𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Regioselective reactions of mesyloxymethylazetidinones with nucleophiles I. Cleavage of the azetidinone ring, azetidinone-aziridine ring transformations

✍ Scribed by Éva Boros; Ferenc Bertha; József Fetter; Gábor Czira; Antal Feller; Gyula Simig; Mária Kajtár-Peredy

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
148 KB
Volume
43
Category
Article
ISSN
0022-152X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

magnified image

The reaction of 4‐mesyloxymethylazetidin‐2‐one derivatives 3 with ammonia and sodium methoxide was investigated. The two electrophilic centers of the substrate reactesuccessively, resulting in cleavage of the lactam bond and formation of a new aziridine ring. The resulting type 6 and 8 aziridinylacetic acid derivatives are related to the novel 2‐(aziridin‐2‐yl)‐3‐phenylpropionic acid type carboxypeptidase A inhibitors and, as such, potential drug candidates.

📜 SIMILAR VOLUMES

ChemInform Abstract: Regioselective Nucl
ChemInform Abstract: Regioselective Nucleophilic Ring Opening Reactions of 2,2- Disubstituted Aziridines - The Asymmetric Synthesis of α,α- Disubstituted Amino Acids.
✍ B. G. M. BURGAUD; D. C. HORWELL; A. PADOVA; M. C. PRITCHARD 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 36 KB 👁 1 views

Regioselective Nucleophilic Ring Opening Reactions of 2,2-Disubstituted Aziridines -The Asymmetric Synthesis of α,α-Disubstituted Amino Acids. -It is shown that, under appropriate conditions, 2,2disubstituted aziridines like (I) and (V) undergo regioselective ring opening reactions at C-3 with carb

ChemInform Abstract: An Elegant Approach
ChemInform Abstract: An Elegant Approach Towards the Regioselective Synthesis of Deazalumazines Through Nucleophile-Induced Ring Transformation Reactions of 6-Aryl-3-cyano-4-methylthio-2H-pyran-2-ones.
✍ Pratibha Srivastava; Abhishek S. Saxena; Vishnu J. Ram 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 28 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

ChemInform Abstract: Reactions of 1,2,4-
ChemInform Abstract: Reactions of 1,2,4-Triazines with Nucleophiles. Part 6. Use of SnH Methodology for the Direct Introduction of Cyclic Diketone Residue into the 1,2,4-Triazine Ring.
✍ D. N. Kozhevnikov; I. S. Kovalev; V. L. Rusinov; O. N. Chupakhin 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v