Facile synthesis of reactive benzoazetinone by flash vacuum pyrolysis of isatoic anhydride

Authors
Chiu, SJ Chou, CH
Citation
Sj. Chiu et Ch. Chou, Facile synthesis of reactive benzoazetinone by flash vacuum pyrolysis of isatoic anhydride, TETRAHEDR L, 40(52), 1999, pp. 9271-9272
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
52
Year of publication
1999
Pages
9271 - 9272
Database
ISI
SICI code
0040-4039(199912)40:52<9271:FSORBB>2.0.ZU;2-6
Abstract
Pyrolysis of isatoic anhydride (3) at 550 degrees C and ca. 1 x 10(-2) torr gave benzoazetinone (1, 80%) as the only product. The existence of 1 was c onfirmed by low-temperature NMR spectroscopy at -90 degrees C. Above -20 de grees C, 1 was converted to dimer (4, 50%), trimer (5, 22%), and anthranili c acid (6, 12%). Pyrolysis of 3 at 800 degrees C and ca. 1 x 10(-2) torr ga ve 1-cyanocyclopentadiene (7) in 38% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.