Thallium(III) p-Tosylate Mediated Oxidative 2,3-Aryl Rearrangement: A New Useful Route to Ipriflavone and Its Analogs

被引：10

作者：

Muthukrishnan, M. ^{[1
]}

Singh, Om V. ^{[1
]}

机构：

[1] Trop Bot Garden & Res Inst, Phytochem Div, Trivandrum, Kerala, India

来源：

SYNTHETIC COMMUNICATIONS | 2008年 / 38卷 / 22期

关键词：

Flavanones; ipriflavone; isoflavones; oxidative rearrangement; thallium(III) p-tosylate;

D O I：

10.1080/00397910802238734

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new route for the synthesis of ipriflavone, an antiosteoporotic agent, is described that has four steps and 60% yields starting from resacetophenone (2). The key step of the present methodology is thallium(III) p-tosylate mediated oxidative 2,3-aryl rearrangement of flavanone to generate the isoflavone ring system of ipriflavone in a highly efficient manner.

引用

页码：3875 / 3883

页数：9

共 9 条

[1] Thallium(III) p-tosylate (TTS) mediated oxidative rearrangement of 2-naphthyl and 2-heteroarylchromanones
Kurapati, Chidvilas
Muthukrishnan, M.
Singh, Om, V
Gundla, Rambabu
INDIAN JOURNAL OF CHEMISTRY, 2022, 61 (09): : 923 - 927
[2] Novel synthesis of rotenoid, pongarotene, by oxidative rearrangement using thallium(III) p-tosylate
Kurapati, Chidvilas
Singh, Om, V
Gundla, Rambabu
SYNTHETIC COMMUNICATIONS, 2022, 52 (08) : 1190 - 1197
[3] THALLIUM(III) P-TOSYLATE MEDIATED OXIDATIVE REARRANGEMENT IN SUBSTITUTED CHROMANONES - A NOVEL-APPROACH TO THE SYNTHESIS OF SUBSTITUTED CHROMONES AND TETRAHYDROXANTHONES
SINGH, OV
GEORGE, V
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1995, 34 (10): : 856 - 864
[4] Synthesis of isoflavones containing naturally occurring substitution pattern by oxidative rearrangement of respective flavanones using thallium(III) p-tosylate
Singh, OV
Muthukrishnan, M
Sunderavadivelu, M
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2005, 44 (12): : 2575 - 2581
[5] Thallium(III) p-tosylate-mediated oxidative [1,2] rearrangement of 2-naphthyl and 2-heteroarylchromanones
Kurapati, Chidvilas
Muthukrishnan, Murugan
Singh, Om, V
Gundla, Rambabu
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2022, 59 (01) : 172 - 177
[6] OXIDATIVE 1,2-ARYL REARRANGEMENT IN FLAVANONES USING THALLIUM(III) PARA-TOLYL SULFONATE (TTS) - A NEW USEFUL ROUTE TO ISOFLAVONES
SINGH, OV
GARG, CP
KAPOOR, RP
TETRAHEDRON LETTERS, 1990, 31 (19) : 2747 - 2750
[7] Facile synthesis of 2-aryl or β,γ-unsaturated esters via 1,2-Migration from aryl or α,β-unsaturated ketones using thallium(III) p-tosylate
Lee J.I.
Journal of the Korean Chemical Society, 2017, 61 (03): : 125 - 128
[8] OXIDATIVE REARRANGEMENT OF 2'-ACETAMIDOCHALCONES WITH THALLIUM(III) NITRATE - A NEW ROUTE TO 3-ARYL-4(1H)-QUINOLONES
TOKES, AL
ANTUS, S
LIEBIGS ANNALEN DER CHEMIE, 1993, (08): : 927 - 929
[9] A NEW ROUTE TO 2-ARYL-4-QUINOLONES VIA THALLIUM(III) P-TOLYSULPHONATE MEDIATED OXIDATION OF 2-ARYL-1,2,3,4-TETRAHYDRO-4-QUINOLONES
SINGH, OV
KAPIL, RS
SYNTHETIC COMMUNICATIONS, 1993, 23 (03) : 277 - 283

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