An efficient one-pot synthesis of 3-(aryl and alkyl)methylene-1H-isoindolin-1-ones via aryne cyclization and Horner reaction of o- (and m-)halogeno-N-phosphorylmethylbenzamide derivatives.

被引：91

作者：

Couture, A

Deniau, E

Grandclaudon, P

机构：

[1] Lab. de Chimie Organique Physique, URA CNRS 351, Univ. des Sci. et Technol. de Lille

来源：

TETRAHEDRON | 1997年 / 53卷 / 30期

关键词：

D O I：

10.1016/S0040-4020(97)00680-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 3-(alkyl and aryl)methylene-2,3-dihydro-1H-isoindol-1-one derivatives was synthesized by a one-pot reaction sequence involving lithiation of 2- (or 3-)halogeno-N-phosphoryl-methylbenzamides, cyclization of the aryne intermediate, metal migration and Horner reaction of the resulting phosphorylated aminocarbanion with selected aromatic and aliphatic aldehydes. (C) 1997 Elsevier Science Ltd.

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页码：10313 / 10330

页数：18

相关论文

共 84 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].

AbdelMagid, AF ;

Carson, KG ;

Harris, BD ;

Maryanoff, CA ;

Shah, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862

[2] CONFIGURATION OF ALKYLIDENEPHTHALIMIDINE DERIVATIVES [J].

ANG, WS ;

HALTON, B .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1971, 24 (04) :851-&

[3]

[Anonymous], 1991, J.P.H. Patent, Patent No. [03,133,955, 03133955]

[4] 2-(DIPHENYLPHOSPHINOYL) PYRROLIDINES - VERSATILE REAGENTS FOR THE SYNTHESIS OF HETEROCYCLIC ENAMINES AND ENAMIDES [J].

BAKKER, BH ;

ALIM, DST ;

VANDERGEN, A .

TETRAHEDRON LETTERS, 1984, 25 (38) :4259-4262

[5] INTRAMOLECULAR CYCLIZATIONS OF ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - CONVENIENT SYNTHESES OF 3-MEMBERED-RING, 5-MEMBERED-RING, AND 6-MEMBERED-RING HETEROCYCLIC NITROGEN-COMPOUNDS AND ELABORATIONS OF 3-MEMBERED RING-SYSTEMS [J].

BEAK, P ;

WU, SD ;

YUM, EK ;

JUN, YM .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (02) :276-277

[6] DIPOLE-STABILIZED CARBANIONS - NOVEL AND USEFUL INTERMEDIATES [J].

BEAK, P ;

REITZ, DB .

CHEMICAL REVIEWS, 1978, 78 (03) :275-316

[7] METALATION AND ELECTROPHILIC SUBSTITUTION OF AMINE DERIVATIVES ADJACENT TO NITROGEN - ALPHA-METALLO AMINE SYNTHETIC EQUIVALENTS [J].

BEAK, P ;

ZAJDEL, WJ ;

REITZ, DB .

CHEMICAL REVIEWS, 1984, 84 (05) :471-523

[8] Metalation of nitroaromatics with in situ electrophiles [J].

Black, WC ;

Guay, B ;

Scheuermeyer, F .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03) :758-760

[9] VINYL AZIDES IN HETEROCYCLIC SYNTHESIS .8. SYNTHESIS OF THE NATURALLY-OCCURRING PHOSPHODIESTERASE INHIBITORS PDE-I AND PDE-II [J].

BOLTON, RE ;

MOODY, CJ ;

REES, CW ;

TOJO, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (04) :931-935

[10]

BROEKHOF NLJ, 1984, RECL TRAV CHIM PAY B, V103, P311

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