CONVENIENT SYNTHESIS OF 2,2-DIMETHYL-3,4-DIHYDRO-2H-PYRANO[2,3-B]QUINOLINES

被引：1
|
作者：
Parsekar, Sonia B. [1 ]
Amonkar, Chandan P. [1 ]
Parameswaran, Peruninakulath S. [2 ]
Tilve, Santosh G. [1 ]
机构：
[1] Goa Univ, Dept Chem, Goa 403206, India
[2] Natl Inst Oceanog, Panaji, Goa, India
来源：
SYNTHETIC COMMUNICATIONS | 2010年 / 40卷 / 21期
关键词：
Domino reaction; lactones; pyranoquinoline; reductive cyclization; Wittig reaction; BALFOURODENDRON-RIEDELIANUM; WITTIG REACTION; QUINOLINE; ALKALOIDS; AGENTS;
D O I：
10.1080/00397910903398668
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient general synthesis of 2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]quinolines using the Wittig reaction is described. The o-nitrobenzaldehydes (1a-d) on reaction with phosphorane 2 provided (E)-ethyl--(2,2-dimethylprop-2-ene)-2-nitrocinnamates (3a-d) in excellent yields, which on cyclization with polyphosphoric acid followed by reductive cyclization using Fe/HCl afforded dihydropyranoquinolines (5a-d). Alternatively, the pyranoquinolines 5a-d were also synthesised from esters 3a-d by employing domino reductive cyclization in a single step.
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收藏
页码：3251 / 3258
页数：8
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