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Synlett 2018; 29(01): 116-120
DOI: 10.1055/s-0036-1588549
DOI: 10.1055/s-0036-1588549
letter
Iodine-Catalyzed Regioselective Sulfenylation of 4H-Pyrido[1,2-a]pyrimidin-4-ones with Sulfonyl Hydrazides
Authors
The work was financially supported by the Project for Enhanced Innovation of Guangdong Pharmaceutical University, Provincial Experimental Teaching Demonstration Center of Chemistry and Chemical Engineering.
Weitere Informationen
Publikationsverlauf
Received: 16. Juni 2017
Accepted after revision: 18. Juli 2017
Publikationsdatum:
22. August 2017 (online)
Abstract
A simple and efficient method for direct sulfenylation of 4H-pyrido[1,2-a]pyrimidin-4-ones with sulfonyl hydrazides has been developed. The transformation is catalyzed by iodine under metal-free conditions with high regioselectivity and good functional-group tolerance.
Key words
sulfenylation - pyridopyrimidinones - sulfonyl hydrazides - iodine catalysis - regioselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588549.
- Supporting Information (PDF)
-
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3-(Phenylsulfanyl)-4H-pyrido[1,2-a]pyrimidin-4-one (3a); Typical Procedure
1a (29 mg, 0.2 mmol), PhSO2NHNH2 (2a; 41 mg, 0.24 mmol), I2 (10mg, 20 mol%), and EtOH (0.5 mL) were stirred in a sealed tube at 100 °C for 12 h. When the reaction was complete (TLC), EtOAc (10 mL) was added. The organic phase was washed with brine (2 × 3 mL) and dried (Na2SO4). The solvent was removed, and the crude product was separated by column chromatography [silica gel, PE–EtOAc (3:1)] to give a white solid; yield: 40 mg (78%); mp 106–108 °C. 1H NMR (400 MHz, CDCl3): δ = 9.09 (d, J = 7.2 Hz, 1 H), 8.46 (s, 1 H), 7.80–7.76 (m, 1 H), 7.69 (m, 1 H), 7.39 (m, 2 H), 7.30–7.27 (m, 2 H), 7.24–7.19 (m, 2 H). 13C NMR (100 MHz, CDCl3): δ = 157.5, 156.7, 151.3, 136.4, 134.5, 130.1, 129.2, 127.7, 127.1, 126.7, 116.4, 111.6. ESI-MS: m/z = 255 [M + H]+. HRMS (ESI): m/z [M + H]+ calcd for C14H11N2OS: 255.0593; found: 255.0597. Anal. Calcd C, 66.12; H, 3.96; N, 11.02. Found: C, 66.03; H, 3.91; N, 10.90.