Oxidative Cleavage of 1,3-Disubstituted Benzo[c]furans with Activated Manganese­ Dioxide: A Facile Preparation of 1,2-Di(het)aroylbenzenes

Ramakrishnan Sivasakthikumaran; Meganathan Nandakumar; Arasambattu K. Mohanakrishnan

doi:10.1055/s-0034-1378352

Synlett, Table of Contents

Synlett 2014; 25(13): 1896-1900
DOI: 10.1055/s-0034-1378352

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Oxidative Cleavage of 1,3-Disubstituted Benzo[c]furans with Activated Manganese Dioxide: A Facile Preparation of 1,2-Di(het)aroylbenzenes

Ramakrishnan Sivasakthikumaran

Department of Organic Chemistry, School of Chemical Sciences, University of Madras, Guindy Campus, Chennai 600 025, Tamil Nadu, India Fax: +91(44)22352494 Email: mohanakrishnan@unom.ac.in Email: mohan_67@hotmail.com

,

Meganathan Nandakumar

Department of Organic Chemistry, School of Chemical Sciences, University of Madras, Guindy Campus, Chennai 600 025, Tamil Nadu, India Fax: +91(44)22352494 Email: mohanakrishnan@unom.ac.in Email: mohan_67@hotmail.com

,

Arasambattu K. Mohanakrishnan*

Department of Organic Chemistry, School of Chemical Sciences, University of Madras, Guindy Campus, Chennai 600 025, Tamil Nadu, India Fax: +91(44)22352494 Email: mohanakrishnan@unom.ac.in Email: mohan_67@hotmail.com

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Abstract

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Abstract

Manganese dioxide mediated oxidative cleavage of 1,3-disubstituted benzo[c]furans in dichloromethane at room temperature gave good yields of 1,2-di(het)aroylbenzenes.

Key words

heterocycles - polycycles - diketones - ring opening - oxidation - manganese dioxide

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References

References and Notes

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14 1,2-Phenylenebis(2-thienylmethanone) (2a); Typical Procedure MnO₂ (0.57 g, 7.09 mmol) was added to a stirred solution of benzo[c]furan 1a (0.5 g, 1.77 mmol) in CH₂Cl₂ (20 mL), and the mixture was stirred at r.t until the benzo[c]furan was consumed (~4 h). The mixture was then filtered through Celite and the residue was washed with CH₂Cl₂ (2 × 10 mL). The combined filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (silica gel; 5% EtOAc–hexane) to give a brown solid; yield: 0.48 g (92%); mp 150–152 °C (Lit. see ref. 1b 149–150 °C); IR (KBr): 1623, 1582, 1568, 1514, 1416 cm^–1; ¹H NMR (300 MHz, CDCl₃): δ = 7.66–7.64 (m, 2 H, ArH), 7.58–7.56 (m, 4 H, ArH), 7.39–7.38 (m, 2 H, ArH), 6.99–6.96 (m, 2 H, ArH); ¹³C NMR (75 MHz, CDCl₃): δ = 188.3, 144.0, 139.4, 135.1, 135.0, 130.6, 129.2, 128.1; DEPT-135 (75 MHz, CDCl₃): δ = 135.2, 135.0, 130.6, 129.2, 128.1; HRMS (EI): m/z [M⁺] calcd for C₁₆H₁₀O₂S₂: 298.0122; found: 298.0121.

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Oxidative Cleavage of 1,3-Disubstituted Benzo[c]furans with Activated Manganese­ Dioxide: A Facile Preparation of 1,2-Di(het)aroylbenzenes

Oxidative Cleavage of 1,3-Disubstituted Benzo[c]furans with Activated Manganese Dioxide: A Facile Preparation of 1,2-Di(het)aroylbenzenes