2011
DOI: 10.1002/chin.201110164
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ChemInform Abstract: Novel Regioselective Synthesis of 4‐Isothiocyanatobutan‐2‐one (III) by a Staudinger Reaction. Preparation of 6‐Unsubstituted 4‐Hydroxyhexahydropyrimidine‐2‐thiones.

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“…We hypothesized that -unsaturated aldehydes and ketones could be selectively transformed into respective β-isothiocyanato carbonyl compounds 1 and 3 by the addition of HN 3 to give -azido aldehydes and ketones [22,23] followed by transformation of the azido group into an isothiocyanato group using a Staudinger/aza-Wittig sequence [24][25][26][27][28][29][30]. In our preliminary communication, an example of the application of this methodology has been described [31]. Herein, we report full details of the selective synthesis of -unsubstituted isothiocyanato ketones from -unsaturated ketones.…”
Section: Methodsmentioning
confidence: 99%
“…We hypothesized that -unsaturated aldehydes and ketones could be selectively transformed into respective β-isothiocyanato carbonyl compounds 1 and 3 by the addition of HN 3 to give -azido aldehydes and ketones [22,23] followed by transformation of the azido group into an isothiocyanato group using a Staudinger/aza-Wittig sequence [24][25][26][27][28][29][30]. In our preliminary communication, an example of the application of this methodology has been described [31]. Herein, we report full details of the selective synthesis of -unsubstituted isothiocyanato ketones from -unsaturated ketones.…”
Section: Methodsmentioning
confidence: 99%