Base-Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring: Synthesis of Medium-Sized S,S-Heterocycles

被引：1

作者：

Dinc, Mert ^{[1
]}

Ismailoglu, Eda ^{[1
]}

Mert, Zeynep ^{[1
]}

Kaya, Kerem ^{[1
]}

Tayanc, Melda ^{[1
]}

Yucel, Baris ^{[1
]}

机构：

[1] Istanbul Tech Univ, Sci Fac, Dept Chem, TR-34469 Istanbul, Turkiye

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 22期

关键词：

INTRAMOLECULAR ADDITION; CLOSING METATHESIS; TERTIARY-AMINES; KETONES; DERIVATIVES; RADICALS; SULFIDES; BU/DMF; KOTBU; DMF;

D O I：

10.1021/acs.orglett.3c01118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Base-mediated rearrangementof 1,3-dithianyl-substitutedpropargylaminesin DMF via expansion of the dithiane ring has been reported. The rearrangementprovided 9-membered amino-functionalized sulfur-containing heterocycles(dithionine derivatives) in good yields under mild conditions. Propargylaminesbearing 5-membered 1,3-dithiolane and 7-membered 1,3-dithiepane ringsrearranged in a similar manner yielding 8- and 10-membered S,S-heterocycles, respectively.

引用

页码：4028 / 4032

页数：5

共 23 条

[21] CONSTRUCTION OF MEDIUM-SIZED AND LARGE-SIZED CYCLIC BETA-KETO-ESTERS (OR NITRILES) VIA ONE-POT 3-CARBON RING EXPANSION OF CARBOCYCLIC BETA-KETO-ESTERS AND ITS APPLICATION TO THE SYNTHESIS OF (-)-MUSCONE
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[22] Chiral lithium amide base-mediated rearrangement of bis-protected meso-4,5-dihydroxy cyclohexene oxides:: enantioselective synthesis of (4R,5S)- and (4S,5R)-4,5-bis(tert-butyldimethylsilyloxy)cyclohex-2-enone
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JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15): : 2435 - 2441
[23] SYNTHESIS, STRUCTURE AND REACTIONS OF SECO-STEROIDS CONTAINING A MEDIUM-SIZED RING .24. MOLECULAR-STRUCTURES OF THE INTERNAL ACETALS DERIVED FROM (1S,10S) DIHYDROXY-3-BETA-ACETOXY-5, 10-SECO-5-CHOLESTANONES AND (1R,10R)-DIHYDROXY-3-BETA-ACETOXY-5,10-SECO-5-CHOLESTANONES
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