Synthesis of Substituted Azepino[3,4‐b]indole‐1,5‐diones

Abstract

Cyclic β‐amino esters 4, obtained from lactams, were condensed with indole‐2‐carbonyl chloride to afford the corresponding amides. Similarly, unusual conditions led to cyclisation at the 3‐position of the indole moiety in the presence of pTSA and ethylene glycol to afford previously unknown pentacyclic derivatives 12 and 15. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

Identification of Mineralocorticoid Receptor Modulators with Low Impact on Electrolyte Homeostasis but Maintained Organ Protection

“…The first route started from commercially available substituted 4 H -1,4-benzoxazin-3-ones ( 54 ), which were tert -butoxycarbonyl (BOC)-protected to provide 55 . A tandem reduction/Horner–Wadsworth–Emmons/Michael addition reaction sequence provided 56 . Explicitly, treatment of 55 with LiBEt 3 H at −78 °C produced an intermediate hemiaminal, which was reacted further with the anion of triethyl phosphonoacetate in a highly efficient olefination reaction and the intermediate finally underwent a spontaneous intramolecular Michael addition to provide 3-substituted 3,4-dihydro-2 H -1,4-benzoxazines ( 56 ).…”

Environmentally Friendly Synthesis of Indoline Derivatives using Flow‐Chemistry Techniques

“…One of them involved N-protected aminophenyl derivatives containing ethyl but-2-enoates, from which target molecule 4 could be obtained by an aza-Michael reaction. [13][14][15] The other main possibility was the reduction of corresponding indole 3. According to the literature, 3 could be reduced by sodium [cyanotrihydridoborate(III)] [Na(CN)BH 3 ] in acetic acid [4,5] or with the borane trimethylamine complex (Me 3 N·BH 3 ) in highly acidic media (trifluoroacetic acid).…”