A Clean and One-Pot Synthesis of Spiroindoline-Pyranopyrazoles

被引:48
作者
Ahadi, Somayeh [1 ]
Yasaei, Zahra [1 ]
Bazgir, Ayoob [1 ]
机构
[1] Shahid Beheshti Univ, Dept Chem, Tehran 1983963113, Iran
关键词
MULTICOMPONENT REACTIONS; EFFICIENT SYNTHESIS; SPIRO-HETEROCYCLES; 3-COMPONENT; SPIROOXINDOLES; DERIVATIVES; FLUORINE; FACILE;
D O I
10.1002/jhet.437
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
Piperidine catalyzes efficiently the one-pot, four-component reaction of beta-ketoesters, hydrazine hydrate, malononitrile, and isatines in aqueous media. The reaction was done at room temperature and the spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitriles were obtained with high yields and purity via an easy work-up procedure. These compounds were also investigated in vitro for antibacterial activities.
引用
收藏
页码:1090 / 1094
页数:5
相关论文
共 36 条
[1]
Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents [J].
Abdel-Rahman, AH ;
Keshk, EM ;
Hanna, MA ;
El-Bady, SM .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) :2483-2488
[2]
Synthesis and biological evaluation of some new coumarin derivatives [J].
Al-Haiza, MA ;
Mostafa, MS ;
El-Kady, MY .
MOLECULES, 2003, 8 (02) :275-286
[3]
An efficient synthesis of spiro[dibenzo[b,i]xanthene-13,3′-indoline]-pentaones and 5H-dibenzo[b,i]xanthene-tetraones [J].
Bazgir, Ayoob ;
Tisseh, Zeinab Noroozi ;
Mirzaei, Peiman .
TETRAHEDRON LETTERS, 2008, 49 (35) :5165-5168
[4]
One-pot synthesis and antibacterial activities of pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-dione derivatives [J].
Bazgir, Ayoob ;
Khanaposhtani, Maryam Mohammadi ;
Soorki, Ali Abolhasani .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (21) :5800-5803
[5]
A novel three-component method for the synthesis of triazolo[1,2-a]indazole-triones [J].
Bazgir, Ayoob ;
Seyyedhamzeh, Mozhdeh ;
Yasaei, Zahra ;
Mirzaei, Peiman .
TETRAHEDRON LETTERS, 2007, 48 (50) :8790-8794
[6]
A novel reaction of 6-amino-uracils and isatins [J].
Dabiri, Minoo ;
Azimi, Seyyedeh Cobra ;
Khavasi, Hamid Reza ;
Bazgir, Ayoob .
TETRAHEDRON, 2008, 64 (30-31) :7307-7311
[7]
Dabiri M, 2008, HETEROCYCLES, V75, P87
[8]
Facile three-components, one-pot synthesis of pyrimido[4,5-d]pyrimidine-2,5-dione derivatives under microwave-assisted conditions [J].
Dabiri, Minoo ;
Arvin-Nezhad, Hamid ;
Khavasi, Hamid R. ;
Bazgir, Ayoob .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (05) :1009-1011
[9]
A novel and efficient synthesis of pyrimido[4,5-d]pyrimidine-2,4,7-trione and pyrido[2,3-d:6,5-d] dipyrimidine-2,4,6,8-tetrone derivatives [J].
Dabiri, Minoo ;
Arvin-Nezhad, Harnid ;
Khavasi, Hamid Reza ;
Bazgir, Ayoob .
TETRAHEDRON, 2007, 63 (08) :1770-1774
[10]
A novel three-component, one-pot synthesis of 1,2-dihydro-1-arylnaphtho [1,2-e][1,3]oxazine-3-one derivatives under microwave-assisted and thermal solvent-free conditions [J].
Dabiri, Minoo ;
Delbari, Akram Sadat ;
Bazgir, Ayoob .
SYNLETT, 2007, (05) :821-823