Reaction of (Alkylthio)chloroacetylenes with Thiosemicarbazones: A Route to Functionalized Thiazoles

Svetlana G. D’yachkova; Elena A. Nikitina; Ludmila I. Larina; Peter E. Ushakov; Nina K. Gusarova; Lidiya M. Sinegovskaya; Boris A. Trofimov

doi:10.1055/s-2002-28518

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Reaction of (Alkylthio)chloroacetylenes with Thiosemicarbazones: A Route to Functionalized Thiazoles

Svetlana G. D’yachkova*, Elena A. Nikitina, Ludmila I. Larina, Peter E. Ushakov, Nina K. Gusarova, Lidiya M. Sinegovskaya, Boris A. Trofimov
A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia
Fax: +7(395)2396046; e-Mail: dsg@irioch.irk.ru;

Abstract

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Abstract

(Alkylthio)chloroacetylenes 1 react with thiosemicarbazones 2 at room temperature in a medium of aliphatic ketone to form hydrochlorides of 2-alkanone-N-[4-(organylthio)-1,3-thiazol-2-yl]hydrazones 3 in yields of up to 65%.

Key words

(alkylthio)chloroacetylenes - thiosemicarbazones - hydrochlorides of 2-alkanone-N-[4-(organylthio)-1,3-thiazol-2-yl]hydrazones - 2-alkanon-N-[4-(organylthio)-1,3-thiazol-2-yl]hydra-zones - synthesis

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References

1 Mirskova AN. Seredkina SG. Kalikhman ID. Voronkov MG. Izv. Akad. Nauk Ser. Khim. 1988, N3: 616 ; Chem. Abstr. 1988, 109, 210488k

2a D’yachkova SG. Gusarova NK. Nikitina EA. Larina LI. Sinegovskaya LM. Abramov AV. Trofimov BA. Zh. Obshch. Khim. 2001, 71: 1816

2b D’yachkova SG. Gusarova NK. Beskrylaya EA. Larina LI. Trofimov BA. Russ. Chem. Bull. 2000, 49: 1319

3 Nakhmanovich AS. Glotova TE. Komarova TN. Sigalov MV. Romanenko LS. Khim. Geterotsikl. Soedin. 1990, N10: 1421

4 Gordon AJ. Ford PA. In The Chemist’s Companion A Handbook of Practical Data Techniques and References A Wiley-Interscience Publication, John Wiley & Sons; New York: 1972.

5 Bellamy LJ. In The Infra-Red Spectra of Complex Molecules Methuen & Co. Ltd, John Wiley & Sons; London: 1957.

6 Physical methods in heterocyclic chemistry Katritzky AR. Academic Press; New York: 1963.

7 Bol’shakov GF. Vatago VC. Agrest FB. Ultrafioletovye spektry geterotsiklicheskikh soedineniy Khimiy; Leningrad: 1969. ; in Russian

8 Stern ES. Timmons CJ. In Electronic Absorption Spectroscopy in Organic Chemistry Edward Arnold Ltd; London: 1970.

9 Rabiller C. Renou JP. Martin GJ. J. Chem. Soc., Perkin Trans. 2 1977, 5: 536

10 Eun-Jeong S. Kye-Young K. Sueg-Geun L. Bull. Korean Chem. Soc. 1994, 15: 911

11 Krivdin LB. Zinchenko SV. Sherbakov VV. Kalabin GA. Contreras RH. Tufro MF. Ruiz de Azua MC. Giribet CG. Magn. Reson. Chem. 1989, 84: 1

12 Krivdin LB. Kalabin GA. Prog. Nucl. Magn. Reson. Spectrosc. 1989, 21: 293

13 Witanowski M. Stefaniak L. Webb GA. In Annual Reports on NMR Spectroscopy Vol. 11B Nitrogen NMR Spectroscopy: Webb GA. Academic Press; London: 1981. p.502

14 Larina LI. Karnaukhova RV. Nachmanovich VA. Shagun AS. Ushakov PE. Lopyrev VA. J. Molec. Structure 2002, 604: 165

15 Levy GC. Nelson GL. Carbon-13 Nuclear Magnetic Resonance for Organic Chemists John Wiley & Sons; New York: 1972.

16 Breitmaier E. Voelter W. ¹³ C spectroscopy. Methods and Applications in Organic Chemistry Verlag Chemie; New York: 1978.

17 D’yachkova SG. Afonin AV. Kalinina NA. Beskrylaya EA. Mal’kina AG. Kositsina EI. Trofimov BA. Sulfur Lett. 1999, 22: 57

18 Comprehensive Organic Chemistry Vol. 4: Barton D. Ollis WD. Pergamon Press; New York: 1979.

19 Haake P. Bausher LP. McNeal JP. J. Am. Chem. Soc. 1971, 93: 7045

20 Wilson CO. Gisvold O. Doerge RF. Textbook of Medicinal and Pharmaceutical Chemistry Pitman; London: 1966.

21a Organisch-chemische experimentierkunst Johann Ambrosius Barth Verlag; Leipzig: 1962.

21b Comprehensive Organic Chemistry Vol. 3: Barton D. Ollis WD. Pergamon Press; New York: 1979.