40740-39-4Relevant academic research and scientific papers
Design, Sustainable Synthesis, and Programmed Reactions of Templated N-Heteroaryl-Fused Vinyl Sultams
Laha, Joydev K.,Sharma, Shubhra,Kirar, Seema,Banerjee, Uttam C.
, p. 9350 - 9359 (2017/09/23)
A de novo design and synthesis of N-heteroaryl-fused vinyl sultams as templates for programming chemical reactions on vinyl sultam periphery or (hetero)aryl ring is described. The key features include rational designing and sustainable synthesis of the template, customized reactions of vinyl sultams at C=C bond or involving N-S bond cleavage, and reactions on the periphery of the heteroaryl ring for late-stage diversification. The simple, easy access to the template coupled with opportunities for the synthesis of diversely functionalized heterocyles from a single template constitutes a rare study in contemporary organic synthesis.
PYRROLE CHEMISTRY. XXIV. THE VILSMEIER FORMYLATION AND CYANATION OF PYRROLE ACETALS. A SYNTHESIS OF PYRROLE-2,3,5-TRICARBOXALDEHYDE
Loader, Charles E.,Barnett, Graham H.,Anderson, Hugh J.
, p. 383 - 389 (2007/10/02)
The preparation of the acetals of a number of pyrrole mono- and dicarboxaldehydes is described.It is shown that, provided the reactivity of the unsubstituted ring positions on the pyrrole nucleus is not too low, a carboxaldehyde or a carbonitrile group may be substituted on the pyrrole ring using the Vilsmeier reaction or chlorosulfonyl isocyanate respectively. Vilsmeier formylation of the diacetal, 2,4-di(5,5-dimethyl-1,3-dioxan-2-yl)-pyrrole, followed by hydrolysis gave pyrrole-2,3,5-tricarboxaldehyde.
Pyrrole chemistry. XXIII. The cyanation of substituted pyrroles with chlorosulfonyl isocyanate (CSI). New syntheses of pyrrole-3-carbonitriles
Loader, Charles E.,Anderson, Hugh J.
, p. 2673 - 2676 (2007/10/02)
Chlorosulfonyl isocyanate (CSI) reacts not only with pyrrole itself but with pyrroles having powerful electron-withdrawing groups in the 2-position.Suitable choice of electron-withdrawing groups allows selective 4-substitution of the pyrrole ring.The N-chlorosulfonyl amides formed are readily converted to the corresponding nitriles.The procedure has been used to provide syntheses of pyrrole-3-carbonitrile and its 1-methyl homologue.
Pyrrole chemistry. XXI. Synthetic approaches to cyanopyrroles
Barnett, Graham H.,Anderson, Hugh J.,Loader, Charles, E.
, p. 409 - 411 (2007/10/02)
The Vilsmeier-Haack reaction with pyrrole and 1-methylpyrrole has been modified to provide a direct synthesis of the corresponding 2-nitriles.Chlorosulfonyl isocyanate may be used to prepare the some compounds, but less satisfactorily.The latter reagent does enable the synthesis of pyrrole-2,4-dicarbonitrile in one step.The dinitrile may be reduced to pyrrole-2,4-dicarboxaldehyde.
