The [1 + 4] cycloaddition of isocyanides with 1-aryl-2-nitro-1-propenes. Methyl 2-nitro-3-arylpropenoates and methyl 2-nitro-2,4-pentadienoates. Synthesis of 1-hydroxyindoles and 1-hydroxypyrroles

Foucaud, A.; Razorilalana-Rabearivony, Claudia; Loukakou, Emile; Person, H.

doi:10.1021/jo00169a004

Cited by 36 publications

(10 citation statements)

References 7 publications

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“…The synthesis of 1-hydroxyindoles 21 was achieved by a [1 + 4] cycloaddition reaction of isocyanides with aryl nitroalkenes 19 (Scheme 9). 16 However, in this case the nitrogen of the indole nucleus arose from the nitro group and not from the isocyano group.…”

Section: Methodsmentioning

confidence: 86%

Synthesis of indole derivatives via isocyanides

et al. 2006

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Section: Methodsmentioning

confidence: 86%

Synthesis of indole derivatives via isocyanides

et al. 2006

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“…In another example, in an attempt to synthesize highly functionalized 1-hydroxypyrrole or 1-hydroxyindole derivatives 159, Foucaud and co-workers explored a formal [4+1] annulation of isocyanide 1 with a,b-unsaturated aryl nitro derivatives 158. 65 The reaction afforded moderate to good yields of the desired products under benzene/acetonitrile reflux conditions. Under the set of conditions, a,b-unsaturated aryl nitro derivatives displayed a cycloaddition reaction smoothly with isocyanides and the product got converted into 1-hydroxypyrrole or 1-hydroxyindole analogues.…”

Section: Nitro-olefinsmentioning

confidence: 97%

Isocyanide based [4+1] cycloaddition reactions: an indispensable tool in multi-component reactions (MCRs)

et al. 2016

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The advent of cycloaddition reactions in the synthesis of heterocycles and their ever burgeoning applications in the fields of material chemistry, catalysis and drugs have been a profound scientific development. In particular, isocyanide based cycloaddition reactions have been harbingers of an exciting new chapter in the realms of organic synthesis. The emergence of numerous synthetic protocols utilizing formal cycloaddition of isocyanides with conjugated heterodienes has unleashed countless opportunities to design and synthesize diverse heterocyclic scaffolds. To date, there has not been any exclusive review on a formal [4+1] cycloaddition involving isocyanides. The present review highlights the journey of formal [4+1] cycloaddition reactions of isocyanides with diverse electrophilic substrates viz. oxadienes, azadienes, thioacyl imines, alkylidene amides, alkylidene hydrazines, α,β-unsaturated nitro compounds, α-thioxothioamides, nitroso alkenes, acyl imines, vinyl ketenes, vinyl isocyanates, etc. to afford functionalized pyrroles, imidazoles, furans, oxazoles, pyrazoles, etc.

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“…2 zusammengestellt*). (1) 478 (14) 496 (13) 394 (11) 415 (13) 386 (12) 417 (11) 485 (15) 716 (17) 411 (14) 533 (11) 658 (12) 734 (27) 356 (12) 483 (10) 440 (9) 554 (19) 373 (13) 384 (11) 381 (11) 477 (17) 455 (18) 533 (17) 648 (20) 5 16( 17) 419 (15) 425 (16) 520 (15) 472 (13) 42605) 435 (14) 51703) 626 (19) 719 (18) 492 (17) 657 (13) 466(1 I) 587 (22) 396 (14) 777 (14) 601 (11) (17) 362 (14) 549 (15) 354 (12) 345 (14) 311 (13) 373 (12) 371 (15) 668 (17) 423 (15) 621 (12) 554 (12) 74809) 345 (15) 476 (11) 382 (11) 727 (25) 298 (13) 322 (12) 35...…”

Section: Reaktion Von Triazin 3 Rnit Den Formaldehydhydrazonen 2a-dunclassified

“…-22 (14) lOI (14) 95 (13) -42(11) -114 (10) -1(24) 67(22) Il (13) 37 (12) -50 (11) 33 (9) -118(10) -43 (9) -178(11) 29(9) -11 (9) 103 (8) 29(22) 298 (18) -38(12) 2 0 1 ) -65 (11) 43(9) -84 (12) 87(10) -199 (21) 112 (15) 63(22) 81 (17) -78 (20) 257 (16) -118 (19) 207(16) 121 (17) 97(15) 28 (14) 60 ( …”

Section: (15)unclassified

Zur Reaktivität elektronenreicher CN‐Mehrfachbindungen gegenüber akzeptorsubstituierten 1,2,4‐Triazinen

Seitz

Dietrich

Dhar

et al. 1986

Archiv der Pharmazie

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319f86Reaktivitat elektronenreicher CN-Mehrfachbindungen 799 Formaldehydhydrazone addieren sich auf zwei verschiedenen Reaktionswegen an das Azadiensystem des Triazins 3. Einerseits entstehen selektiv die Pyrimidine 4 via Diels-Alder-Reaktion mit inversem Elektronenbedarf, andererseits erfolgt nucleophile Addition an C-5 des Triazins 3 zu 7. Die Konstitution von 7d wird durch Rontgenstrukturanalyse bewiesen. Die Umsetzung der Triazine 3 und 17 mit Isonitrilen fuhrt iiber eine [4+ 11-Cycloaddition rnit nachfolgender [4+2]-Cycloreversion zu den Pyrrolderivaten 15, 16 und 19.

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The [1 + 4] cycloaddition of isocyanides with 1-aryl-2-nitro-1-propenes. Methyl 2-nitro-3-arylpropenoates and methyl 2-nitro-2,4-pentadienoates. Synthesis of 1-hydroxyindoles and 1-hydroxypyrroles

Abstract: Cj; mass spectrum, m/e (relative intensity) 126 (M+, 17), 96 (45), 68 (100); caled for C7H10O2 m/e 126.0681, found m/e 126.0687. traas-17: yield 65% (from threo-7c), 49% (from 11c); bp 103 °C (12 mmHg); IR (neat film) 3000 (m), 1780 (s), 1645 (w), 1010 (s), 920 cm"1 (s);

Cited by 36 publications

References 7 publications

Synthesis of indole derivatives via isocyanides

Synthesis of indole derivatives via isocyanides

Isocyanide based [4+1] cycloaddition reactions: an indispensable tool in multi-component reactions (MCRs)

Zur Reaktivität elektronenreicher CN‐Mehrfachbindungen gegenüber akzeptorsubstituierten 1,2,4‐Triazinen

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