Facile Access to Bicyclic Sultams with Methyl 1‐Sulfonylcyclopropane‐1‐carboxylate Moieties | Zendy

Rassadin Valentin A. | Zendy; Tomashevskiy Aleksandr A. | Zendy; Sokolov Viktor V. | Zendy; Ringe Arne | Zendy; Magull Jörg | Zendy; de Meijere Armin | Zendy

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Facile Access to Bicyclic Sultams with Methyl 1‐Sulfonylcyclopropane‐1‐carboxylate Moieties

Author(s) -

Rassadin Valentin A.,

Tomashevskiy Aleksandr A.,

Sokolov Viktor V.,

Ringe Arne,

Magull Jörg,

de Meijere Armin

Publication year - 2009

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200900113

Subject(s) - chemistry , substituent , cerium , carboxylate , halogenation , bicyclic molecule , potassium carbonate , yield (engineering) , ceric ammonium nitrate , medicinal chemistry , organic chemistry , salt (chemistry) , aryl , alkyl , materials science , metallurgy , grafting , polymer

N ‐(2,3‐Dibromopropyl)‐ and N ‐(3,4‐dibromobutyl)(methoxycarbonyl)methanesulfanilides upon treatment with potassium carbonate in DMF furnish methyl 3‐aryl‐2,2‐dioxo‐2‐thia‐3‐azabicyclo[ n .1.0]alkane‐1‐carboxylates in yields ranging from 54 to 84 % (10 examples). The starting materials were obtained by sulfonylation of N ‐alkenylanilines with methyl (chlorosulfonyl)acetate and subsequent bromination. For the N ‐alkenylanilines (10 examples, 60–77 % yield) an efficient new synthesis employing a 2‐nitrophenylsulfonyl substituent as a protective as well as an activating group has been developed. The 4‐methoxyphenyl (PMP) group could easily be removed from the sultam nitrogen atom by treatment with cerium(IV) ammonium nitrate.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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