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- W2095758396 abstract "A facile stereoselective synthesis of Knoevenagel-type compounds 8 and 9 was accomplished through a one-pot two-step procedure. The reaction of ethylenethiourea ( 1) and ethyleneurea ( 2) with benzoyl chloride- N, N-dimethylformamide complex in N, N-dimethylformamide gave the corresponding isolable ternary N-methyleniminium chlorides 3 and 4, along with benzoic acid ( 5) as a byproduct. Hydrolysis of salts 3 and 4 yielded the N-formyl derivatives 6 and 7, thus confirming the N-methyleniminium structure. Salts 3 and 4 condensed in situ at 120 °C with a variety of acyclic active methylene reagents Y-CH 2 -Z (Y = or ≠ Z), in the presence of 5 (Procedure A) or of 5 and triethylamine (1.5 equiv) (Procedure B), afforded α,β-unsaturated compounds 8 and 9. The overall yields ranged from poor to good. Mechanistic hypotheses concerning the formation of 3 and 4 and the origin of the stereoselectivity are also discussed." @default.
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- W2095758396 date "2007-12-18" @default.
- W2095758396 modified "2023-09-24" @default.
- W2095758396 title "Unprecedented One-Pot Stereoselective Synthesis of Knoevenagel-Type Derivatives via in situ Condensation of N-Methyleniminium Salts of Ethylenethiourea and Ethyleneurea with Active Methylene Reagents." @default.
- W2095758396 cites W2952101186 @default.
- W2095758396 doi "https://doi.org/10.1002/chin.200751163" @default.
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