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Unconventional Alkoxylation of Pyrazino[2,3‐ c ][1,2,6]thiadiazine 2,2‐Dioxides Mediated by N ‐Halosuccinimides
Author(s) -
Campillo Nuria,
Páez Juan A.,
Goya Pilar
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200207)2002:13<2109::aid-ejoc2109>3.0.co;2-x
Subject(s) - chemistry , rationalization (economics) , reactivity (psychology) , computational chemistry , alcohol , medicinal chemistry , ab initio , organic chemistry , stereochemistry , medicine , philosophy , alternative medicine , epistemology , pathology
One pot alkoxylation at position 7 of 6‐arylpyrazino[2,3‐ c ][1,2,6]thiadiazine 2,2‐dioxides with NBS or NCS in the appropriate alcohol is described. Rationalization of the mechanism of the reaction, which does not proceed through the intermediate 7‐halo derivatives, is discussed on the basis of experimental reactivity and ab initio calculations. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)