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Ring Expansion of 2-Alkylidenedihydroquinazolines to Iminodihydro-1,4-benzodiazepines by Methanesulfonyl and Trifluoromethanesulfonyl Azide

✍ Scribed by Helmut Quast; Svetlana Ivanova; Eva-Maria Peters; Karl Peters

Book ID: 102657912
Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 685 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(200004)2000:8<1577::aid-ejoc1577>3.0.co;2-6

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✦ Synopsis

2-Alkyl-1-methylquinazolinium hexafluorophosphates 9 are deprotonated by sodium or potassium hydride to afford solutions of 2-alkylidenedihydroquinazolines 10, which were investigated by NMR spectroscopy. Trapping with methanesulfonyl azide (5a) of 10 in situ or subsequent treatment with trifluoromethanesulfonyl azide (5b) gives mixtures of colourless ( 15) and intensely yellow N-sulfonylimino-1,4-benzodiazepines 16 along with products due to cleavage of the exo-[

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