A Short-Cut to Substituted Fused Pyrrolo[2,1-c][1,4]oxazines: A Hybrid Theoretical and Experimental Study

被引：3
|
作者：
Ivanov, Andrey V. V. [1 ]
Bobkov, Alexander S. S. [2 ]
Martynovskaya, Svetlana V. V. [1 ]
Budaev, Arsalan B. B. [1 ]
Vitkovskaya, Nadezhda M. M. [2 ]
机构：
[1] Russian Acad Sci, Favorsky Irkutsk Inst Chem, Lab Heterocycl Cpds, Siberian Branch, 1 Favorsky St, Irkutsk 664033, Russia
[2] Irkutsk State Univ, Lab Quantum Chem Modeling Mol Syst, 1 Karl Marx St, Irkutsk 664003, Russia
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 12卷 / 08期
关键词：
pyrrolooxazines; allenes; quantum chemistry; reaction mechanisms; superbase;
D O I：
10.1002/ajoc.202300153
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The effect of substituents in the pyrrole ring and at the triple bond on the formation of fused pyrrolooxazines from 1H-pyrrol-2-ylmethanols and propargyl chlorides has been theoretically and experimentally studied. The energy characteristics of the reaction are evaluated using quantum-chemical calculations (CBS-Q//B3). A one-pot transition metal-free synthesis of substituted 3-methyl-1H-pyrrolo[2,1-c][1,4]oxazines in good yields has been implemented in the superbasic system NaOH/DMSO.
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页数：7
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