Facile Method for Conversion of 2-(Chloroseleno)benzoyl Chloride into 2-Substituted 3-Hydroxybenzo[b]selenophenes

Abstract

The easily accessible 2-(chloroseleno)benzoyl chloride has broad application in the synthesis of benzizoselenazol-3(2H)-ones and benzo[b]selenophen-3(2H)-ones. Treatment of 2-acylbenzo[b]selenophen-3(2H)-ones with nitrogen nucleophiles such as hydrazines and hydroxylamine resulted in formation of 2-substituted 3-hydroxybenzo[b]selenophenes in 72–98% yield.

Keywords:

• Benzo[b]selenophenes
• 2-(chloroseleno)benzoyl chloride
• hydrazines
• selenaheterocycles

ACKNOWLEDGMENT

The work was supported by the Ministry of Science and Higher Education (Grant 351788/20305).

Notes

^a Some benzo[b]selenophen-3(2H)-ones 1 have been reported earlier: 1a,^{[ 13 ]} 1d,^{[ 14 ]} and 1h.^{[ 13 ]}

^a Some benzo[b]selenophenes 7 have been reported earlier: 7b ^{[ 13 ]} (yield 59%), 7c ^{[ 13 ]} (yield 28%), and 7d ^{[ 13 , 14 ]} (yield 58%).

^b Yields of 7 with MeNHNH₂ as reagent.

^c Yields of 7 with PhNHNH₂ as reagent.

^d Yields of 7 with NH₂OH as reagent.