Phospho sulfonic acid: a novel and efficient solid acid catalyst for the one-pot preparation of indazolo[1,2-b]-phthalazinetriones

被引：48

作者：

Kiasat, Ali Reza ^{[1
]}

Mouradzadegun, Arash ^{[1
]}

Saghanezhad, Seyyed Jafar ^{[1
]}

机构：

[1] Shahid Chamran Univ, Coll Sci, Dept Chem, Ahvaz 6135743169, Iran

来源：

JOURNAL OF THE SERBIAN CHEMICAL SOCIETY | 2013年 / 78卷 / 04期

关键词：

indazolo[1,2-b]phthalazinetrione; multicomponent reaction; phthalhydrazide; dimedone; solvent-free; phospho sulfonic acid; DERIVATIVES;

D O I：

10.2298/JSC120508088K

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient one-pot condensation of aldehyde, dimedone and phthalhydrazide has been achieved in the presence of a catalytic amount of phospho sulfonic acid as a novel environmentally benign heterogeneous solid acid under solvent-free conditions. Diverse indazolo[1,2-b]phthalazinetrione derivatives were prepared in good to excellent yields in short times. The economical factors (time, cost, waste, etc.) for this three-component reaction hold promise for the future of organic synthesis.

引用

页码：469 / 476

页数：8

共 27 条

[1]

Al'-Assar F., 2002, PHARM CHEM J+, V36, P598, DOI [DOI 10.1023/A:1022665331722, 10.1023/a:1022665331722]

[2] 3-phenyl-6-(2-pyridyl)methyloxy-1,2,4-triazolo[3,4-α]phthalazines and analogues:: High-affinity γ-aminobutyric acid-A benzodiazepine receptor ligands with α2, α3, and α5-subtype binding selectivity over α1 [J].

Carling, RW ;

Moore, KW ;

Street, LJ ;

Wild, D ;

Isted, C ;

Leeson, PD ;

Thomas, S ;

O'Connor, D ;

McKernan, RM ;

Quirk, K ;

Cook, SM ;

Atack, JR ;

Wafford, KA ;

Thompson, SA ;

Dawson, GR ;

Ferris, P ;

Castro, JL .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (07) :1807-1822

[3]

El-Sakka SS, 2009, AFINIDAD, V66, P167

[4] One-pot synthesis of aliphatic and aromatic 2H-indazolo[2,1-b]phthalazine-triones catalyzed by N-halosulfonamides under solvent-free conditions [J].

Ghorbani-Vaghei, Ramin ;

Karimi-Nami, Rahman ;

Toghraei-Semiromi, Zahra ;

Amiri, Mostafa ;

Ghavidel, Mehdi .

TETRAHEDRON, 2011, 67 (10) :1930-1937

[5] One-Pot and Efficient Synthesis of Triazolo[1,2-a]indazole-triones via Reaction of Arylaldehydes with Urazole and Dimedone Catalyzed by Silica Nanoparticles Prepared from Rice Husk [J].

Hamidian, Hooshang ;

Fozooni, Samieh ;

Hassankhani, Asadollah ;

Mohammadi, Sayed Zia .

MOLECULES, 2011, 16 (11) :9041-9048

[6] Highly efficient synthesis of triazolo[1,2-a]indazole-triones and novel spiro triazolo[1,2-a]indazole-tetraones under solvent-free conditions [J].

Hasaninejad, Alireza ;

Zare, Abdolkarim ;

Shekouhy, Mohsen .

TETRAHEDRON, 2011, 67 (02) :390-400

[7] Structural variations in keto-glutamines for improved inhibition against hepatitis A virus 3C proteinase [J].

Jain, RP ;

Vederas, JC .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (14) :3655-3658

[8] Efficient one-pot syntheses of 2H-indazolo[2,1-b] phthalazine-triones by catalytic H2SO4 in water-ethanol or ionic liquid [J].

Khurana, Jitender M. ;

Magoo, Devanshi .

TETRAHEDRON LETTERS, 2009, 50 (52) :7300-7303

[9] Synthesis of 1-/2-substituted-[1,2,3]triazolo[4,5-g]phthalazine4,9-diones and evaluation of their cytotoxicity and topoisomerase II inhibition [J].

Kim, Jin Sung ;

Rhee, Hee-Kyung ;

Park, Hyen Joo ;

Lee, Sang Kook ;

Lee, Chong-Ock ;

Choo, Hea-Young Park .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (08) :4545-4550

[10] Synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction using organocatalysts [J].

Kumar, Atul ;

Maurya, Ram Awatar .

TETRAHEDRON, 2007, 63 (09) :1946-1952

← 1 2 3 →