2-Aminoethanesulfonic acid: An efficient organocatalyst for green synthesis of spirooxindole dihydroquinazolinones and novel 1,2-(dihydroquinazolin-3(4H)isonicotinamides in water

被引:21
作者
Chate, Asha, V [1 ]
Rudrawar, Priyanka P. [1 ]
Bondle, Giribala M. [1 ]
Sangeshetti, Jaiprakash N. [2 ]
机构
[1] Dr Babasaheb Ambedkar Marathwada Univ, Dept Chem, Aurangabad 431004, Maharashtra, India
[2] YB Chavan Coll Pharm, Dept Qual Assurance, Rafiq Zakaria Campus, Aurangabad, Maharashtra, India
关键词
2-Aminoethanesulfonic acid (taurine); 2; 3-dihydroquinazolin-4(1H)-ones; multicomponent reaction; spirooxindole; ENANTIOSELECTIVE CONSTRUCTION; DIASTEREOSELECTIVE SYNTHESIS; SPIROCYCLIC OXINDOLES; ASYMMETRIC-SYNTHESIS; CATALYZED SYNTHESIS; DERIVATIVES; TAURINE; DESIGN; STEREOCENTERS; QUINAZOLINE;
D O I
10.1080/00397911.2019.1692868
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and efficient one-pot procedure for the preparation of spirooxindole dihydroquinazolinone derivatives and new N-(4-oxo-2-phenyl-1,2-dihydroquinazolin-3(4H)-yl)isonicotinamides from reaction between isatoic anhydride, isoniazid and substituted aldehydes catalyzed by 2-aminoethanesulfonic acid (taurine) is describe. This new protocol has the advantages of environmental friendliness, good yields, and convenient operation. The reaction proceeds efficiently using water as green solvent and nontoxic catalysts that could be efficiently reused. Together with this simple workup procedure, use of the organocatalyst, and water as solvent without the need of column chromatographic purification, are the notable features of this methodology, which make this protocol a very efficient and green alternative to the traditional methods.
引用
收藏
页码:226 / 242
页数:17
相关论文
共 90 条
[1]   Assembly of Spirooxindole Derivatives Containing Four Consecutive Stereocenters via Organocatalytic Michael-Henry Cascade Reactions [J].
Albertshofer, Klaus ;
Tan, Bin ;
Barbas, Carlos F., III .
ORGANIC LETTERS, 2012, 14 (07) :1834-1837
[2]  
Anastas P.T., 1998, Oxford University Press eBooks, P640, DOI DOI 10.1093/OSO/9780198506980.001.0001
[3]  
[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[4]   Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products [J].
Antonchick, Andrey P. ;
Gerding-Reimers, Claas ;
Catarinella, Mario ;
Schuermann, Markus ;
Preut, Hans ;
Ziegler, Slava ;
Rauh, Daniel ;
Waldmann, Herbert .
NATURE CHEMISTRY, 2010, 2 (09) :735-740
[5]   Taurine-nitrite interaction as a precursor of alkylation mechanisms [J].
Arenas-Valganon, Jorge ;
Gomez-Bombarelli, Rafael ;
Gonzalez-Perez, Marina ;
Gonzalez-Jimenez, Mario ;
Calle, Emilio ;
Casado, Julio .
FOOD CHEMISTRY, 2012, 134 (02) :986-991
[6]   Facile one-pot synthesis of novel dispirooxindole-pyrrolidine derivatives and their antimicrobial and anticancer activity against A549 human lung adenocarcinoma cancer cell line [J].
Arun, Y. ;
Bhaskar, G. ;
Balachandran, C. ;
Ignacimuthu, S. ;
Perumal, P. T. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (06) :1839-1845
[7]   One-step, synthesis of Hantzsch esters and polyhydroquinoline derivatives using new organocatalyst [J].
Baghbanian, Seyed Meysam ;
Khaksar, Samad ;
Vahdat, Seyed Mohammad ;
Farhang, Maryam ;
Tajbakhsh, Mahmood .
CHINESE CHEMICAL LETTERS, 2010, 21 (05) :563-567
[8]   Microwave activated synthesis of 2-aryl-qlainazolin-4(3H) ones [J].
Bakavoli, M. ;
Sabzevari, O. ;
Rahimizadeh, M. .
CHINESE CHEMICAL LETTERS, 2007, 18 (12) :1466-1468
[9]   Catalytic Enantioselective Carboannulation with Allylsilanes [J].
Ball-Jones, Nicolas R. ;
Badillo, Joseph J. ;
Tran, Ngon T. ;
Franz, Annaliese K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9462-9465
[10]   Strategies for the enantioselective synthesis of spirooxindoles [J].
Ball-Jones, Nicolas R. ;
Badillo, Joseph J. ;
Franz, Annaliese K. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) :5165-5181