Mesoionische Sechsringheterocyclen, V [1, 2]; Reaktionen von 6-Oxo-6H-1.3-oxazin-3-ium-4-olaten mit o-Chinonen und Heterokumulenen / Mesoionic Six-Membered Heterocycles, V [1, 2] Reactions of 6-Oxo-6H-l,3-oxazin-3-ium-4-olates with o-Quinones and Heterocumulenes

Author:

Friedrichsen Willy1,Kujath Eckard1,Liebezeit Gerd1

Affiliation:

1. Institut für Organische Chemie der Universität Kiel, Olshausenstraße 40-60, D-2300 Kiel

Abstract

Abstract Mesoionic 6-oxo-6H-1,3-oxazine-3-ium-4-olates (1, 7) react with o-quinones (2, 4) to give compounds 3, 6, which may result from a primary [4+4]cycloaddition and subsequent loss of carbon dioxide. Phenyl isocyanate and phenylisothiocyanate react with 1h and 9 - possibly via a [2 + 4]cycloadduct - to give 11, 12, 13 and 14, respectively

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

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1. Computational Screening of New Orthogonal Metal‐Free Dipolar Cycloadditions of Mesomeric Betaines;Chemistry – A European Journal;2018-04-27

2. Reactions of Arylpropynehydrazides with Substituted Malonyl Chlorides: A Route to Pyrazolo-Condensed 1,3-Oxazines;European Journal of Organic Chemistry;2012-05-03

3. Heterocycle-Forming Reactions of 1,2-Benzoquinones;Advances in Heterocyclic Chemistry Volume 100;2010

4. (Chlorocarbonyl)ethylketene;Encyclopedia of Reagents for Organic Synthesis;2001-04-15

5. Chemistry of Pyrido [2,1-b] [1,3] oxazines, Pyrido[2,1-b] [1,3] thiazines, and Their Benzologs, Part IV;Advances in Heterocyclic Chemistry Volume 72;1998

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