Reissert-reaction

Treatment of quinoline or isoquinoline with acid chloride and KCN gives quinaldic acid, aldehyde, and NH3. 

Name Reactions A Collection of Detailed Mechanisms and Synthetic Applications, DOI 10.1007/978-3-319-03979-4 230, Springer International Publishing Switzerland 2014 

Exanqrle 4, Asymmetric organocatalytic allylic alkylation of Reissert compounds  

(a) Reissert, A. Ber. 1905, 38, 1603-1614. (b) Reissert, A. Ber. 1905, 38, 3415-3435. Carl Arnold Reissert was bom in 1860 in Powayen, Germany. He received his Ph.D. In 1884 at Berlin, where he became an assistant professor. He collaborated with Tiemann. Reissert later joined the faculty at Marburg in 1902. 

Ichikawa, E. Shibasaki, M. Synlett 2005,1491-1508. (Review). 

Name Reactions, 4th ed., DOI 10.1007/978-3-642-01053-8 215, Springer-Verlag Berlin Heidelberg 2009 

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IsothiazoIe-5-carboxyIic acid, 3-methyI-bromination, S, 58 Isothiazolecarboxylic acid chlorides Amdt-Eistert reaction, 6, 157 Reissert reactions, 6, 157 Isothiazolecarboxylic acids esters... 

Scheme 10.85 Al-catalysed Reissert reactions of pyridine derivatives with S/O-ligands.

On the other hand, S/0 ligands have been developed to a much lesser extent, although the high efficiency of BINOL-derived hydroxysulfoxides was demonstrated by Shibasaki s group in 2004 for the Reissert reaction. 

The classic Reissert indole synthesis, involving the reductive cyclization of o-ni-trophenylpyruvic acid, has been used for synthesis of 2-ethoxycarbonyl-4-alkoxymethylindo-les.92 The modified Reissert reaction, involving the reductive cyclization of an o-nitrophenyl acetoaldehyde, has been adapted to solid-phase synthesis.93... 

Sydnonimimes are prepared in a similar way to sydnones (Section 5.03.9.2) but rely on the availability of the appropriate aminonitrile (Scheme 8) <2002CRV1091>. Substituted dihydro- and tetrahydrophthalazine 122 and 124, formed from phthalazine by modification of the Reissert reaction, were converted to the novel sydnonimines 123 and 125 (Equation 22) <1995JHC643>. 

Reformatsky reaction, 1, 1 22, 4 Reimer-Tiemann reaction, 13, 2 28, 1 Reissert reaction, 70, 1 Resolution of alcohols, 2, 9 Retro-Diels-Alder reaction, 52, 1 53, 2 Ritter reaction, 17, 3... 

The Reissert reaction of 3,4-dihydro-p-carboline (213) has also been studied 47,48). It has been shown that 3,4-dihydro-p-carboline (213) afforded 1-cyano-2,9-dibenzoyl-l,2,3,4-tetrahydro-P-carboline (214) with a phase-transfer catalyst and trimethylsilyl cyanide (Scheme 27). However, the normal Reissert product 2-benzoyl-l-cyano-l,2,3,4-tetrahydro-p-carboline (215) was obtained when a catalytic amount of anhydrous aluminum chloride was used in addition to the trimethylsilyl cyanide reagent. Reaction of 214 with sodium... 

The Reissert reaction exemplifies the B pathway (equation 73), and is of course a notable method for aldehyde and alkaloid synthesis. The Fujiwara reaction (81JOC3175), a colour test, provides an example of Type D behavior (Scheme 50). 

The work described in the next section on the family of Reissert reactions might provide a clue to the direction of future work with these interesting phosphorus derivatives of pyridine. The reactions discussed above bear direct comparison with the Reissert-Kaufmann (Scheme 106), Feely-Beavers-Tani (equations 113 and 114) and Reissert (Schemes 107-110) reactions. An analogue of the Reissert-Henze reaction has yet to be reported. 

Reissert Reaction (Grosheintz-Fischer-Reissert Aldehyde Synthesis)... 

In the Reissert reaction, 1-benzoylquinolinium ions (formed in situ from quinolines and PhCOCl) and cyanide ions give Reissert compounds thus, quinoline itself forms (313). These Reissert compounds are hydrolyzed by dilute alkali to, for example, quinoline-2-carboxylic acids and benzaldehyde. Isoquinolines also form Reissert compounds (e.g. 314). 

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