Tetracyclic systems: Synthesis of isoindolo[1,2‐b]thieno‐[2,3(3,2 or 3,4)‐e][1,3]thiazocines and Isoindolo[2,1‐a]thieno‐[2,3(3,2 or 3,4)‐f][1,4] and [1,5]diazocines

Abstract

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α-Hydroxylactams as Efficient Entries to Diversely Functionalized Ferrociphenols: Synthesis and Antiproliferative Activity Studies

“…We previously used ketone reduction to methylene group by triethylsilane and TFA (reaction iv in Scheme 1 ) for purely organic compounds that were complete in less than 1 day with a good yield (ca. 75%) [ 22 ]. Conversely, even if the ketone reduction in compounds 2B – D was selective, since the carbonyl groups of imides were unaffected, the reaction was very slow and incomplete even after 2 weeks.…”

The covalent reactivity of functionalized 5-hydroxy-butyrolactams is the basis for targeting of fatty acid binding protein 5 (FABP5) by the neurotrophic agent MT-21

“…Furthermore, we speculated that such reactivity might, at least in part, determine the biological activities of AHPO-containing compounds. Specifically, we envisioned that reversible iminium ion formation could directly mediate reaction with biological nucleophiles 40,41 or, alternatively, the iminium intermediate could undergo tautomerization in situ to form an extended Michael acceptor 42 (Fig. 1b).…”

Facile assembly of 1,5-diazocan-2-ones via cyclization of tethered sulfonamides to cyclopropenes

“…5,6 It is known that medium-sized 8-membered rings are difficult to assemble via conventional methods of cyclization, 7 largely due to the enthalpic cost incurred in the transition state as well as the decreased entropy of the cyclic products relative to their linear precursors. 8 Several alternative synthetic approaches to the eight-membered 1,5-diazocin-2-one core have been developed, including Beckman rearrangement, 9 fragmentation of 1,5-diazabicyclo[3.3.1]nonan-2-ones, 10 reductive N-N scission of tetrahydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-ones, [11][12][13][14] as well as various ring closures, exploiting intramolecular versions of reductive amination, [15][16][17][18] amine acylation, 7,[19][20][21][22] strain release-driven transamidation, [23][24][25] and S N Ar reactions. 26 Herein, we disclose a new application of metal-templated intramolecular 8-exo-trig cyclization involving nucleophilic addition of sulfonamides tethered to a cyclopropene moiety.…”