Ultrasound-assisted synthesis of substituted guanidines from thioureas

被引:19
作者
Pattarawarapan, Mookda [1 ]
Jaita, Subin
Wangngae, Sirilak
Phakhodee, Wong
机构
[1] Chiang Mai Univ, Dept Chem, Fac Sci, Chiang Mai 50200, Thailand
关键词
Guanidine; Thiourea; Cyanuric chloride; Triphenylphosphine; Ultrasound; HGCL2-PROMOTED GUANYLATION REACTION; SOLID-PHASE SYNTHESIS; EFFICIENT GUANYLATION; ORGANIC-SYNTHESIS; AMINES; 2,4,6-TRICHLORO-1,3,5-TRIAZINE; CARBODIIMIDES; CHEMISTRY;
D O I
10.1016/j.tetlet.2016.02.050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ultrasound-assisted synthesis of guanidine derivatives was developed using 2,4,6-trichloro-1,3,5-triazine as an inexpensive dehydrosulfurization reagent. Both 1,3-alkylaryl- and 1,3-diaryl-thioureas were rapidly converted into carbodiimides before subsequent reaction with aromatic or aliphatic amines. The method allows rapid access to highly substituted guanidines in good to excellent yields under mild conditions and with minimal use of solvent. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1354 / 1358
页数:5
相关论文
共 43 条
[1]   Green chemistry: A facile synthesis of polyfunctionally substituted thieno[3,4-c]pyridinones and thieno[3,4-d]pyridazinones under neat reaction conditions [J].
Al-Zaydi, Khadijah M. ;
Borik, Rita M. ;
Mekheimer, Ramadan A. ;
Elnagdi, Mohamed H. .
ULTRASONICS SONOCHEMISTRY, 2010, 17 (05) :909-915
[2]   Guanidines: from classical approaches to efficient catalytic syntheses [J].
Alonso-Moreno, Carlos ;
Antinolo, Antonio ;
Carrillo-Hermosilla, Fernando ;
Otero, Antonio .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (10) :3406-3425
[3]   Alternative energy input: mechanochemical, microwave and ultrasound-assisted organic synthesis [J].
Baig, R. B. Nasir ;
Varma, Rajender S. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (04) :1559-1584
[4]   The chemistry and biology of organic guanidine derivatives [J].
Berlinck, Roberto G. S. ;
Trindade-Silva, Amaro E. ;
Santos, Mario F. C. .
NATURAL PRODUCT REPORTS, 2012, 29 (12) :1382-1406
[5]   The chemistry and biology of organic guanidine derivatives [J].
Berlinck, Roberto G. S. ;
Burtoloso, Antonio Carlos B. ;
Trindade-Silva, Amaro E. ;
Romminger, Stelamar ;
Morais, Raquel P. ;
Bandeira, Karin ;
Mizuno, Carolina M. .
NATURAL PRODUCT REPORTS, 2010, 27 (12) :1871-1907
[6]   Recent applications of 2,4,6-trichloro-1,3,5-triazine and its derivatives in organic synthesis [J].
Blotny, Grzegorz .
TETRAHEDRON, 2006, 62 (41) :9507-9522
[7]   Modular three-component solid-phase synthesis of unsymmetrical guanidines via resin capture of carbodiimides [J].
Boguszewski, PA ;
Rahman, SS ;
Ganesan, A .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (01) :32-34
[8]   RECENT ADVANCES IN ORGANIC-SYNTHESIS UTILIZING ULTRASOUND [J].
BREMNER, DH .
ULTRASONICS SONOCHEMISTRY, 1994, 1 (02) :S119-S124
[9]   Solution- and solid-phase syntheses of substituted guanidinocarboxylic acids [J].
Chen, J ;
Pattarawarapan, M ;
Zhang, AJ ;
Burgess, K .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (03) :276-281
[10]   Power ultrasound in organic systhesis: moving cavitational chemistry from academia to innovative and large-scale applications [J].
Cravotto, G ;
Cintas, P .
CHEMICAL SOCIETY REVIEWS, 2006, 35 (02) :180-196