Sulfonyl‐Activated Cyclobutenes as Building Blocks for the Synthesis of Dihydrodiazepines | Zendy

Landen Harald | Zendy; Martin HansDieter | Zendy; Steigel Alois | Zendy

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Sulfonyl‐Activated Cyclobutenes as Building Blocks for the Synthesis of Dihydrodiazepines

Author(s) -

Landen Harald,

Martin HansDieter,

Steigel Alois

Publication year - 1987

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19871200208

Subject(s) - sulfone , chemistry , sulfoxide , cyclobutene , regioselectivity , yield (engineering) , reactivity (psychology) , sodium periodate , sulfonyl , medicinal chemistry , organic chemistry , catalysis , ring (chemistry) , medicine , materials science , alternative medicine , alkyl , pathology , metallurgy

1,2‐Bis(phenylthio)‐1‐cyclobutene ( 5 ), prepared in high yield using a modified literature procedure, was oxidized to the corresponding bis‐sulfone 2 , sulfone‐sulfoxide 9 , bis‐sulfoxide 10 , or monosulfoxide 15 by means of hydrogen peroxide or sodium periodate, respectively. When treated with diazomethane the bis‐sulfone 2 and the sulfone‐sulfoxide 9 yield the dihydrodiazepines 4a and 11 , respectively. The reactivity of these cyclobutenes and the regioselectivity of 9 is discussed in terms of the MNDO model.

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