Dipropargyl 2,2-isophthaloylbis(hydrazinecarboxylate).docVIP

Molbank 2010, M701; doi:10.3390/M701 OPEN ACCESS molbank ISSN 1422-8599 /journal/molbank Short Note Dipropargyl 2,2-isophthaloylbis(hydrazinecarboxylate) Thimo Huber 1 and David D. Díaz 1,2,* 1 Institut für Organische Chemie, Universit?t Regensburg, Universit?tsstr. 31, 93040 Regensburg, Germany 2 ICMA, CSIC-Universidad de Zaragoza, Pedro Cerbuna 12, 50009 Zaragoza, Spain * Author to whom correspondence should be addressed; E-Mail: David.Diaz@chemie.uni-regensburg.de Received: 7 September 2010 / Accepted: 22 October 2010 / Published: 25 October 2010 Abstract: The synthesis of dipropargyl 2,2-isophthaloylbis(hydrazinecarboxylate) (3) by an addition-elimination reaction between isophthalic dihydrazide (1) and dipropargyl dicarbonate (2) is reported. The title compound was characterized by FT-IR, 1H NMR, 13C NMR, EI-MS, elemental analysis and melting point determination. Keywords: dicarbonate; alkyne; hydrazide; addition-elimination reaction Substituted hydrazides have found important applications as traceless linkers for solid-phase synthesis [1] or as synthetic intermediates for the synthesis of pesticides [2], steroids [3], and antimycobacterials [4]. Taking advantage of their donor/acceptor hydrogen-bonding ability, hydrazides have been also used in the formation of molecular duplex strands via interstrand hydrogen bonds [5]. On the other hand, terminal alkynes are versatile functional groups in organic synthesis and materials science mainly due to their characteristic metal-catalyzed reactions [6]. In particular, polyvalent alkynes have emerged as valuable cross-linking agents and monomers in the renowned ‘click’ chemistry [7], with special emphasis on materials science [8,9]. Herein, we report the synthesis of dipropargyl 2,2-isophthaloylbis(hydrazinecarboxylate) (3) by an addition-elimination reaction between isophthalic dihydrazide (1) and dipropargyl dicarbonate (2) i