Synthesis of 1,1-diamino-2-thioacylethylenes: A novel C-thioacylation by the Willgerodt-Kindler reaction

Rajappa, S.; Nair, M. D.; Sreenivasan, R.; Advani, B. G.

doi:10.1016/0040-4020(82)80145-2

Cited by 43 publications

(4 citation statements)

References 8 publications

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“…47 In 1982, the C-thioacylation of pyrimidines using aldehydes employing the Willgerodt-Kindler reaction was reported by Rajappa and co-workers. 48 During this investigation it was observed that the use of salicaldehydes led to the formation of novel betaine heterocycles as by-products (Scheme 23). The structure of these fascinating compounds was subsequently confirmed by X-ray crystallography.…”

Section: Heterocycle Synthesismentioning

confidence: 99%

“…To this end, this reaction protocol has been utilised in numerous synthetic applications where these functionalities are required including in the preparation of pharmaceutically relevant compounds. 17,28,43,48,56 The Willgerodt-Kindler reaction has also been employed in the preparation of key intermediates in the total syntheses of natural products including the biologically important polyphenolic stilbene, resveratrol. 57 Kanbara and co-workers have reported the synthesis of polythioamides through the polymerisation of dialdehydes with diamine monomers in the presence of sulfur.…”

Section: Other Applications Of the Willgerodt-kindler Reactionmentioning

confidence: 99%

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Recent advances in the Willgerodt–Kindler reaction

2013

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The Willgerodt-Kindler reaction has, in recent years, received limited attention and application in synthetic organic chemistry. With the advent of new technology such as microwave-assisted heating, several new, high-yielding, practical, and more environmentally friendly reaction protocols have been developed. This review aims to once again draw attention to this relatively underutilised process by highlighting the recent developments in the Willgerodt-Kindler reaction in the synthesis of (thio)amides, carboxylic acids, and heterocycles.

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Section: Heterocycle Synthesismentioning

confidence: 99%

Section: Other Applications Of the Willgerodt-kindler Reactionmentioning

confidence: 99%

Recent advances in the Willgerodt–Kindler reaction

2013

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“…94 ± 99 Cyanoacetic acid in the presence of Ac 2 O, 94 acetic anhydride, 95 isocyanates, isothiocyanates, 96,97 and benzoylisothiocyanate were used as acylating agents. 98,99 Scheme 1…”

Section: Synthesis Based On Various S- N-and C-cyano Derivativesmentioning

confidence: 99%

Synthesis and properties of β,β-bisfunctionalised keteneN,N-acetals

Makarov¹,

Граник²

1998

Russ. Chem. Rev.

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We make a systematic investigation of stationary cylindrically symmetric solutions to the five-dimensional Einstein and Einstein-Gauss-Bonnet equations. Apart from the fivedimensional neutral cosmic string metric, we find two new exact solutions which qualify as cosmic strings, one corresponding to an electrically charged cosmic string, the other to an extended superconducting cosmic string surrounding a charged core. In both cases, test particles are deflected away from the singular line source. We extend both kinds of solution to exact multi-cosmic-string solutions.

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“…The synthesis of ketoketen [8] or cyanoketene S,Sacetals [9] as well as heterocyclic ketene N,N- [10][11][12][13][14][15] or N,S-acetals [16][17][18] has attracted considerable attention as these compounds have been used as versatile starting materials for the synthesis of a wide variety of fused heterocycles. In an extension of our studies [19][20][21][22] on the application of cyanoketen, ketoketene, cyanoketoketene S,S-or N,S-acetals in heterocyclic synthesis, we report here the synthesis of some new spiro naphtho [2,3-d] [1,3]dithiole-4,9-diones using hetero cyclic ketene S,S-acetals 1.…”

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confidence: 99%