Synthesis of novel 5-phenylimidazo[1,2-c]quinazolin-3-amine derivatives via Groebke-Blackburn-Bienaym, multicomponent reaction

被引：17

作者：

Akbarzadeh, Tahmineh ^{[1
]}

Ebrahimi, Abolfath ^{[1
]}

Saeedi, Mina ^{[2
]}

Mahdavi, Mohammad ^{[2
]}

Foroumadi, Alireza ^{[2
]}

Shafiee, Abbas ^{[2
]}

机构：

[1] Univ Tehran Med Sci, Dept Med Chem, Fac Pharm, Tehran 14176, Iran

[2] Univ Tehran Med Sci, Dept Med Chem, Pharmaceut Sci Res Ctr, Fac Pharm, Tehran 14176, Iran

来源：

MONATSHEFTE FUR CHEMIE | 2014年 / 145卷 / 09期

关键词：

Groebke-Blackburn-Bienayme; Isocyanides; Multicomponent reactions; Phenylimidazo[1,2-c] quinazolines; 3-COMPONENT REACTION; ONE-POT; CHLORIDE; 4-COMPONENT; CATALYST; ACID;

D O I：

10.1007/s00706-014-1204-y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed an efficient and environmentally benign one-pot procedure for synthesis of novel N-alkyl-2-aryl-5-phenylimidazo[1,2-c]quinazolin-3-amine derivatives by use of the Groebke-Blackburn-Bienaym, multicomponent reaction. The title compounds were synthesized in good yields from 2-phenylquinazolin-4-amine, aromatic aldehydes, and isocyanides in the presence of ammonium chloride under solvent-free conditions.

引用

页码：1483 / 1487

页数：5

共 25 条

[1] Catalyst-free three-component reaction between 2-aminopyridines (or 2-aminothiazoles), aldehydes, and isocyanides in water [J].

Adib, Mehdi ;

Mahdavi, Mohammad ;

Noghani, Mahsa Alizadeh ;

Mirzaei, Peiman .

TETRAHEDRON LETTERS, 2007, 48 (41) :7263-7265

[2]

Bienaymé H, 1998, ANGEW CHEM INT EDIT, V37, P2234, DOI 10.1002/(SICI)1521-3773(19980904)37:16<2234::AID-ANIE2234>3.0.CO

[3]

2-R

[4] Parallel synthesis of 3-aminoimidazo[1,2-a]pyridines and pyrazines by a new three-component condensation [J].

Blackburn, C ;

Guan, B ;

Fleming, P ;

Shiosaki, K ;

Tsai, S .

TETRAHEDRON LETTERS, 1998, 39 (22) :3635-3638

[5] Exploiting the dual reactivity of o-isocyanobenzamide:: Three-component synthesis of 4-imino-4H-3,1-benzoxazines [J].

Bonne, D ;

Dekhane, M ;

Zhu, JP .

ORGANIC LETTERS, 2005, 7 (23) :5285-5288

[6] Ammonium chloride promoted Ugi four-component, five-center reaction of α-substituted α-isocyano acetic acid:: A strong solvent effect [J].

Bonne, D ;

Dekhane, M ;

Zhu, JP .

ORGANIC LETTERS, 2004, 6 (25) :4771-4774

[7]

Bourguignon JJ, 1992, US Patent, Patent No. [5,128,338, 5128338]

[8]

CARDELLINI M, 1975, FARMACO-ED SCI, V30, P536

[9] Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility [J].

Cave, GWV ;

Raston, CL ;

Scott, JL .

CHEMICAL COMMUNICATIONS, 2001, (21) :2159-2169

[10]

Chern JW, 1996, US Patent, Patent No. [5,512,677, 5512677]

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