An exception to the normal Mitsunobu reaction with phenols; the formation of hydrazones from salicylaldehydes

被引：27

作者：

Girard, M

Murphy, P

Tsou, NN

机构：

[1] Merck Frosst Canada & Co, Dept Med Chem, Pointe Claire, PQ H9R 4P8, Canada

[2] Merck Res Labs, Rahway, NJ 07065 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 14期

关键词：

Mitsunobu; hydrazone; salicylaldehyde;

D O I：

10.1016/j.tetlet.2005.02.051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2-hydroxybenzaldehydes with alkanols in the presence of triphenylphosphine and di-tert-butyl azodicarboxylate (DBAD), under the Mitsunobu reaction conditions, gives rise to the formation of hydrazones as the major products rather than the expected alkyl aryl ethers. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2449 / 2452

页数：4

共 13 条

[1] AN EFFICIENT AND MILD CONDITIONS SYNTHESIS OF 2-AZA-1,3-DIENES FROM PHOSPHA-LAMBDA-5-AZENES [J].

BARLUENGA, J ;

FERRERO, M ;

PALACIOS, F .

TETRAHEDRON LETTERS, 1988, 29 (38) :4863-4864

[2]

BITTNER S, 1975, CHEM IND-LONDON, P281

[3]

CALABRETTA R, 1991, SYNTHESIS-STUTTGART, P536

[4] POLYPEPTIDES .13. PREPARATION OF ALPHA-AZA-AMINO-ACID (CARBAZIC ACID) DERIVATIVES AND INTERMEDIATES FOR PREPARATION OF ALPHA-AZA-PEPTIDES [J].

DUTTA, AS ;

MORLEY, JS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (17) :1712-1720

[5] THE MECHANISM OF THE MITSUNOBU REACTION - A P-31 NMR-STUDY [J].

GUTHRIE, RD ;

JENKINS, ID .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (04) :767-774

[6]

KATRITZKY AR, 1984, COMPREHENSIVE HETERO, V4, P337

[7]

KATRITZKY AR, 1984, COMPREHENSIVE HETERO, V4, P334

[8]

KATRITZKY AR, 1984, COMPREHENSIVE HETERO, V3, P41

[9]

KATRITZKY AR, 1984, COMPREHENSIVE HETERO, V7, P75

[10] STEROIDS .10. CONVENIENT SYNTHESIS OF ALKYL ARYL ETHERS [J].

MANHAS, MS ;

HOFFMAN, WH ;

LAL, B ;

BOSE, AK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (05) :461-463

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