2002
DOI: 10.1002/jhet.5570390129
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Arenesulfonylheterocycles (I): Synthesis and reactions of 2‐benzenesulfonyl‐4,5‐dichloropyridazin‐3‐ones with amines

Abstract: The direct sulfonylation of 4,5‐dichloropyridazin‐3‐ones with some benzenesulfonyl chlorides in the presence of base in tetrahydrofuran gave only the corresponding N‐sulfonylated product. The reaction of 2‐benzenesulfonyl‐4,5‐dichloropyridazin‐3‐ones with some aliphatic amines under neutral conditions afforded 5‐alkylamino‐2‐benzenesulfonyl‐4‐chloropyridazin‐3‐ones and/or the corresponding N‐alkyl‐benzenesulfonamides.

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Cited by 22 publications
(3 citation statements)
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“…4,5-Dichloro-2-( p -nitrobenzenesulfonyl)­pyridazin-3­(2 H )-one ( 5 ) could be prepared by the reaction of 4,5-dichloropyridazin-3­(2 H )-one with p -nitrobenzenesulfonyl chloride in moderate to excellent yields (method C in Scheme ). 2-Nitro-4,5-disubstituted pyridazin-3­(2 H )-ones 6 were successfully synthesized through the reaction of the corresponding pyridazin-3­(2 H )-ones with Cu­(NO 3 ) 2 ·3H 2 O and acetic anhydride at room temperature in good to excellent yields (method D in Scheme ). Kim et al reported for the first time the preparation of 2-cyano-4,5-disubstituted pyridazin-3­(2 H )-ones 7 and utilized them for chemoselective electrophilic cyanation.…”
Section: Preparation Of 2-substituted 45-dichloropyridazin-3(2h)-onesmentioning
confidence: 99%
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“…4,5-Dichloro-2-( p -nitrobenzenesulfonyl)­pyridazin-3­(2 H )-one ( 5 ) could be prepared by the reaction of 4,5-dichloropyridazin-3­(2 H )-one with p -nitrobenzenesulfonyl chloride in moderate to excellent yields (method C in Scheme ). 2-Nitro-4,5-disubstituted pyridazin-3­(2 H )-ones 6 were successfully synthesized through the reaction of the corresponding pyridazin-3­(2 H )-ones with Cu­(NO 3 ) 2 ·3H 2 O and acetic anhydride at room temperature in good to excellent yields (method D in Scheme ). Kim et al reported for the first time the preparation of 2-cyano-4,5-disubstituted pyridazin-3­(2 H )-ones 7 and utilized them for chemoselective electrophilic cyanation.…”
Section: Preparation Of 2-substituted 45-dichloropyridazin-3(2h)-onesmentioning
confidence: 99%
“…N -Benzenesulfonylation of 1° and 2° amines with 2-benzenesulfonyl-4,5-dichloropyridazin-3­(2 H )-ones 5 has been reported . Compounds 5 have the sulfonyl-transfer potential over the nucleophiles such as 1° and 2° amines, carboxylates, and alkoxides.…”
Section: Pyridazin-3(2h)-ones As Recyclable Functional Group Carriersmentioning
confidence: 99%
“…The sub-models have a similar logical structure to the land use design process of Urban Land Use Planning [28,31]. In other words, the program structure is designed to first identify the location and area of developable land by usage, then to project the demand in a non-spatial manner by usage, and finally to allocate the demand to the lands deemed suitable for development [27,32].…”
Section: Introductionmentioning
confidence: 99%