✦ LIBER ✦

Transformation of 5-Hydroxy- to (5-Chloropentanoyl)amino Derivatives under ‘Direct Amide Cyclization’ Conditions

✍ Scribed by Boyan Iliev; Sanjiv Verma; Anthony Linden; Heinz Heimgartner

Book ID: 102253329
Publisher: John Wiley and Sons
Year: 2006
Tongue: German
Weight: 114 KB
Volume: 89
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200690038

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The application of the ‘direct amide cyclization’ conditions to the linear δ‐hydroxy diamide 11 is described (Scheme 3). Instead of the cyclization to the expected nine‐membered cyclodepsipeptide, only the chloro acid 12 was obtained. Its formation could be explained by consecutive formation of the 1,3‐oxazol‐5(4__H__)‐one 16 and the six‐membered imino lactone 17 as intermediates (Scheme 4). The spontaneous isomerization of the latter gave 12 in a good yield.

📜 SIMILAR VOLUMES

Conversion of 4-methoxy-5-amino-6-mercap

Conversion of 4-methoxy-5-amino-6-mercaptopyrimidine sulfides under diazotization conditions to 1,2,3-triazole derivatives

✍ M. P. Nemeryuk; A. L. Sedov; I. Krzhepelka; T. S. Safonova 📂 Article 📅 1982 🏛 Springer US 🌐 English ⚖ 56 KB

Silica-Supported 2,4,6-Trichloro-1,3,5-t

Silica-Supported 2,4,6-Trichloro-1,3,5-triazine as an Efficient Reagent for Direct Conversion of Carboxylic Acids to Amides Under Solvent-Free Conditions

✍ Khalafi-Nezhad, Ali; Zare, Abdolkarim; Parhami, Abolfath; Rad, Mohammad Navid So 📂 Article 📅 2007 🏛 Taylor and Francis Group 🌐 English ⚖ 106 KB

Catalytic Activity of 1,3-Dibromo-5,5-di

Catalytic Activity of 1,3-Dibromo-5,5-dimethylhydantoin (DBH) in the One-Pot Transformation of N-Arylglycines to N-Arylsydnones in the Presence of NaNO2/Ac2O under Neutral Conditions: Subsequent Bromination of these Sydnones to Their 4-Bromo Derivatives.

✍ Davood Azarifar; Hassan Ghasemnejad-Bosra 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 18 KB 👁 2 views