gel, PE–EtOAc (7:3)] to give an off-white solid; yield: 0.112 g (0.546 mmol, 88%); mp 121–124 °C.
IR AT-IR (Neat): 1704, 1661, 1607, 1574, 1498, 1315, 749 cm –1 . 1 H NMR (400 MHz, CDCl3 ): δ = 2.70 (s, 3 H, –CH3 ), 3.54 (s, 3 H, –NCH3 ), 3.60 (s, 3 H, –NCH3 ), 7.45–7.54 (m, 2 H, ArH). 13 C NMR (100 MHz, CDCl3 ): δ = 23.9, 28.9, 30.5, 122.3, 128.7, 131.3, 135.8, 150.5, 154.5, 160.6. HRMS (ESI): m/z [M + H]+ calcd for C10 H12 N3 O2 : 206.0930; found: 206.0927.
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