Michael-Type Adducts of 3-Carbethoxycoumarins via Diels-Alder Reaction: Tandem Ring Construction of Furopyranochroman-2-one Skeletons

被引：11

作者：

Prabhakar, Maddela ^{[1
]}

Reddy, G. Narendar ^{[1
]}

Srinu, G. ^{[1
]}

Manjulatha, K. ^{[1
]}

Prasad, J. Venkata ^{[1
]}

Kumar, S. Pramod ^{[1
]}

Srinivas, O. ^{[1
]}

Iqbal, Javed ^{[1
]}

Kumar, K. Anil ^{[1
]}

机构：

[1] Inst Life Sci, Hyderabad 500046, Andhra Pradesh, India

来源：

SYNLETT | 2010年 / 06期

关键词：

coumarins; substituted furans; fused furopyranochroman-2-ones; Michael products; Diels-Alder reaction; MCR; scaffold hopping reaction; COUMARINS; DERIVATIVES; CHEMISTRY;

D O I：

10.1055/s-0029-1219532

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder reaction of furan with electron-deficient 3-carbethoxycoumarins gave the Michael-type adducts obtained from the rearrangement of the intermediate Diels-Alder adducts, instead of the Diels-Alder cycloadducts. Trapping of the dipolar intermediate with electron-deficient aromatic aldehydes gave a one-pot access to fused furo[3,2-b]pyranochroman-2-ones with multiple stereogenic centers. Ring opening of the lactone moiety gave a facile route to generate diverse scaffolds.

引用

页码：947 / 951

页数：5

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