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Synthesis and activities of tricyclic pyrido[3,4-g]quinazolines, pyrazolo[3,4-g]quinoxalines and pyrroloindazole regioisomers

“…In 2000, V. M. Lyubchanskaya et al reported the synthesis of 1,4-dihydropyrrolo[2,3-e]indazoles via a Nenitzescu indole synthesis from quinone derivatives 32 and enamines 33 (Scheme 5). 23 Cyclization to the corresponding furo[2,3-e]indazoles was also observed, but was reduced when enamino esters (33, R 2 = OEt) substituted at the nitrogen atom with a methyl or a benzyl group (R 1 = CH 3 or Bn) were used. Scheme 5.…”

“…Synthesis of tricyclic pyrazolo[3,4-g]quinoxalines 16,17, 13,14 21 16 and 22-24. 17,18 High yielding access to diversely substituted analogues (22)(23)(24) was described by Linsdley's group using microwave irradiation. Compound 24 was reported as a submicromolar allosteric inhibitor of Akt (protein kinase B/PKB) (Scheme 3).…”

An expedient general synthesis of pyrrolo[3,2-e]indazoles: domino Sonogashira/Cacchi coupling-heteroannulation reactions

“…The extant literature on the synthesis and bioactivity of pyrroloindazoles revealed that eight isomeric classes of pyrroloindazoles have so far been synthesised. [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33] Of these, only the [2,3-g]-isomers [18][19][20][21][22][23][24][25][26][27] and the [3,2-e]-isomers 22,24,25 display various biological activities. Thus, the [2,3-g]-isomers 1-4 and the [3,2-e]-pyrroloindazole 5 were bioactive.…”

Synthesis of new carbamate derivatives of indole and their modification

“…Neniţsescu reaction provides one of the most important methods for the synthesis of 5-hydroxyindols [10][11][12]. We previously showed [13] that N,N′-bis-(methoxycarbonyl)-1,4-benzoquinone diimine (V) is capable of reacting with some enamino ketones.…”