Synlett 2012; 23(17): 2526-2530
DOI: 10.1055/s-0032-1317181
letter
© Georg Thieme Verlag Stuttgart · New York

Chemo- and Regioselective 4CR Synthesis of Oxathiaaza[3.3.3]propellanes via Sequential C–S, C–N and C–O Bond Formation in a Single Pot

Atieh Rezvanian
a   Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran   Fax: +98(21)88006544   eMail: abdol_alizad@yahoo.com   eMail: aalizadeh@modares.ac.ir
,
Abdolali Alizadeh*
a   Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran   Fax: +98(21)88006544   eMail: abdol_alizad@yahoo.com   eMail: aalizadeh@modares.ac.ir
,
Long-Guan Zhu
b   Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 23. Juli 2012

Accepted after revision: 14. August 2012

Publikationsdatum:
21. September 2012 (online)


Zoom Image

Abstract

Oxathiaaza[3.3.3]propellane derivatives were prepared by reaction of in situ generated asymmetric thioureas with inter­mediate Knoevenagel adducts resulting from ninhydrin and malononitrile. This four-component sequential transformation performed in one reaction flask represents a general route to this unexplored valuable class of sulfur–nitrogen heterocycles. The chemoselectivity and regiochemistry of the products were established by IR, NMR and single crystal X-ray analysis.

Supporting Information