Synthesis of nitrogen heterocycles via Pd-catalyzed cross-coupling of o-alkenyl anilides with vinylic halides and triflates

Larock, Richard C.; Pace, Paola; Yang, Hoseok; Russell, Charles E.; Cacchi, Sandro; Fabrizi, Giancarlo

doi:10.1016/s0040-4020(98)00589-4

Cited by 37 publications

(17 citation statements)

References 35 publications

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“…Similar results concerning the synthesis of nitrogen heterocycles by the Pd‐catalyzed cross‐coupling of 2‐alkenylanilines with vinylic triflates and halides have been reported recently 23…”

Section: Resultssupporting

confidence: 84%

New Metal‐Catalyzed Synthesis of Quinoline and Chromene Skeletons

Deagostino¹,

Farina²,

Prandi³

et al. 2006

Eur J Org Chem

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Alkoxy‐functionalized butadienylboronic esters have been synthesized starting from α,β‐unsaturated acetals and cross‐coupled with both N‐protected and N‐unprotected 2‐bromo‐ and 2‐iodoaniline, and with 2‐iodophenol. In particular, N‐tosyl‐protected dienylanilines can be transformed under mild conditions into quinolines and quinolinones, in the presence of a PdII catalyst. Moreover, the cross‐coupling reaction between butadienylboronic esters and iodophenol directly affords chromenes that can be successively transformed into chromenones. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Section: Resultssupporting

confidence: 84%

New Metal‐Catalyzed Synthesis of Quinoline and Chromene Skeletons

Deagostino¹,

Farina²,

Prandi³

et al. 2006

Eur J Org Chem

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“…Data for iodide 21: mp 102-104 °C; 1 H NMR (300 MHz, CDCl 3 ) δ 7.46 (d, J = 7.9 Hz, 1 H), 7.31-7.18 (m,7 H), 7.13 (m, 1 H), 6.42 (s, 1 H), 4.82 (m, 1 H), 4.32 (s, 2H), 4.28 (d, J = 6.0 Hz, 2 H); 13 In a two neck round bottom flask, Mg (0.036 g, 0.00149 mol, 3 equiv) in THF (2 mL) was treated with 2-bromopropene (0.18 g, 0.00149 mol, 3 equiv), added dropwise via syringe. 7 The mixture was stirred at 23 • C for 1 h, then iodide 21 (0.2 g, 0.00049, 1 equiv) in THF (2 mL) was added and the mixture was stirred an additional hour. The reaction was quenched with saturated aqueous NH 4 Cl and extracted with CH 2 Cl 2 .…”

Section: N-benzyl-n'-(2-methyl-allyl-phenyl)-sulfamide (7)mentioning

confidence: 99%

Copper(II) Acetate Promoted Intramolecular Diamination of Unactivated Olefins.

2005

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Representative Sulfamide Synthesis: N-(2-Allyl-phenyl)-N'-benzyl-sulfamide (1a). 2A solution of o-Allylaniline (3.00 g, 22.5 mmol) and triethylamine (4.56 g, 5.98 mL, 45.08 mmol) in dry benzene (100 mL) was cooled to 0 O C and treated with a 0.1 M solution of benzylsulfonylchloride 1 in benzene (7.73 g, 37.6 mmol). After warming to room temperature, the mixture was allowed to stir for 24 h and the solvent was removed in vacuo. Chromatograpy of the crude oil on SiO 2 (10-30% Et 2 O/hexanes gradient) provided 6.14 g, 90% of sulfamide 1a as a yellow/brown solid.

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“…It is well-documented that substituted o-allylanilines are useful precursors for the synthesis of diverse classes of nitrogen-containing heterocycles, for example they are known to lead to indolines, [1][2][3][4][5][6][7][8] indoles, [6][7][8][9][10] pyrrolo [1,2a]indolones, 11,12 indolo [1,2-b]isoquinolinones and benzo [5,6] [1,2]thiazino[2,3-a]indole 5,5-dioxides, [13][14][15][16] imidazo [1,5-a]indolones and [1,2,5]thiadiazolo[2,3-a]indole 1,1-dioxides, 17,18 quinolines, 19 dihydroquinolines, [20][21][22][23] tetrahydroquinolin-2-ones, [24][25][26] 4,5-dihydro-3H-1-benzazepines, 19 2,5-dihydro-1H-1-benzazepines, 27 tetrahydro-1benzazepines, [25][26][27][28][29] tetrahydro-1-benzazocines, 30 3,4,5,6tetrahydro-1-ben...…”

mentioning

confidence: 99%

Stereoselective Synthesis of Novel 2-Alkenyl-2,3,4,5-tetrahydro-1,4-epoxy-1-benzazepines and 2-Alkenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ols

et al. 2012

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New series of polyfunctionalized 2,3,4,5-tetrahydro-1,4-epoxy-1-benzazepines and 2,3,4,5-tetrahydro-1H-1-benzazepin-4-ols substituted at C2 with 2-methylprop-1-enyl, (E)-styryl, and (E)-pent-1-enyl were synthesized starting from the corresponding N-alkenyl-substituted [prenyl, trans-cinnamyl, (E)-hex-2-enyl] 2-allylanilines by a three-step sequence consisting of selective oxidation of aromatic secondary amines, intramolecular nitrone-olefin 1,3-dipolar cycloaddition, and reductive cleavage. The intramolecular 1,3-dipolar cycloaddition is stereoselective favoring the exo-cycloadducts (ratio exo/endo 2-3:1). The stereochemistry was determined by exhaustive NMR analysis and X-ray diffraction.

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Synthesis of nitrogen heterocycles via Pd-catalyzed cross-coupling of o-alkenyl anilides with vinylic halides and triflates

Cited by 37 publications

References 35 publications

New Metal‐Catalyzed Synthesis of Quinoline and Chromene Skeletons

New Metal‐Catalyzed Synthesis of Quinoline and Chromene Skeletons

Copper(II) Acetate Promoted Intramolecular Diamination of Unactivated Olefins.

Stereoselective Synthesis of Novel 2-Alkenyl-2,3,4,5-tetrahydro-1,4-epoxy-1-benzazepines and 2-Alkenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ols

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