One-Pot Three-Step Synthesis of Pyrazinothienopyrimidines Using Tandem Aza-Wittig/Electrocyclic Ring Closure

被引：6

作者：

Blanco, Gerardo ^{[1
]}

Fernandez-Mato, Antonio ^{[1
]}

Quintela, Jose M. ^{[1
]}

Peinador, Carlos ^{[1
]}

机构：

[1] Univ A Coruna, Dept Quim Fundamental, Fac Ciencias, La Coruna 15071, Spain

来源：

SYNTHESIS-STUTTGART | 2009年 / 03期

关键词：

heterocycles; Wittig reaction; electrocyclic reactions; phosphazenes; cyclizations; NITRIC-OXIDE; DERIVATIVES; INHIBITORS; IMINOPHOSPHORANES; CHEMISTRY;

D O I：

10.1055/s-0028-1083318

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 pyrazino[3',2':4,5]thieno[3,2-d]pyrimidines following a tandem aza-Wittig/electrocyclic ring closure strategy is described. The one-pot, three-step reaction between 3-amino-2-formylthieno[2,3b]pyrazine, primary amines, dichlorotriphenylphosphine and heterocumulenes, proceeded effectively and the yields of the products were higher than in the stepwise process. The products can also be prepared directly by a one-pot, two-step reaction using the same aldehyde, dichlorotriphenylphosphine and isocyanates. The advantages of the present method are easily accessible starting materials, experimental simplicity of the one-pot procedure, and good yields.

引用

页码：438 / 444

页数：7

共 29 条

[11]

Katritzky A.R.R., 1996, Comprehensive Heterocyclic Chemistry, VII

[12]

Lehn J.-M., 1995, Supramolecular Chemistry-Concepts and Perspectives

[13] Thienopyridines: synthesis, properties, and biological activity [J].

Litvinov, VP ;

Dotsenko, VV ;

Krivokolysko, SG .

RUSSIAN CHEMICAL BULLETIN, 2005, 54 (04) :864-904

[14] IB05204, a dichloropyridodithienotriazine, inhibits angiogenesis in vitro and in vivo [J].

Martinez-Poveda, Beatriz ;

Munoz-Chapuli, Ramon ;

Rodriguez-Nieto, Salvador ;

Quintela, Jose M. ;

Fernandez, Antonio ;

Medina, Miguel-Angel ;

Quesada, Ana R. .

MOLECULAR CANCER THERAPEUTICS, 2007, 6 (10) :2675-2685

[15] A new entry to the preparation of pyrrolo[2,3-b]quinolines by an aza Wittig/electrocyclic ring-closure/nitrene insertion process. [J].

Molina, P ;

Alcantara, J ;

LopezLeonardo, C .

TETRAHEDRON, 1997, 53 (09) :3281-3286

[16]

Molina P, 1999, SYNTHESIS-STUTTGART, P326

[17] FUSED PYRIMIDINES BY A TANDEM AZA-WITTIG ELECTROCYCLIC RING-CLOSURE STRATEGY - SYNTHESIS OF PYRAZOLO[3,4-D]PYRIMIDINE, [1,2,3]TRIAZOLO[4,5-D]PYRIMIDINE, AND THIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES [J].

MOLINA, P ;

ARQUES, A ;

VINADER, MV ;

BECHER, J ;

BRONDUM, K .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4654-4663

[18]

MOLINA P, 1994, SYNTHESIS-STUTTGART, P1197

[19]

OKAWA T, 1994, SYNLETT, P555

[20] The aza-Wittig reaction: an efficient tool for the construction of carbon-nitrogen double bonds [J].

Palacios, Francisco ;

Alonso, Concepcion ;

Aparicio, Dornitila ;

Rubiales, Gloria ;

de los Santos, Jesus M. .

TETRAHEDRON, 2007, 63 (03) :523-575

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