Synthesis of 2-Cyano-3-Nitroporphyrin Derivatives with Silyl Cyanide

Abstract

2-Cyano-3-nitroporphyrin derivatives were synthesised by the reaction of 2-nitroporphyrin with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride with moderate yields. The reaction took place regioselectively on the 3-position carbon of the porphyrins, which was confirmed by X-ray analysis.

Synthesis, Structural and Redox Properties of Vanadyl β‐Cyanoporphyrin and its Utilization as Efficient Catalyst for Epoxidation of Olefins and Oxidative Bromination of Phenols

“…[14] Recently, mixed substituted 2-cyano-3-nitroporphyrin was synthesized from 2nitroporphyrin using tetrabutylammonium fluoride and trimethylsilyl cyanide as a cyanating agent in tetrahydrofuran at room temperature. [15] The current methodology employed in this work reduces the number of steps and improves overall yield for the synthesis of 1. Cyano-substituted porphyrins are quite useful in catalysis, molecular self-assemblies, and photoelectrochemical devices.…”

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2- 10,15, (1) having cyano group at one of β-pyrrolic positions using nucleophilic substitution reaction of tetrabutylammonium cyanide (TBACN) on free-base 2-nitro-5,10,15,20-tetraphenylporphyrin, and its oxidovanadium(IV) complex [V IV OTPPCN] (2) were synthesized in good yields. Both the porphyrins 1 and 2 have been characterized by UV-Vis spectroscopy, mass spectrometry, and cyclic voltammetric techniques.

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Synthesis of 2H-Chromene-4-Carbonitriles Via Trimethylsilyl Cyanide

“…with the advantages of being readily available, easy to handle and high activity. 10 In continuation of our work on the synthesis of nitrile derivatives [11][12][13] and chromenes derivatives, 14 here we report the synthesis of 2-aryl-2H-chromene-4-carbonitrile derivatives by the reaction of 2-aryl-3-nitro-2H-chromene with trimethylsilyl cyanide in the presence of TBAF via a Michael addition/ elimination pathway (Scheme 1).…”

Synthesis of 2-(1-Oxo-2,3-Dihydro-1H-Pyrrolizin-2-yl)-2-(Aryl)Acetonitrile Derivatives Via Michael Addition of Trimethylsilyl Cyanide

“…10 Trimethylsilyl cyanide (TMSCN) is a better cyanide source than others such as sodium cyanide (NaCN) and tetrabutylammonium cyanide (Bu 4 NCN), with the advantages of it being readily available, easy to handle and possessing high activity. 11 In continuation of our work on the synthesis of nitrile derivatives [12][13][14] and pyrrolizine derivatives, 15,16 in this paper we report the synthesis of 2-aryl-2-(1-oxo-2,3-dihydro-1Hpyrrolizin-2-yl)acetonitrile derivatives by the reaction of (E)-2arylidene-2,3-dihydro-1H-pyrrolizin-1-ones with TMSCN in the presence of tetrabutylammonium fluoride (TBAF) via a Michael addition pathway (Scheme 1).…”