Synthetic and Mechanistic Investigation of an Unexpected Intramolecular 1-5 Nitrogen to Carbon Tosyl Migration

被引：1

作者：

Mathenjwa, Gciniwe S. ^{[1
]}

Akerman, Matthew P. ^{[1
]}

Bode, Moira L. ^{[2
]}

Veale, Clinton G. L. ^{[3
]}

机构：

[1] Univ KwaZulu Natal, Sch Chem & Phys, Private Bag X01, ZA-3209 Scottsville, South Africa

[2] Univ Witwatersrand, Sch Chem, Mol Sci Inst, Private Bag 3,PO WITS, ZA-2050 Johannesburg, South Africa

[3] Univ Cape Town, Dept Chem, ZA-7700 Cape Town, South Africa

来源：

SYNLETT | 2022年 / 33卷 / 19期

基金：

新加坡国家研究基金会;

关键词：

sulfonyl migration; tosyl hydrazone; tetrahydroindazolone; pyrazolidinones; HSP90; inhibitors; HSP90; INHIBITORS; CYCLOADDITIONS; DERIVATIVES;

D O I：

10.1055/a-1893-7550

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Controlled sulfonyl migration is considered an important transformation for total synthesis and scaffold elaboration. Accordingly, efforts to understand the underlying properties of these often serendipitously identified reactions have important implications. Following the attempted synthesis of a tetrahydroindazolone analogue, we report here an unexpected 1,5-nitrogen to carbon tosyl migration, resulting in the isolation of an unusual sulfonated dimedone. Synthetic and mechanistic investigations provide early insight into the scope of this reaction, with two potential mechanisms proposed.

引用

页码：1907 / 1912

页数：6

共 29 条

[1] An unprecedented N- to C-sulfonyl migration in the reaction of azomethine amine and allenoates: access to arylsulfonylmethyl substituted pyrazolo[1,5-c]quinazoline and mechanistic studies [J].

Ansari, Arshad J. ;

Wani, Aabid Abdullah ;

Maurya, Antim K. ;

Verma, Sarika ;

Agnihotri, Vijai K. ;

Sharon, Ashoke ;

Bharatam, Prasad, V ;

Sawant, Devesh M. .

CHEMICAL COMMUNICATIONS, 2019, 55 (98) :14825-14828

[2] Optical and Radioiodinated Tethered Hsp90 Inhibitors Reveal Selective Internalization of Ectopic Hsp90 in Malignant Breast Tumor Cells [J].

Barrott, Jared J. ;

Hughes, Philip F. ;

Osada, Takuya ;

Yang, Xiao-Yi ;

Hartman, Zachary C. ;

Loiselle, David R. ;

Spector, Neil L. ;

Neckers, Len ;

Rajaram, Narasimhan ;

Hu, Fangyao ;

Ramanujam, Nimmi ;

Vaidyanathan, Ganesan ;

Zalutsky, Michael R. ;

Lyerly, H. Kim ;

Haystead, Timothy A. .

CHEMISTRY & BIOLOGY, 2013, 20 (09) :1187-1197

[3] A NOVEL LYSINE-PROTECTING PROCEDURE FOR CONTINUOUS-FLOW SOLID-PHASE SYNTHESIS OF BRANCHED PEPTIDES [J].

BYCROFT, BW ;

CHAN, WC ;

CHHABRA, SR ;

HONE, ND .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (09) :778-779

[4] Synthesis and structural study of tetrahydroindazolones [J].

Claramunt, Rosa A. ;

Lopez, Concepcion ;

Perez-Medina, Carlos ;

Pinilla, Elena ;

Torres, A. Rosario ;

Elguero, Jose .

TETRAHEDRON, 2006, 62 (50) :11704-11713

[5] A Fluorescent Hsp90 Probe Demonstrates the Unique Association between Extracellular Hsp90 and Malignancy in Vivo [J].

Crowe, Lauren B. ;

Hughes, Philip F. ;

Alcorta, David A. ;

Osada, Takuya ;

Smith, Aaron P. ;

Totzke, Juliane ;

Loiselle, David R. ;

Lutz, Isaac D. ;

Gargesha, Madhusudhana ;

Roy, Debasish ;

Roques, Jose ;

Darr, David ;

Lyerly, H. Kim ;

Spector, Neil L. ;

Haystead, Timothy A. J. .

ACS CHEMICAL BIOLOGY, 2017, 12 (04) :1047-1055

[6] Process Development and Scale-Up of an Hsp90 Inhibitor [J].

Duan, Shengquan ;

Venkatraman, Sripathy ;

Hong, Xuechuan ;

Huang, Kenneth ;

Ulysse, Luckner ;

Mobele, Bingidimi I. ;

Smith, Alexander ;

Lawless, Lawrence ;

Locke, Andrew ;

Garigipati, Ravi .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (11) :1787-1793

[7] Synthetic and mechanistic aspects of sulfonyl migrations [J].

Flynn, Aaran J. ;

Ford, Alan ;

Maguire, Anita R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (14) :2549-2610

[8] Regioselective Thermal [3+2]-Dipolar Cycloadditions of α-Diazoacetates with α-Sulfenyl/Sulfinyl/Sulfonyl-β-Chloroacrylamide Derivatives to Form Densely Functionalised Pyrazoles [J].

Flynn, Aaran J. ;

Ford, Alan ;

Khandavilli, U. B. Rao ;

Lawrence, Simon E. ;

Maguire, Anita R. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (31-32) :5368-5384

[9] Bamford-Stevens and Shapiro Reactions in Organic Synthesis [J].

Ghavre, Mukund .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (12) :1901-1923

[10] Profiling the reactivity of cyclic C-nucleophiles towards electrophilic sulfur in cysteine sulfenic acid [J].

Gupta, Vinayak ;

Carroll, Kate S. .

CHEMICAL SCIENCE, 2016, 7 (01) :400-415

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