Phosphonium-mediated synthesis of a new class of indoloquinazoline derivatives bearing C-12 aryloxy ester and spiro-γ-lactone

Synthesis ◽  
2021 ◽  
Author(s):  
Nittaya Wiriya ◽  
Mookda Pattarawarapan ◽  
Saranphong Yimklan ◽  
Surat Hongsibsong ◽  
Wong Phakhodee

Indoloquinazolines functionalized at C-12 which are structure analogs of the natural alkaloid cephalanthrin B were readily constructed via a Ph3P-I2 mediated one-pot reaction of isatins with aromatic alcohols. In the presence of excess phenols, the C-12 aryloxy ester products were afforded in moderate to good yields under mild conditions. Moreover, fused bicyclic hydroxyaryl derivatives such as 8-hydroxyquinoline gave rise to novel C-12 spiro-γ-lactone derivatives. Reactive iminium cation species derived from dehydration of the C-12 hydroxy ester precursor is proposed to be transient intermediates responsible for these unprecedented transformations.

2018 ◽  
Vol 47 (32) ◽  
pp. 10915-10924 ◽  
Author(s):  
Xiangju Ye ◽  
Yinghao Chen ◽  
Cancan Ling ◽  
Ran Ding ◽  
Xuchun Wang ◽  
...  

The use of solar energy to drive organic reactions under mild conditions provides a sustainable pathway for green synthesis and has been one of the primary goals pursued by scientists.


2021 ◽  
Vol 45 (7) ◽  
pp. 3479-3484
Author(s):  
Mohammad Taghi Nazeri ◽  
Ali Beygzade Nowee ◽  
Ahmad Shaabani

In this study, an efficient one-pot reaction is reported for the synthesis of a new class of pseudopeptide connected to sulfonamide via a tandem N-sulfonylation/Ugi four-component reaction (Ugi-4CR) strategy under mild conditions in high yields.


RSC Advances ◽  
2016 ◽  
Vol 6 (92) ◽  
pp. 89413-89416 ◽  
Author(s):  
Jiajia Gu ◽  
Zheng Fang ◽  
Yuhang Yang ◽  
Zhao Yang ◽  
Li Wan ◽  
...  

Copper-catalyzed one-pot oxidative amidation of both aliphatic and aromatic alcohols with N-chloramines, prepared in situ from many types of primary and secondary amines, to form amides under mild conditions.


2013 ◽  
Vol 16 (10) ◽  
pp. 788-790
Author(s):  
Zinatossadat Hossaini ◽  
Samereh Seyfi ◽  
Faramarz Rostami-Charati ◽  
Mehdi Ghambarian

Author(s):  
Philipp Natho ◽  
Zeyu Yang ◽  
Lewis Allen ◽  
Juliette Rey ◽  
Andrew J P White ◽  
...  

A transition-metal-free strategy for the synthesis of 2-(cyclobut-1-en-1-yl)-1H-indoles under mild conditions is described herein. A series of substituted 2-(cyclobut-1-en-1-yl)-1H-indoles are accessed by a one-pot cyclobutenylation/deprotection cascade from N-Boc protected indoles....


RSC Advances ◽  
2021 ◽  
Vol 11 (24) ◽  
pp. 14755-14768
Author(s):  
Malihe Akhavan ◽  
Ahmadreza Bekhradnia

An efficient, green, one-pot, and three-component protocol has been reported for the stereoselective synthesis of a new class of spiro thiazolidines.


2007 ◽  
Vol 48 (10) ◽  
pp. 1809-1811 ◽  
Author(s):  
Christopher A. Simoneau ◽  
Alexis M. Strohl ◽  
Bruce Ganem

2017 ◽  
Vol 4 (8) ◽  
pp. 1636-1639 ◽  
Author(s):  
Bin Cheng ◽  
Bian Bao ◽  
Yanhe Chen ◽  
Ning Wang ◽  
Yun Li ◽  
...  

A new route to arylhydrazides involving the reaction of two highly active intermediates, the 1,3-zwitterion generated in situ from the Mitsunobu reagent and arynes, under mild conditions has been developed.


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