An efficient one-pot synthesis of pyrimido[2,1-b][1,3]thiazine derivatives by reaction of activated acetylenes, thiouracils, and isocyanides

被引：26
作者：
Baharfar, Robabeh [1 ]
Baghbanian, Seyed Meysam [1 ]
Vahdat, Seyed Mohammad [2 ]
机构：
[1] Univ Mazandaran, Dept Chem, Babol Sar, Iran
[2] Islamic Azad Univ, Ayatollah Amoli Branch, Dept Chem, Amol, Iran
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 45期
关键词：
Pyrimido[2,1-b][1,3]thiazines; Isocyanides; Activated acetylenes; Multicomponent reaction; PYRIMIDINE; ACIDS;
D O I：
10.1016/j.tetlet.2011.09.008
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reactive 1:1 zwitterionic intermediate, formed by the addition of isocyanides to dialkyl acetylenedi-carboxylates, was trapped by thiouracils to yield a ketenimine intermediate, which cyclized and then rearranged to afford pyrimido[2,1-b][1,3]thiazines in good yields. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6018 / 6020
页数：3
相关论文
共 31 条
[1]   Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of 2,4-dihydro-3H-pyrazol-3-ones.: One-pot syntesis of highly functionalized 7-oxo-1H,7H-pyrazolo[1,2-α]pyrazoles [J].
Adib, M ;
Sayahi, MH ;
Aghaaliakbari, B ;
Bijanzadeh, HR .
TETRAHEDRON, 2005, 61 (16) :3963-3966
[2]   SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF A SERIES OF ANTIBACTERIALLY ACTIVE 5-(5-NITRO-2-FURFURYLIDENE)THIAZOLONES, 5-(5-NITRO-2-FURYLPROPENYLIDENE)THIAZOLONES, AND 6-(5-NITRO-2-FURYL)-H-4-1,3-THIAZIONES [J].
AKERBLOM, EB .
JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (06) :609-615
[3]   Competition of the R3P/DAAD and RNC/DAAD zwitterions in their production and reaction with aromatic carboxylic acids:: A novel binucleophilic system for three-component synthesis of 2-aminofurans [J].
Alizadeh, Abdolali ;
Rostamnia, Sadegh ;
Zhu, Long-Guan .
SYNTHESIS-STUTTGART, 2008, (11) :1788-1792
[4]  
Baharfar R., 2011, J HETEROCYC IN PRESS
[5]  
Baharfar R., 2011, PHOSPHORUS IN PRESS
[6]  
Baharfar R., 2008, ACTA CRYSTALLOGR E, VE64, P01203
[7]   A novel approach to the synthesis of highly functionalized thiophenes using isocyanides catalyzed reaction of acetylenic esters with 3-mercapto-2-butanone [J].
Baharfar, Robabeh ;
nia, Roghayeh Hossein ;
Baghbanian, Seyed Meysam .
LETTERS IN ORGANIC CHEMISTRY, 2008, 5 (02) :128-132
[8]   The novel one-pot synthesis of functionalized vinyl sulfides using triphenylphosphine catalyzed nucleophilic addition of thiols to acetylenes [J].
Baharfar, Robabeh ;
Baghbanian, Seyed M. ;
Hossein nia, Roghayeh ;
Bijanzadeh, Hamid R. .
LETTERS IN ORGANIC CHEMISTRY, 2007, 4 (08) :567-570
[9]  
Baharfar R, 2007, LETT ORG CHEM, V4, P429
[10]   An efficient multicomponent transformation of alkyl isocyanides, dialkyl acetylenedicarboxylates, and 2,4-dihydroxybenzophenones or 2,4-dihydroxyacetophenones into 2-amino-4H-chromene derivatives [J].
Baharfar, Robabeh ;
Vahdat, Seyed Mohammad ;
Ahmadian, Majid ;
Taghizadeh, Mohammad Javad .
MONATSHEFTE FUR CHEMIE, 2010, 141 (02) :213-218
1234