Premium
Unusual Pericyclic Reactivity of 4‐Nitrobenzofuroxans in 1,3‐Dipolar Cycloaddition with N‐Benzyl Azomethine Ylide – A New Example of Multiple C–C‐Bond Forming Transformations.
Author(s) -
Starosotnikov Alexey M.,
Bastrakov Maxim A.,
Kachala Vadim V.,
Fedyanin Ivan V.,
Shevelev Svyatoslav A.,
Dalinger Igor L.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201802117
Subject(s) - azomethine ylide , cycloaddition , pericyclic reaction , substituent , pyrrolidine , chemistry , reactivity (psychology) , ring (chemistry) , 1,3 dipolar cycloaddition , ylide , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
A series of 4‐nitrobenzofuroxans were examined in [3+2]‐cycloaddition reactions with N‐benzyl azomethine ylide. The reaction outcome was found to be dependent on the nature of substituent 7‐R: for R=H and SR’ the products of double cycloaddition of the dipole were isolated, whereas for R=CH 3 , OR’ and NR'R” tetrahydroisoindoles annelated with furoxan ring were the sole products. As a result efficient chemoselective method for the synthesis of mono‐ and bis‐pyrrolidine fused benzofuroxan derivatives was developed.