“…The preparative scope of the cyclization reaction was extended to the synthesis of a great variety of 2-alkylidene-3iminoindoles. [15][16][17] A number of substituents could be introduced both at the exocyclic double bond and at the indole moiety by variation of the substituents of the nitrile and of 8, respectively.…”
Section: Nitrile Dianionsmentioning
confidence: 99%
“…The high E -diastereoselectivity is a result of the steric interaction between the bulky arylimino and the phenyl group. The preparative scope of the cyclization reaction was extended to the synthesis of a great variety of 2-alkylidene-3-iminoindoles. − A number of substituents could be introduced both at the exocyclic double bond and at the indole moiety by variation of the substituents of the nitrile and of 8 , respectively. 7 Cyclization of Dilithiated Phenylacetonitrile with Oxalic Acid-Bis(imidoyl) dichlorides (Mechanism A)…”
“…The preparative scope of the cyclization reaction was extended to the synthesis of a great variety of 2-alkylidene-3iminoindoles. [15][16][17] A number of substituents could be introduced both at the exocyclic double bond and at the indole moiety by variation of the substituents of the nitrile and of 8, respectively.…”
Section: Nitrile Dianionsmentioning
confidence: 99%
“…The high E -diastereoselectivity is a result of the steric interaction between the bulky arylimino and the phenyl group. The preparative scope of the cyclization reaction was extended to the synthesis of a great variety of 2-alkylidene-3-iminoindoles. − A number of substituents could be introduced both at the exocyclic double bond and at the indole moiety by variation of the substituents of the nitrile and of 8 , respectively. 7 Cyclization of Dilithiated Phenylacetonitrile with Oxalic Acid-Bis(imidoyl) dichlorides (Mechanism A)…”
“…Synthesis of N,NЈ-bis(1-naphthyl)oxaldiimidoyl dichloride earlier for related 2-alkylidene-3-iminoindoles. [11] The formation of 4a can be explained, in analogy to our recently published method for the synthesis of 2-alkylidene-3-iminoindoles, [11] [3,2-b]quinoline 5a from 2 was accomplished in 59% overall yield (method A). We have also developed an alternative approach (Scheme 5): reflux of a THF solution of 3a and 2 in the presence of sodium hydride directly afforded 5a by a domino cylization/electrocyclization/elimination reaction (method B).…”
Section: Retrosynthetic Analysismentioning
confidence: 99%
“…We have recently reported [5] a new and efficient approach to 6H-indolino [3,2-b]quinolines by electrocyclization reactions of 2-alkylidene-3-iminoindoles, which are readily available from the reaction of nitriles with oxaldiimidoyl dichlorides. [11,12] Herein we wish to report the direct and efficient synthesis of 15H-benzo[h]benzo [6,7]indolo [3,2b]quinolines by domino cyclization/electrocyclization/elimination reactions of arylacetonitriles with N,NЈ-bis(1-naphthyl)oxaldiimidoyl dichlorides (Scheme 1). [13] The products, hexacyclic δ-carboline derivatives, are of pharmacological relevance and are new fluorescent markers.…”
The sodium hydride mediated cyclization of arylacetonitriles with oxalic acid bis(imidoyl) dichlorides, aza-analogues of oxalyl chloride, afforded functionalized 2-alkylidene-3-iminoindoles with very good regio- and E/Z selectivity. Excellent chemoselectivities were observed for functionalized substrates. Based on these results a domino "cyclization-lactamization" reaction of bis(imidoyl) chlorides with methyl 2-(cyanomethyl)benzoate was developed. This process allowed a convenient one-pot synthesis of indolo[1,2-b]isoquinolin-5-ones related to tryptanthrin. A new and convenient synthesis of delta-carbolines by intramolecular electrocyclization-elimination reactions of 2-alkylidene-3-iminoindoles was developed. It was shown that delta-carbolines selectively bind to triplex or duplex DNA (intercalation). Indirubine analogues were prepared by deprotection and lactonization of functionalized 2-alkylidene-3-iminoindoles.
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