Photodecarboxylative benzylations of phthalimide in pH 7 buffer: a simple access to 3-arylmethyleneisoindolin-1-ones

被引：45

作者：

Belluau, Vincent ^{[1
]}

Noeureuil, Pierre ^{[2
]}

Ratzke, Elfrun ^{[1
]}

Skvortsov, Aleksei ^{[1
]}

Gallagher, Sonia ^{[2
]}

Motti, Cherri Ann ^{[3
]}

Oelgemoeller, Michael ^{[1
]}

机构：

[1] James Cook Univ, Sch Pharm & Mol Sci, Townsville, Qld 4811, Australia

[2] Dublin City Univ, Sch Chem Sci, Dublin 9, Ireland

[3] Australian Inst Marine Sci, Biomol Anal Facil, Townsville, Qld 4810, Australia

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 36期

基金：

爱尔兰科学基金会;

关键词：

Photodecarboxylation; Benzylation; Phthalimide; Photochemistry; Micro-photochemistry; Isoindolinones; ALPHA-KETO CARBOXYLATES; ONE-POT SYNTHESIS; PHOTOCHEMICAL DECARBOXYLATION; STEREOSELECTIVE-SYNTHESIS; N-ALKYLPHTHALIMIDES; CYCLIZATION; SPECTROSCOPY; ADDITIONS; ROUTE; ACIDS;

D O I：

10.1016/j.tetlet.2010.07.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photoadditions of phenylacetates to phthalimide in pH 7 buffer solution give the corresponding benzylated-hydroxyphthalimidines in moderate to high yields of up to 94%. In a micro-structured reactor, higher conversions and purities are achieved. With branched phenylacetates, photoaddition affords diastereoisomeric mixtures with low to moderate de values. Subsequent acid-catalyzed dehydration furnishes the corresponding 3-arylmethyleneisoindolin-1-ones in good to excellent yields and with high E-selectivities. Irradiation of the parent 3-phenylmethyleneisoindolin-1-one under oxidative conditions only leads to cis/trans-isomerization. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4738 / 4741

页数：4

共 50 条

[11] Photodecarboxylative additions of N-protected α-amino acids to N-methylphthalimide [J].

Gallagher, Sonia ;

Hatoum, Fadi ;

Zientek, Nicolai ;

Oelgemoeller, Michael .

TETRAHEDRON LETTERS, 2010, 51 (28) :3639-3641

[12] Photodecarboxylation study of carboxy-substituted N-alkylphthalimides in aqueous solution:: Time resolved UV-vis spectroscopy and conductometry [J].

Görner, H ;

Oelgemöller, M ;

Griesbeck, AG .

JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (07) :1458-1464

[13]

Görner H, 2001, CHEM-EUR J, V7, P1530

[14] Photodecarboxylative benzylation of N-alkylphthalimides:: A concise route to the aristolactam skeleton [J].

Griesbeck, AG ;

Warzecha, KD ;

Neudöfl, JM ;

Görner, H .

SYNLETT, 2004, (13) :2347-2350

[15] The excimer radiation system:: a powerful tool for preparative organic photochemistry.: A technical note [J].

Griesbeck, AG ;

Maptue, N ;

Bondock, S ;

Oelgemöller, M .

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2003, 2 (04) :450-451

[16] Synthesis of cyclic peptides by photochemical decarboxylation of N-phthaloyl peptides in aqueous solution [J].

Griesbeck, AG ;

Heinrich, T ;

Oelgemöller, M ;

Molis, A ;

Heidtmann, A .

HELVETICA CHIMICA ACTA, 2002, 85 (12) :4561-4578

[17] A photochemical route for efficient cyclopeptide formation with a minimum of protection and activation chemistry [J].

Griesbeck, AG ;

Heinrich, T ;

Oelgemöller, M ;

Lex, J ;

Molis, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (37) :10972-10973

[18]

Griesbeck AG, 2000, SYNLETT, P1455

[19] Synthesis of medium- and large-ring compounds initiated by photochemical decarboxylation of omega-phthalimidoalkanoates [J].

Griesbeck, AG ;

Henz, A ;

Kramer, W ;

Lex, J ;

Nerowski, F ;

Oelgemoller, M ;

Peters, K ;

Peters, EM .

HELVETICA CHIMICA ACTA, 1997, 80 (03) :912-933

[20]

Griesbeck AG, 1999, SYNLETT, P492

← 1 2 3 4 5 →