Synlett 2016; 27(05): 782-788
DOI: 10.1055/s-0035-1560383
letter
© Georg Thieme Verlag Stuttgart · New York

Unusual Acid- and Base-Catalyzed C–N Bond Formation Approach through Reaction of Chromonyl Meldrum’s Acid and Nitrogen Binucleophiles

Saeed Balalaie*
a   Peptide Chemistry Research Center, K. N. Toosi University of Technology, P.O. Box 15875-4416 Tehran, Iran   Email: balalaie@kntu.ac.ir
b   Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran
,
Hamid Reza Bijanzadeh
a   Peptide Chemistry Research Center, K. N. Toosi University of Technology, P.O. Box 15875-4416 Tehran, Iran   Email: balalaie@kntu.ac.ir
,
Saber Mehrparvar
a   Peptide Chemistry Research Center, K. N. Toosi University of Technology, P.O. Box 15875-4416 Tehran, Iran   Email: balalaie@kntu.ac.ir
,
Frank Rominger
c   Organisch-Chemisches Institut der Universitaet Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
› Author Affiliations
Further Information

Publication History

Received: 22 August 2015

Accepted after revision: 20 October 2015

Publication Date:
30 November 2015 (online)


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Abstract

Reaction of chromonyl Meldrum’s acid and N-substituted 2-aminobenzamides was studied in the presence of acidic and basic catalysts. The use of methanesulfonic acid as a catalyst in this reaction led to the synthesis of chromonyl quinazolinones through employing Meldrum’s acid as a carbon leaving group. However, in the presence of basic catalyst, this reaction gave functionalized 2-pyridones.

Supporting Information