Interaction of 4-oxoalkane-1,1,2,2-tetracarbonitriles with Lawesson's reagent – a new approach to the synthesis of 2,2′-disulfanediylbis(1H-pyrroles). The synthesis of photochromic diarylethene with a disulfide bridge

Abstract

Transformation of 4-oxoalkane-1,1,2,2-tetracarbonitriles under the action of Lawesson's reagent leads to 2,2′-disulfanediylbis(1H-pyrrole-3-carbonitriles) in good yields.

Metal-Involving Synthesis and Reactions of Oximes

“…This reaction represents an unconventional example of (NC) 2 CC­(CN) 2 reactivity. In metal-free chemistry, tetracyanoethene is known to be involved in [4 + 2]-, − [3 + 2]-, , [2 + 2]-, − and [2 + 1]-cycloadditions, and only a few examples of the nucleophilic addition of C -nucleophiles − have been reported. The mechanism discussed for this reaction, depicted in Scheme , includes the initial reversible exchange of the CO ligand to the alkene (b) followed by the insertion of the alkene into the Re–O bond (c) to give the coupling product.…”

Recent Advances for the Synthesis of N‐Unsubstituted Pyrroles

“…Belikov M.Y. and collegues [56] developed a new method to synthesize 2,2′‐disulfanediylbis(1 H‐ pyrrole‐3‐carbonitriles) 174 from 4‐oxoalkane‐1,1,2,2‐tetracarbonitriles 172 using Lawesson's reagent 173 (Scheme 57).…”

Diversity of Lawesson's Reagent: Advances and Scope

“…An innovative approach for the decoration of disulfide linkage containing pyrrole 27 via the nucleophilic attack of readily available 4‐oxo‐tetracarbonitriles 26 to 1 was established by Belikov and coworkers . They proposed initially the attachment of active site of 26 with monomer 2 provided the formation of intermediate 28 .…”

“…An innovative approach for the decoration of disulfide linkage containing pyrrole 27 via the nucleophilic attack of readily available 4-oxo-tetracarbonitriles 26 to 1 was established by Belikov and coworkers. [11] They proposed initially the attach- 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 During their study the authors envisioned that they can utilize the presence of this disulfide linkage bearing framework for the design and synthesis of photochromic architechture. Henceforth, keeping in mind that diarylethenes with thienyl substituents are the most encouraging candidates because of their photochromic nature and for practical purposes in diferent fields, they delineated compound 31 from 30 using the same methodology (Scheme 10).…”