Efficient One-Pot Synthesis of Precursors of Some Novel Aminochromene Annulated Heterocycles via Domino Knoevenagel-hetero-Diels-Alder Reaction

被引：5

作者：

Parmar, Narsidas J. ^{[1
]}

Teraiya, Shashikant B. ^{[1
]}

Barad, Hitesh A. ^{[1
]}

Sharma, Deepak ^{[2
]}

Gupta, Vivek K. ^{[2
]}

机构：

[1] Sardar Patel Univ, Dept Chem, Vallabh Vidyanagar 388120, Gujarat, India

[2] Univ Jammu, Postgrad Dept Phys, Jammu, India

来源：

SYNTHETIC COMMUNICATIONS | 2013年 / 43卷 / 11期

关键词：

Aminochromene; 1; 3-diketone; polyheterocycles; TBA-HS; xanthene; DERIVATIVES;

D O I：

10.1080/00397911.2011.652755

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, one-pot synthetic approach to precursors of some new aminochromene/xanthene annulated heterocycles via a tetrabutylammonium hydrogen sulfate-mediated intramolecular domino Knoevenagel-hetero-Diels-Alder reaction is described. The method is general and efficient. The stereochemistry of the product was confirmed by various NMR experiments and single-crystal x-ray diffraction data. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

引用

页码：1577 / 1586

页数：10

共 30 条

[21]

POUPELIN JP, 1978, EUR J MED CHEM, V13, P67

[22] Microwave-Assisted K-10 Montmorillonite Clay-Mediated Knoevenagel Hetero-Diels-Alder Reactions: A Novel Protocol for the Synthesis of Polycyclic Pyrano[2,3,4-kl]xanthene Derivatives [J].

Ramesh, Ekambaram ;

Raghunathan, Raghavachary .

SYNTHETIC COMMUNICATIONS, 2009, 39 (04) :613-625

[23] First examples of proline-catalyzed domino Knoevenagel/hetero-Diels-Alder/elimination reactions [J].

Sabitha, G ;

Fatima, N ;

Reddy, EV ;

Yadav, JS .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (10) :1353-1355

[24] High chemoselectivity in microwave accelerated intramolecular domino Knoevenagel hetero Diels-Alder reactions - an efficient synthesis of pyrano[3-2c]coumarin frameworks [J].

Shanmugasundaram, M ;

Manikandan, S ;

Raghunathan, R .

TETRAHEDRON, 2002, 58 (05) :997-1003

[25]

Tietze LF, 2000, MED RES REV, V20, P304, DOI 10.1002/1098-1128(200007)20:4<304::AID-MED3>3.3.CO

[26]

2-#

[27]

Tietze LF, 1998, CURR ORG CHEM, V2, P19

[28] INTERMOLECULAR AND INTRAMOLECULAR HETERO-DIELS-ALDER REACTIONS .20. STEREOCONTROLLED FORMATION OF ANNELATED CYCLOPENTANES BY INTRAMOLECULAR HETERO-DIELS-ALDER REACTION - SYNTHESIS OF DEOXYLOGANIN FROM CITRONELLAL [J].

TIETZE, LF ;

DENZER, H ;

HOLDGRUN, X ;

NEUMANN, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (12) :1295-1297

[29] Domino reactions in organic synthesis [J].

Tietze, LF .

CHEMICAL REVIEWS, 1996, 96 (01) :115-136

[30]

Zhu J, 2005, MULTICOMPONENT REACTIONS, P1, DOI 10.1002/3527605118

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