A high temperature investigation using microwave synthesis for electronically and sterically disfavoured substrates of the Newman-Kwart rearrangement

被引：42

作者：

Moseley, Jonathan D. ^{[1
]}

Lenden, Philip ^{[1
]}

机构：

[1] AstraZeneca, Proc Res & Dev, Bristol BS10 7ZE, Avon, England

来源：

TETRAHEDRON | 2007年 / 63卷 / 19期

关键词：

microwave; Newman-Kwart; rearrangement;

D O I：

10.1016/j.tet.2007.02.101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electronically deactivated and/or sterically hindered substrates undergo the Newman-Kwart rearrangement (NKR) at around 300 degrees C, beyond the range of most convenient and safe, small-scale laboratory equipment. We report here the convenient conversions of several difficult substrates using modern microwave technology, which has proven ideal for investigating this high temperature reaction in all but the most refractory of cases. In addition, several previously reported difficult examples were re-investigated, and found not to require high temperatures under these conditions, for various reasons which are elaborated upon. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：4120 / 4125

页数：6

共 43 条

[1] Roles of water for chemical reactions in high-temperature water [J].

Akiya, N ;

Savage, PE .

CHEMICAL REVIEWS, 2002, 102 (08) :2725-2750

[2]

[Anonymous], 1997, ORGANIC SYNTHESIS WA

[3]

[Anonymous], UNPUB

[4] A new approach to rapid parallel development of four neurakinin antagonists. Part 4. Synthesis of ZD2249 methoxy sulfoxide [J].

Bowden, SA ;

Burke, JN ;

Gray, F ;

McKown, S ;

Moseley, JD ;

Moss, WO ;

Murray, PM ;

Welham, MJ ;

Young, MJ .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2004, 8 (01) :33-44

[5] Controlled synthesis and reversible oxidation of a thiolate-bridged macrocyclic dinickel(II) complex [J].

Brooker, S ;

Croucher, PD ;

Roxburgh, FM .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1996, (14) :3031-3037

[6] SODIUM ARYLSULFONATES FROM PHENOLS [J].

COOPER, JE ;

PAUL, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) :2046-&

[7] SODIUM ALKYLBENZENESULFONATES FROM PHENOLS [J].

COOPER, JE ;

PAUL, JM .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1970, 15 (04) :586-&

[8]

CORRAL C, 1984, SYNTHESIS-STUTTGART, P172

[9] Synthesis of structurally modified atropisomeric biaryl dithiols. Observations on the Newman-Kwart rearrangement [J].

Cossu, S ;

DeLucchi, O ;

Fabbri, D ;

Valle, G ;

Painter, GF ;

Smith, RAJ .

TETRAHEDRON, 1997, 53 (17) :6073-6084

[10] SYNTHESIS OF 4-(2-HYDROXYETHYLSULFONYL)-1-NAPHTHALENESULFONAMIDE [J].

DAUB, GH ;

WHALEY, TW .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (24) :4659-4662

← 1 2 3 4 5 →