✦ LIBER ✦

Synthesis of 2-(α-Substituted N-Tosylaminomethyl)-2,5-Dihydrofurans by Reaction of N-Sulfonylimines with Arsonium or Sulfonium 4-Hydroxyl-cis-2-butenylides

✍ Scribed by Wei-Ping Deng; An-Hu Li; Li-Xin Dai; Xue-Long Hou

Book ID: 104202623
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 224 KB
Volume: 56
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(00)00191-5

No coin nor oath required. For personal study only.

✦ Synopsis

AbstractÐOn treatment of N-tosylimines 1 and 4-hydroxyl-cis-butenyl arsonium salt 5 or sulfonium salt 11a with KOH in acetonitrile at room temperature, 2-(a-substituted N-tosylaminomethyl)-2,5-dihydrofurans 4 were obtained in moderate yields through a new ylide cyclization process. Ylide 2 acts formally as an equivalent of the 2,5-dihydrofuran anion. However, the reaction of 4-hydroxyl-trans-butenyl sulfonium salt 11b with N-tosylimine 1b under the same conditions gave only the normal aziridination product 12. A plausible mechanism was proposed for this new 5-membered cyclization reaction, and a high yield process for the synthesis of target molecules 4 is also recommended.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of 2-(α-S

ChemInform Abstract: Synthesis of 2-(α-Substituted N-Tosylaminomethyl)-2,5-dihydrofurans by Reaction of N-Sulfonylimines with Arsonium or Sulfonium 4-Hydroxy-cis-2-butenylides.

✍ Wei-Ping Deng; An-Hu Li; Li-Xin Dai; Xue-Long Hou 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 1 views

A straight synthesis of 2–(α-substituted

A straight synthesis of 2–(α-substituted N-tosylaminomethyl)-2,5-dihydrofurans by the reaction of N-sulfonylimines with arsonium 4-hydroxyl- cis -2-butenylides

✍ An-Hu Li; Wei-Ping Deng; Li-Xin Dai; Xue-Long Hou 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 English ⚖ 224 KB

Reaction of substituted sulfenes with N,

Reaction of substituted sulfenes with N,N-disubstituted α-amino-methyleneketones. I. Synthesis of N,N-disubstituted cis- and trans-4-amino-3,4,5,6,7,8-hexahydro-3-phenyl-1,2-benzoxathiin 2,2-dioxides

✍ Alberto Bargagna; Gaetano Bignardi; Pietro Schenone; Mario Longobardi 📂 Article 📅 1983 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 260 KB

Reaction of substituted sulfenes with N,

Reaction of substituted sulfenes with N,N-disubstituted α-amino-methyleneketones. II. Synthesis of N,N-disubstituted cis and trans 4-amino-3-chloro-3,4,5,6,7,8-hexahydro-1,2-benzoxathiin 2,2-dioxides, and 4-amino-5,6,7,8-tetrahydro-1,2-benzoxathiin 2,2-dioxides

✍ Alberto Bargagna; Pietro Schenone; Gaetano Bignardi; Mario Longobardi 📂 Article 📅 1983 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 216 KB

Synthesis of Novel 2,3-Substituted Quina

Synthesis of Novel 2,3-Substituted Quinazolin-4-ones by Condensation of Alkyl or Aromatic Diamines with 5-(N-Arylimino)-4-chloro-5H-1,2,3-dithiazoles.

✍ Maria de Fatima Pereira; Valerie Thiery; Thierry Besson 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 27 KB 👁 2 views

Synthesis by the Arbuzov-like dealkylati

Synthesis by the Arbuzov-like dealkylation reaction, characterization, and reactivity of phosphonate and amino-substituted phosphonate ruthenium complexes, [(η5-C5H5)(CO)2Ru{P(O)(OR)n(NC4H8) 2−n}] (n = 0–2), and comparison with the iron analogues

✍ Hiroshi Nakazawa; Toshiyuki Fujita; Kazuyuki Kubo; Katsuhiko Miyoshi 📂 Article 📅 1994 🏛 Elsevier Science 🌐 English ⚖ 948 KB