desensitization55-58 was isolated in 80% yield under our reaction
conditions. 5d as a high blood pressure regulator which is
commercially available by Merck was obtained in 63% yield
using of methanol as solvent59. Quinazoline compounds such as
5g and 5h were successfully obtained under the reaction
conditions (Table 4).
Acknowledgments
We thank the financial support from the National Natural
Science Foundation of China (No. 21402088, No. 21472082 and
No. 21473092). The Natural Science Foundation of Jiangsu
Province (NO. BK20170939), the Natural Science Foundation of
the Jiangsu Higher Education Institutions of China (No.
17KJB150016 and No. 17KJB610006), the Basic Research
Program of Shenzhen (JCYJ20170818161714678), the SIAT
Innovation Program for Excellent Young Researchers (2017014)
and Shenzhen Peacock Plan, the Startup Foundation for
Introducing Talent of NUIST (NO. 2016r044), the Jiangsu
Province joint research project (No. BY2014007-01) and SIAT
Innovation Program for Excellent Young Researchers (2017014)
are acknowledgement.
References and notes
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Scheme 2. Proposal mechanism for the oxidative process
Based on the above control experiments, the reaction
mechanism of this metal free oxidative process was proposed in
Scheme 2. The heating of tert-butyl hydroperoxide resulted in the
formation of hydroxyl radicals and tert-butanol radicals.
Hydrogen atom transfer between tert-butanol radical and
phenylmethanol gave α-hydroxyl- carbon radical, then the radical
cross coupling of hydroxyl radical and carbon radical gave an
unstable phenylmethanediol intermediate then gave the
benzaldehyde by an elimination reaction of water, which
underwent the unknown reaction pathway leading to the
quinazolinones, benzothiadiazines and quinazolines formation.
Conclusion
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Good
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compatibility, metal free conditions and various primary alcohols
all tolerant enable the present method to be great valuable in
organic synthesis.