ChemInform Abstract: Copper‐Catalyzed Three‐Component One‐Pot Synthesis of Substituted 2‐Aryl‐1,3‐benzoselenazoles.

Abstract

Copper-Catalyzed Three-Component One-Pot Synthesis of Substituted 2-Aryl--1,3-benzoselenazoles. -A simple method for the synthesis of the title compounds (III) using inexpensive and readily available 2-iodoanilines (I), various aromatic aldehydes (II) and selenium powder without ligands and other additives under mild reaction conditions is presented. -(SU, T.; XIE, S.; LI, B.; YAN, J.; HUANG*, L.; LI, X.; Synlett 26 (2015) 2, 215-220, http://dx.

Elemental Selenium in the Synthesis of Selenaheterocycles

“…The reactions proceeded in moderate-togood yields with good functional tolerance [134]. Another approach to preparation of 2-substituted 1,3-benzoselenazole derivatives 161 consisted in (1) the three-component one-pot reactions of readily available 2-iodoanilines 162, arylacetic acids 160 or arylmethyl chlorides 163, as well as selenium powder in the presence of CuBr in DMSO at 120 °C [135], or (2) in the three-component reactions of 2-iodoanilines 162, aromatic and heteroaromatic aldehydes 164, as well as elemental Se in DMSO at 120 °C in the presence of a Cu powder catalyst [136]. Substituted 1,3-benzoselenazoles 161 were prepared by these methods in moderate-to-high yields (Scheme 63).…”

“…Annulation in the case of 2-unsubstituted indoles proceeds at the indole substituent, and in the case of 2-arylsubstituted indoles, at the aryl substituent of intermediate 3-vinylindole. Another approach to preparation of 2-substituted 1,3-benzoselenazole derivatives 161 consisted in (1) the three-component one-pot reactions of readily available 2-iodoanilines 162, arylacetic acids 160 or arylmethyl chlorides 163, as well as selenium powder in the presence of CuBr in DMSO at 120 Another approach to preparation of 2-substituted 1,3-benzoselenazole derivatives 161 consisted in (1) the three-component one-pot reactions of readily available 2-iodoanilines 162, arylacetic acids 160 or arylmethyl chlorides 163, as well as selenium powder in the presence of CuBr in DMSO at 120 °C [135], or (2) in the three-component reactions of 2-iodoanilines 162, aromatic and heteroaromatic aldehydes 164, as well as elemental Se in DMSO at 120 °C in the presence of a Cu powder catalyst [136]. Substituted 1,3-benzoselenazoles 161 were prepared by these methods in moderate-to-high yields (Scheme 63).…”

“…• C[135], or(2) in the three-component reactions of 2-iodoanilines 162, aromatic and heteroaromatic aldehydes 164, as well as elemental Se in DMSO at 120 • C in the presence of a Cu powder catalyst[136]. Substituted 1,3-benzoselenazoles 161 were prepared by these methods in moderate-to-high yields (Scheme 63).…”