Construction of 2-Arylbenzo[4,5]thieno[2,3-d]thiazole Skeleton via CuCl/S-Mediated Three-Component Reaction

Abstract

An exclusive thiophene-fused polycyclic π-conjugated 2-arylbenzo­[4,5]­thieno­[2,3-d]­thiazole skeleton was constructed via a one-pot CuCl-mediated three-component reaction, using 2-(2-bromophenyl)­acetonitrile and aromatic aldehydes as substrates and elemental sulfur as sulfur source in the presence of K2CO3 and 1,10-phen in DMSO. A plausible reaction mechanism was proposed, which involved formation of benzo­[b]­thiophen-2-amines through cyclization of 2-bromophenyl acetonitrile and sulfur, and subsequent intramolecular condensation/dehydrogenation with aromatic aldehydes.

Recent Advances in the Synthesis of Heterocycles via Reactions Involving Elemental Sulfur

“…According to the proposed reaction pathway, it is possible that 2-aminobenzothiophene 125 displays similar behavior (Scheme 46). [52] Generated in situ from o-bromophenylacetonitriles 122 by copper-catalyzed sulfuration with elemental sulfur, this heteroaromatic amine could be further sulfuration and trapped with a benzadehyde to provide 2-phenylbenzo [4,5] thieno[2,3-d]thiazole 124.…”

Recent Advances in Multicomponent Reactions with Organic and Inorganic Sulfur Compounds

“… [34] Fused thieno[3,2‐d]thiazoles ( 15 ) may be applied to thiophene‐containing high‐performance optoelectronic materials. A copper‐catalyzed three‐component reaction using 2‐(2‐bromophenyl)acetonitrile ( 16 ) and aromatic aldehydes ( 17 ) and elemental sulfur as substrates was reported by Du and co‐workers, [35] leading to a 2‐arylbenzo[4,5]thieno[2,3‐d]thiazole skeleton ( 18 ) in good yields. This is the first example of using a copper‐catalyzed three‐component process through one‐pot synthesis of the exclusive 2‐arylbenzo[4,5]thieno[2,3‐d]thiazoles (Scheme 4).…”

Synthesis of densely substituted pyridine derivatives from nitriles by a non-classical [4+2] cycloaddition/1,5-hydrogen shift strategy

“…2B, in the nucleophilic addition of nitriles, the most reported reaction partners have been focused on the highly reactive nitrogen, [44][45][46][47][48][49][50][51][52] oxygen, [53][54][55][56][57][58][59][60][61] and sulfur nucleophiles till now. [62][63][64] For carbon pronucleophiles, the related studies are only limited to sp, sp 2 , and sp 3 with α-electron withdrawing group (i.e. cyano, carbonyl, ester groups) carbons, though some elegant work has been made by using transition metal catalysts.…”