A Clean and Expedient Synthesis of Pyrido[1,4]oxazepino Spiropyrrolidines Through One-Pot, Three-Component [3+2] Cycloaddition Reaction

被引：2

作者：

Kathiravan, S. ^{[1
]}

Babu, A. R. Suresh ^{[1
]}

Raghunathan, R. ^{[1
]}

机构：

[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India

来源：

SYNTHETIC COMMUNICATIONS | 2010年 / 40卷 / 24期

关键词：

Azomethine ylide; Baylis-Hillman adducts; cycloaddition; pyrido[1; 4]-oxazepine; spiropyrrolidine; AZOMETHINE YLIDES; ALKALOIDS;

D O I：

10.1080/00397910903531730

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

One-pot three component synthesis of novel pyrido[1,4]-oxazepine fused spiropyrrolidines has been accomplished in good yields by 1,3-dipolar cycloaddition reaction of azomethine ylide, derived from paraformaldehyde and sarcosine with (E)-4-benzylidene-hexahydro-1H-pyrido[2,1-c][1,4]-oxazepine-3(7H)-one as dipolarophiles derived from Baylis-Hillman adducts. The effect of solvent on the [3+2]-cycloaddition reaction is also studied.

引用

页码：3721 / 3727

页数：7

共 24 条

[1] Heteropolyacid-silica mediated [3+2] cycloaddition of azomethine ylides - a facile multicomponent one-pot synthesis of novel dispiroheterocycles [J].

Babu, A. R. Suresh ;

Raghunathan, R. .

TETRAHEDRON LETTERS, 2006, 47 (52) :9221-9225

[2] ZrOCl2•8H2O mediated microwave induced [3+2] cycloaddition of azomethine ylides -: a facile one-pot synthesis of novel dispiroheterocycles [J].

Babu, A. R. Suresh ;

Raghunathan, R. .

TETRAHEDRON LETTERS, 2007, 48 (02) :305-308

[3] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[4]

Braekman JC, 1999, EUR J ORG CHEM, V1999, P1749

[5] Synthesis and biological evaluation of five-membered heterocycles fused to cyclopenta[c]thiophene as new antitumor agents [J].

Dallemagne, P ;

Khanh, LP ;

Alsaïdi, A ;

Varlet, I ;

Collot, V ;

Paillet, M ;

Bureau, R ;

Rault, S .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (07) :1161-1167

[6] ALKALOIDS FROM DENDROBATID FROGS - STRUCTURES OF 2 OMEGA-HYDROXY CONGENERS OF 3-BUTYL-5-PROPYLINDOLIZIDINE AND OCCURRENCE OF 2,5-DISUBSTITUTED PYRROLIDINES AND A 2,6-DISUBSTITUTED PIPERIDINE [J].

DALY, JW ;

SPANDE, TF ;

WHITTAKER, N ;

HIGHET, RJ ;

FEIGL, D ;

NISHIMORI, N ;

TOKUYAMA, T ;

MYERS, CW .

JOURNAL OF NATURAL PRODUCTS, 1986, 49 (02) :265-280

[7] Dapson in Heterocyclic Chemistry, Part IV: Synthesis of Some Novel Diphenylsulfones Containing Acetamide, Pyrrolidine, Piperazine, and Thiomorpholine Moieties as Antimicrobial and Antitumor Agents [J].

Ghorab, M. M. ;

El Gaby, M. S. A. ;

Amin, N. E. ;

Taha, N. M. H. ;

Shehab, M. A. ;

Faker, I. M. I. .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (12) :2929-2942

[8] DECARBOXYLATIVE TRANSAMINATION - MECHANISM AND APPLICATIONS TO THE SYNTHESIS OF HETEROCYCLIC-COMPOUNDS [J].

GRIGG, R ;

THIANPATANAGUL, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (03) :180-181

[9] 1,8-naphthyridines V. Novel N-substituted 5-amino-N,N-diethyl-9-isopropyl [1,2,4]triazolo[4,3-a] [1,8]naphthyridine-6-carboxamides, as potent anti-inflammatory and/or analgesic agents completely devoid of acute gastrolesivity [J].

Grossi, G ;

Di Braccio, M ;

Roma, G ;

Ballabeni, V ;

Tognolini, M ;

Barocelli, E .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (02) :155-165

[10] Design, synthesis, and evaluation of new chemosensitizers in multi-drug-resistant Plasmodium falciparum [J].

Guan, J ;

Kyle, DE ;

Gerena, L ;

Zhang, QA ;

Milhous, WK ;

Lin, AJ .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (13) :2741-2748

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