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Paper | Special issue | Vol 61, No. 1, 2003, pp.173-182
Published online, 10th June, 2003
DOI: 10.3987/COM-03-S12
Amine-induced Rearrangement of 4-Imino-4H-3,1-benzoxazines to 4-Quinazolinones via Amidine Carboxamides

Barry B. Snider* and Hongbo Zeng

*Department of Chemistry MS 015, Brandeis University, Waltham, MA 02454-9110, U.S.A.


Iminobenzoxazines (2) react with pyrrolidine in EtOAc at reflux to give amidine carboxamides (11), which cyclize to quinazolinones (3) on heating in 99:1 MeCN/HOAc. However, both amidines (11d) and (13d) are formed if R1 = Ar and R2 = Me. Hindered amidine (11f), R1 = Ph, R2 = i-Pr, does not cyclize to give quinazolinone (3f).