New Efficient Synthesis of 1,2,4-Trisubstituted Furans by a ­Sequential Passerini/Wittig/Isomerization Reaction Starting from Baylis–Hillman β-Bromo Aldehydes

Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 106-110 ◽  
Author(s):  
Ming-Wu Ding ◽  
Zhi-Lin Ren ◽  
Mei Sun ◽  
Zhi-Rong Guan

A new and efficient synthesis of 1,2,4-trisubstituted furans from a Baylis–Hillman β-bromo aldehyde, an acid, an isocyanide, and methyl(diphenyl)phosphine, by a sequential Passerini condensation, Wittig reaction, and isomerization in the presence of triethylamine is reported.

2009 ◽  
Vol 56 (1) ◽  
pp. 47-50 ◽  
Author(s):  
Li-Qiang Wu ◽  
Chun-Guang Yang ◽  
Li-Ming Yang ◽  
Li-Juan Yang

2013 ◽  
Vol 8 (8) ◽  
pp. 1934578X1300800
Author(s):  
Dandan Xu ◽  
Ying Nie ◽  
Xizhou Liang ◽  
Ling Ji ◽  
Songyuan Hu ◽  
...  

The concise, efficient synthesis of α-mangostin is described in eight simple steps with 8.3% overall yield. Highlights include a practical approach to construct the isopentene groups and other diverse groups at C–2 and C–8 of the xanthene skeleton through Claisen rearrangement and Wittig reaction. Meanwhile the first total synthesis of β-mangostin is presented with a similar approach.


2017 ◽  
Vol 47 (6) ◽  
pp. 581-589 ◽  
Author(s):  
Tushar R. Valkute ◽  
Eswar K. Aratikatla ◽  
Asish K. Bhattacharya

2012 ◽  
Vol 455-456 ◽  
pp. 655-659
Author(s):  
Hong Chen ◽  
Kai Yan ◽  
Ming Guo Liu

The carbodiimides 4, obtained from the aza-Wittig reaction of iminophosphorane 3 with aromatic isocyanates, reacted with aliphatic amines or alcohols to give 2-substituted thieno [2,3-d] pyrimidin-4(4H)-ones 6 in the presence of catalytic amount of sodium alkoxide in good yields.


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