Regioselective dihydropyran formation from 4-iodo-2,6-disubstituted tetrahydropyran derivatives using In(OAc)3/LiI system as the promoter

被引：2

作者：

Chalopin, Thibaut ^{[1
]}

Jebali, Khaoula ^{[1
,3
]}

Gaulon-Nourry, Catherine ^{[2
]}

Denes, Fabrice ^{[1
]}

Lebreton, Jacques ^{[1
]}

Mathe-Allainmat, Monique ^{[1
]}

机构：

[1] Univ Nantes, Fac Sci & Tech, Lab CEISAM, CNRS,UMR 6230, 2 Rue Houssiniere,BP 92208, F-44322 Nantes 3, France

[2] Univ Maine, CNRS, IMMM, UMR 6283, Ave O Messiaen, F-72085 Le Mans, France

[3] Univ Tunis El Manar, Fac Sci, Lab Select Organ Synth & Biol Act, Campus 2092, Tunis, Tunisia

来源：

TETRAHEDRON | 2016年 / 72卷 / 02期

关键词：

Oxygen heterocycles; Prins cyclization; Lewis acid; Elimination; Regioselectivity; PRINS-TYPE CYCLIZATION; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; COPE;

D O I：

10.1016/j.tet.2015.11.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rapid and regioselective synthesis of a series of 2,6-disubstituted dihydropyranic building-blocks bearing an oxygenated side chain is described. The corresponding 4-iodo tetrahydropyran precursors, easily prepared by Prins cyclization, underwent regioselective elimination in the presence of an In(OAc)(3)/LiI system to provide the title compounds. The one-pot Prins cyclization-elimination process was also studied and could be achieved with the TMSBr/Lil/In(OAc)(3) system. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：318 / 327

页数：10

共 4 条

[1] STEREOSPECIFIC AND STEREOSELECTIVE REACTIONS .10. REACTION OF 4,6-ORTHO-BENZYLIDENE-3-ORTHO-MESYL-ALLAL WITH ALLYLIC GRIGNARD-REAGENTS - HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE PREPARATION OF 2,6-DISUBSTITUTED DIHYDROPYRAN RINGS
OGIHARA, T
MITSUNOBU, O
TETRAHEDRON LETTERS, 1983, 24 (33) : 3505 - 3508
[2] Novel synthesis of 3,6-disubstituted-1,2,4,5-tetrazine derivatives from hydrazones by using [hydroxyl(tosyloxy)iodo]benzene
Liu, Haixuan
Wei, Yunyang
TETRAHEDRON LETTERS, 2013, 54 (35) : 4645 - 4648
[3] One-pot Synthesis of 2,3-disubstituted-4(3H)-quinazolinone from o-aminobenzoic Acid and DMF Derivatives using Imidazole Hydrochloride as a Promoter
Wang, Yin
Zhang, Xiuyu
Li, Suzhen
Guo, Mengyi
Ma, Wanqian
Yuan, Jianyong
CURRENT ORGANIC SYNTHESIS, 2024, 21 (07) : 957 - 963
[4] SYNTHESIS OF 7-SUBSTITUTED 5-OXO-5H-THIAZOLO[3,2-A]PYRIMIDINE-6-CARBOXYLIC ACIDS, 2-SUBSTITUTED 4-OXO-4H-PYRIDO[1,2-A]PYRIMIDINE-3-CARBOXYLIC ACIDS, AND 2,6-DISUBSTITUTED 4-QUINOLONES FROM MELDRUM ACID-DERIVATIVES
YE, FC
CHEN, BC
HUANG, X
SYNTHESIS-STUTTGART, 1989, (04): : 317 - 320

← 1 →