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Literature DB >> 12153197

Type 2 intramolecular N-acylnitroso diels-alder reaction: stereoselective synthesis of bridged bicyclic oxazinolactams.

Chun P Chow¹, Kenneth J Shea, Steven M Sparks.

Abstract

[reaction: see text] The type 2 intramolecular N-acylnitroso Diels-Alder reaction has been employed for the synthesis of substituted bridged bicyclic oxazinolactams. Upon oxidation of hydroxamic acid 6, a 3-benzylated oxazinolactam (7) was synthesized with complete diastereoselectivity. Elaboration of cycloadduct 7 liberated a cis-3,7-disubstituted azocin-2-one (9).

Entities: Chemical

Mesh：

Substances：
Lactams
Nitroso Compounds

Year: 2002 PMID： 12153197 DOI： 10.1021/ol026075k

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

Keyword Cloud
Cited

6 in total

1. Type 2 intramolecular N-acylazo Diels-Alder reaction: regio- and stereoselective synthesis of bridgehead bicyclic 1,2-diazines.

Authors: Claudia L Molina; Chun P Chow; Kenneth J Shea
Journal: J Org Chem Date: 2007-08-04 Impact factor: 4.354

2. Nitrenium ion azaspirocyclization-spirodienone cleavage: a new synthetic strategy for the stereocontrolled preparation of highly substituted lactams and N-hydroxy lactams.

Authors: Duncan J Wardrop; Matthew S Burge
Journal: J Org Chem Date: 2005-12-09 Impact factor: 4.354

6. #Nitrosocarbonyls 1: antiviral activity of N-(4-hydroxycyclohex-2-en-1-yl)quinoline-2-carboxamide against the influenza A virus H1N1.

Authors: Dalya Al-Saad; Misal Giuseppe Memeo; Paolo Quadrelli
Journal: ScientificWorldJournal Date: 2014-12-31

6 in total

Type 2 intramolecular N-acylnitroso diels-alder reaction: stereoselective synthesis of bridged bicyclic oxazinolactams.

1. Type 2 intramolecular N-acylazo Diels-Alder reaction: regio- and stereoselective synthesis of bridgehead bicyclic 1,2-diazines.

2. Nitrenium ion azaspirocyclization-spirodienone cleavage: a new synthetic strategy for the stereocontrolled preparation of highly substituted lactams and N-hydroxy lactams.

Review 3. Chemistry of bridged lactams and related heterocycles.

Review 4. The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.

5. Stability of medium-bridged twisted amides in aqueous solutions.

6. #Nitrosocarbonyls 1: antiviral activity of N-(4-hydroxycyclohex-2-en-1-yl)quinoline-2-carboxamide against the influenza A virus H1N1.