A novel and facile synthesis of functionalized [4.4.3] and [4.4.4] propellano-bislactones using acetates of the Baylis-Hillman adducts

被引:63
作者
Basavaiah, D [1 ]
Satyanarayana, T [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
关键词
D O I
10.1021/ol016469w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A simple and convenient synthesis of 11,16-di[(E)-arylidene]-13,14-dioxatetracyclo-[7.4.4.0.(1,9)0(2,7)]heptadeca-2,4,6-trione-12,15-diones and 12,17-di[(E)-benzylidene]-14,15-dioxatetracyclo[8.4.4.0.(1,10)0(2,7)]octadeca-2,4,6-triene-13,16-dione, i.e., 2,10-dioxa[4.4.3]propellane-3,9-diones and 2,10-dioxa[4.4.4] propellane-3,9-dione, using acetates of the Baylis-Hillman adducts has been described.
引用
收藏
页码:3619 / 3622
页数:4
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共 36 条
[1]   Metal- and ligand-accelerated catalysis of the Baylis-Hillman reaction [J].
Aggarwal, VK ;
Mereu, A ;
Tarver, GJ ;
McCague, R .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7183-7189
[2]   STRUCTURE AND CONFORMATION OF HETEROCYCLES .21. PROBING THE ANOMERIC EFFECT IN ORTHOESTERS - STRUCTURE, CONFORMATION, AND DYNAMIC BEHAVIOR OF A UNIQUE ORTHOOXALATE - 2,5,7,10,11,14-HEXAOXA[4.4.4]PROPELLANE [J].
APED, P ;
FUCHS, B ;
GOLDBERG, I ;
SENDEROWITZ, H ;
TARTAKOVSKY, E ;
WEINMAN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5585-5590
[3]   PROPELLANES .80. BAEYER-VILLIGER OXIDATION OF [4.3.3]PROPELLANE-8,11-DIONE .79. [J].
ASHKENAZI, P ;
KAPON, M ;
PIANTINI, U ;
VONPHILIPSBORN, W ;
GINSBURG, D .
HELVETICA CHIMICA ACTA, 1985, 68 (03) :614-617
[4]   Asymmetric Baylis-Hillman reactions: catalysis using a chiral pyrrolizidine base [J].
Barrett, AGM ;
Cook, AS ;
Kamimura, A .
CHEMICAL COMMUNICATIONS, 1998, (22) :2533-2534
[5]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[6]   One-pot inter- and intramolecular Friedel-Crafts reactions in Baylis-Hillman chemistry:: a novel facile synthesis of (E)-2-arylideneindan-1-ones [J].
Basavaiah, D ;
Reddy, RM .
TETRAHEDRON LETTERS, 2001, 42 (16) :3025-3027
[7]   The Baylis-Hillman chemistry in aqueous media: a convenient synthesis of 2-methylenealkanoates and alkanenitriles [J].
Basavaiah, D ;
Kumaragurubaran, N .
TETRAHEDRON LETTERS, 2001, 42 (03) :477-479
[8]   Baylis-Hillman chemistry: a novel synthesis of functionalized 1,4-pentadienes [J].
Basavaiah, D ;
Kumaragurubaran, N ;
Sharada, DS .
TETRAHEDRON LETTERS, 2001, 42 (01) :85-87
[9]   A facile one-pot conversion of acetates of the Baylis-Hillman adducts to [E]-α-methylcinnamic acids [J].
Basavaiah, D ;
Krishnamacharyulu, M ;
Hyma, RS ;
Sarma, PKS ;
Kumaragurubaran, N .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1197-1200