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.

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. Full article

Journal

ChemistrySelect
ISSN: 2365-6549

Output data

Year: 2018, Volume: 3, Number: 34, Pages: 9773-9777 Pages count : 5 DOI: 10.1002/slct.201802117

Authors

Starosotnikov Alexey M. ¹ , Bastrakov Maxim A. ¹ , Kachala Vadim V. ¹ , Fedyanin Ivan V. ² , Shevelev Svyatoslav A. ¹ , Dalinger Igor L. ¹

Affiliations

1	N.D.Zelinsky Institute of Organic Chemistry RAS, Leninsky prosp. 47, Moscow, 119991 Russia
2	A.N. Nesmeyanov Institute of Organoelement Compounds RAS, Vavilova str. 28, Moscow, 119991 Russia

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=CH3, 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.

Starosotnikov A.M. , Bastrakov M.A. , Kachala V.V. , Fedyanin I.V. , Shevelev S.A. , Dalinger I.L.
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.
ChemistrySelect. 2018. V.3. N34. P.9773-9777. DOI: 10.1002/slct.201802117 WOS Scopus OpenAlex

Web of science:	WOS:000444538800002
Scopus:	2-s2.0-85053418264
OpenAlex:	W2891749344

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