期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 71, 期 1, 页码 185-193出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo051832o
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资金
- NCI NIH HHS [CA42056, R01 CA042056-21, R01 CA042056] Funding Source: Medline
Two new unsymmetrical 1,2,4,5-tetrazines, 3-methylsulfinyl-6-methylthio-1,2,4,5-tetrazine (4) and 3-(benzyloxycarbonyl)amino-6-methylsulfinyl-1,2,4,5-tetrazine (5), were prepared, and the scope of their participation in intermolecular inverse electron demand Diels-Alder reactions was defined. As anticipated, sulfoxides 4 and 5 (4 > 5) display a reactivity that is substantially greater than that of their corresponding sulfides (2 and 3), being derived from their enhanced electron-deficient character and resulting in a wider range of potential dienophile choices or the use of milder reaction conditions. The cycloaddition reactions were expectedly regioselective, typically producing a single cycloadduct, ensuring their synthetic utility, but both were found to proceed with a regio selectivity opposite what would be anticipated and complementary to that observed with 2 and 3.
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