A Facile, One-Pot Synthesis of Functionalized Spiro-Oxindoles via Vinylogous Aldol Reaction of Vinyl Malononitriles with Isatin Derivatives in Aqueous Media

被引：35

作者：

Babu, Thelagathoti Hari ^{[1
]}

Karthik, K. ^{[1
]}

Perumal, Paramasivan T. ^{[1
]}

机构：

[1] Cent Leather Res Inst, Div Organ Chem, Madras 600020, Tamil Nadu, India

来源：

SYNLETT | 2010年 / 07期

关键词：

isatin; vinyl malononitrile; vinylogous aldol condensation; one-pot tandem reaction; spirocyclic oxindoles; RUTHENIUM AMIDO COMPLEXES; STEREOSELECTIVE-SYNTHESIS; TRANSFER HYDROGENATION; BETA-LACTAM; SPIROOXINDOLES; ALKALOIDS; SPIROTRYPROSTATIN; CYCLOADDITION; CONVENIENT; ALKENES;

D O I：

10.1055/s-0029-1219588

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel, one-pot approach to functionalized spirocyclic oxindoles has been developed by using vinyl malononitriles and isatin derivatives via vinylogous aldol reaction in aqueous media catalyzed by triethylamine.

引用

页码：1128 / 1132

页数：5

共 52 条

[1] Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences [J].

Alcaide, B ;

Almendros, P ;

Rodríguez-Acebes, R .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06) :2346-2351

[2] A novel method for the synthesis of functionalized spirocyclic oxindoles by one-pot tandem reaction of vinyl malononitriles with isatylidene malononitriles [J].

Babu, Thelagathoti Hari ;

Joseph, A. Abragam ;

Muralidharan, D. ;

Perumal, Paramasivan T. .

TETRAHEDRON LETTERS, 2010, 51 (06) :994-996

[3] A facile one-pot synthesis of N-substituted tetrahydroquinolines [J].

Babu, Thelagathoti Hari ;

Shanthi, Gnanamani ;

Perumal, Paramasivan T. .

TETRAHEDRON LETTERS, 2009, 50 (24) :2881-2884

[4] Total synthesis of spirotryprostatin B via asymmetric nitroolefination [J].

Bagul, TD ;

Lakshmaiah, G ;

Kawabata, T ;

Fuji, K .

ORGANIC LETTERS, 2002, 4 (02) :249-251

[5] TiCl4 catalyzed tandem construction of C-C and C-O bonds:: a simple and one-pot atom-economical stereoselective synthesis of spiro-oxindoles [J].

Basavaiah, D ;

Rao, JS ;

Reddy, RJ ;

Rao, AJ .

CHEMICAL COMMUNICATIONS, 2005, (20) :2621-2623

[6] Organocatalytic regio- and asymmetric C-selective SNAr reactions-stereoselective synthesis of optically active spiro-pyrrolidone-3,3′-oxoindoles [J].

Bella, M ;

Kobbelgaard, S ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) :3670-3671

[7] Vinylogous Mannich reactions: selectivity and synthetic utility [J].

Bur, SK ;

Martin, SF .

TETRAHEDRON, 2001, 57 (16) :3221-3242

[8]

Carey F. A., 2000, ADV ORG CHEM, P57

[9] The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver [J].

Casiraghi, G ;

Zanardi, F ;

Appendino, G ;

Rassu, G .

CHEMICAL REVIEWS, 2000, 100 (06) :1929-1972

[10] Convergent diversity-oriented synthesis of small-molecule hybrids [J].

Chen, C ;

Li, XD ;

Neumann, CS ;

Lo, MMC ;

Schreiber, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) :2249-2252

← 1 2 3 4 5 6 →