A Novel Four-Component Reaction for the Synthesis of 2,5-Diaminofuran Derivatives

Abdolali Alizadeh; Sadegh Rostamnia; Mao-Lin Hu

doi:10.1055/s-2006-941581

LETTER

A Novel Four-Component Reaction for the Synthesis of 2,5-Diaminofuran Derivatives

Abdolali Alizadeh*^a, Sadegh Rostamnia^a, Mao-Lin Hu^b
^a Department of Chemistry, Tarbiat Modarres University, P.O. Box 14115-175, Tehran, Iran
Fax: +98(21)88006544; e-Mail: aalizadeh@modares.ac.ir;
^b School of Chemistry and Materials Science, Wenzhou University, Wenzhou 325027, P. R. of China

Abstract

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Abstract

A facile synthesis of highly functionalized 2,5-diaminofuran derivatives by the multicomponent reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-phenylacetic acid or 2,2-diphenylacetic acid is described.

Key words

alkyl isocyanide - dialkyl acetylenedicarboxylate - aliphatic carboxylic acid - multicomponent reaction

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References

References and Notes

1 Trost BM. Science 1991, 254: 1471

2 Tietze LF. Chem. Rev. 1996, 96: 115

3 Lipshutz BH. Chem. Rev. 1986, 86: 795

4 Nakanishi K. Natural Products Chemistry Kodansha; Tokyo: 1974.

5 Yavari I. Alizadeh A. Anary-Abbasinejad M. Bijanzadeh HR. Tetrahedron 2003, 59: 6083

6 Yavari I. Anary-Abbasinejad M. Alizadeh A. Hossaini Z. Tetrahedron 2003, 59: 1289

7 Yavari I. Anary-Abbasinejad M. Alizadeh A. Monatsh. Chem. 2002, 133: 1221

8 Yavari I. Esmaili AA. Asghari S. Bijanzadeh HR. J. Chem. Res., Synop. 1999, 368

9 Yavari I. Hazeri N. Maghsoodlou MT. Zabarjad-Shiraz N. Monatsh. Chem. 2001, 132: 683

10

Single crystal X-ray structure data for 3f have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 297317.

11 Ugi I. Isonitrile Chemistry Academic; London: 1971.

12 Ugi I. Angew. Chem., Int. Ed. Engl. 1982, 21: 810

13 Dömling A. Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3168

14 Nair V. Viond AU. Nair JS. Sreekanth AR. Rath NP. Tetrahedron Lett. 2000, 41: 6675

15 Walborsky HM. Presiasamy MP. In The Chemistry of Functional Groups Suppl. C: Patai S. Rappaport Z. Wiley; New York: 1983. Chap. 20. p.835

16 Marcaccini S. Torroba T. Org. Prep. Proced. Int. 1993, 25: 141

17 Passerini M. Ragni G. Gazz. Chim. Ital. 1931, 61: 964

18a Dömling A. Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3169

18b Ugi I. J. Prakt. Chem. 1997, 339: 499

18c Ugi I. Steinbrückner C. Chem. Ber. 1961, 94: 734

18d Ugi I. Steinbrückner C. Chem. Ber. 1959, 71: 386

18e Ugi I. Rosendahl K. Chem. Ber. 1961, 94: 2233