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Application of Furan as a Diene: Preparation of Condensed 1,3‐Oxazines by Retro‐Diels−Alder Reactions
Author(s) -
Stájer Géza,
Miklós Ferenc,
Kanizsai Iván,
Csende Ferenc,
Sillanpää Reijo,
Sohár Pál
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400247
Subject(s) - chemistry , furan , chlorobenzene , diels–alder reaction , benzoic acid , diene , oxazines , organic chemistry , methanol , medicinal chemistry , catalysis , natural rubber
(Di‐ exo ‐3‐amino‐7‐oxabicyclo[2.2.1]hept‐5‐en‐2‐yl)methanol ( 3 ) was treated with oxo carboxylic acids [ p ‐toluoylpropionic acid, cis ‐ or trans ‐( p ‐toluoyl)cyclohexanecarboxylic acid, ‐benzoic acid or methanobenzocyclooctenecarboxylic acid] to furnish the oxanorbornene‐fused pyrrolo[1,3]oxazine 4, the isoindolo[1,3]oxazines 5 and 6 , and the methanobenzocyclooctenepyrrolo[1,3]oxazine 10 , together with the retro‐Diels−Alder products pyrrolooxazinone 7 , oxazinoisoindolones 8 and 9 , and oxazinopyrrolobenzocyclooctene 11 . On reflux in chlorobenzene, furan was released from the oxanorbornene heterocycles 5 and 10 to give the retro‐Diels−Alder products. The structures of the new compounds were established by NMR spectroscopy and also (for 6 and 9 ) by single‐crystal X‐ray structure determination. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)