Heterocycles Synthesis at Carbonylation of Acetylenic Compounds

Authors

  • S.A. Vizer Institute of Chemical Sciences MES RK, Sh. Walikhanov str. 106, Almaty, 480100, Kazakhstan
  • K.B. Yerzhanov Institute of Chemical Sciences MES RK, Sh. Walikhanov str. 106, Almaty, 480100, Kazakhstan

DOI:

https://doi.org/10.18321/ectj294

Abstract

The carbonylation of unsaturated hydrocarbons, alcohols, organic halides and other substrates catalyzed by transition metals, salts of transition metals and organometallic complexes is a wide used synthesis method of new carbonyl, carboxyl and alkoxy carbonyl containing compounds including creation or modificationt of heterocycles. The data about synthesis of heterocycles at carbonylation of acetylenic compounds have been appeared at last 20 years and are demonstrated in our review. Introduction of carbon monoxide in the catalytic reactions of acetylenic compounds permits to obtain in oneput process the diverse heterocycles, having carbonyl, carboxyl or alkoxycarbonyl substitutes or containing these fragments inside of heterocycles.

References

(1). Nefyodov B.K. Sintezy organicheskih soedinenij na osnove okisi ugleroda, M.: Nauka, 1978.

(2). Yan Yu.B., Nefyodov B.K. Sintezy na osnove oksidov ugleroda, M.: Himiya, 1987.

(3). Falbe J. New Synthesis with Carbon Monoxide, Berlin: Springer, 1980.

(4). Gulevich Yu.V., Bumagin N.A., Beletskaya I.P. Uspehi himii 57 (4): 529 (1988).

(5). Lapidus A.L., Pirozhkov S.D. Uspehi himii 58 (2): 197 (1989).

(6). Ojima I Chem. Rev. 88 (7): 1011 (1988).

(7). Gauthier-Lafaye J., Perron R., Ind. Appl. Homogeneous Catal.-Dordrecht etc. 19 (1988).

(8). Tanaka M., Kagaku to kogyo (Osaka) Sci. and Ind. 56 (6): 201 (1982).

(9). Chiusoli G.P., Transition Met. Chem. 12 (1) 89 (1987).

(10). Chiusoli G.P., Costa M., Masarati E., Salerno G., J. Organometal Chem. 255 (3): C. 35 (1983).

(11). Chiusoli G.P., Costa M., Pergreffi P., Reverberi S., Salerno G., Gazz. Chim. Ital. 115 (12): 691 (1985).

(12). Chiusoli G.P., Costa M., Reverberi S., Synthesis 4: 262 (1989).

(13). Chiusoli G.P., Costa M., Gerbella M., Salerno G., Gazz. Chim. Ital. 115 (12): 697 (1985).

(14). Chiusoli G.P., Costa M., Reverberi S., Salerno G., Gazz. Chim. Ital. 117: 695 (1987).

(15). Chiusoli G.P., Pallini L., Terenghi M.G., Transition Metal. Chem. 8 (3): 189 (1983).

(16). Abdulganieva S.A., Manchuk Z.N., Zhaparova Z.M., Erzhanov K.B. Zhurn.Org.Khim. 28 (1): 175 (1992).

(17). Vizer S.A., Yerzhanov K.B., Manchuk Z.N., Wieser A.G., Eurasian ChemTech Journal 1 (1): 1 (1999).

(18). Oppolzer W., Bedoya-Zurita M., Switzer C.Y., Tetrahedron Lett. 29 (49): 6433 (1988).

(19). Oppolzer W., Keller T.H., Bedoya-Zurita M., Stone C., Tetrahedron Lett. 30 (43): 5883 (1989).

(20). Kondo Y., Sakamoto T., Yamanaka M., Heterocycles 29 (6): 1013 (1989).

(21). Kondo Y., Shiga F., Murata N., Sakamoto T., Yamanaka H., Tetrahedron 50 (41): 11803 (1994).

(22). Arcadi A., Cacchi S., Carnicelli V., Marinelli F., Tetrahedron 50 (2): 437 (1994).

(23). Okuro K., Furuune M., Miura M., Nomura M., J. Org. Chem. 57 (17): 4754 (1992).

(24). Kalinin V.N., Shostakovsky M.V., Ponomaryov A.B., Doklady Akad. Nauk SSSR, 317 (6): 1395 (1991).

(25). An Z., Catellani M., Chiusoli G.P. – J. Organometal. Chem. 371 (3): C51-C52 (1989).

(26). Kalinin V.N., Shostakovsky M.V., Ponomaryov A.B., Doklady Akad. Nauk SSSR, 312 (5): 1142 (1990).

(27). Kalinin V.N., Shostakovsky M.V., Ponomaryov A.B., Tetrahedron Lett. 31(28): 4073 (1990).

(28). Barberan O., Alami M., Brion J.-D., Tetrahedron Lett. 42: 2657 (2001).

(29). Mizuno T., Nakamura F., Ishino Y., Nishiguchi I., Hirashima T., Ogawa A., Kambe N., Sonoda N., Synthesis (BRD) 10: 770 (1989).

(30). Bonardi A., Costa M., Gabriele B., Salerno G., Chiusoli G.P., Tetrahedron Lett. 36 (41): 7495 (1995).

(31). Bacchi A., Chiusoli G.P., Costa M., Gabriele B., Righi C., Salerno G., J. Chem. Soc. Chem. Commun. (13): 1209 (1997).

(32). Chiusoli G.P., Costa M., Gabriele B., Salerno G., J. Mol. Catal. A. 143 (1-3): 297 (1999).

(33). Kupchan S.M., Eakin M.A., Thomas A.M., J. Med. Chem. 14 (12): 1147 (1971).

(34). Mc Phail A.T., Onan K.D., Lee K.-H., Ibuka T., Kozuka M., Shingu T., Huang H.-C., Tetrahedron Lett. (32): 2739 (1974).

(35). Jones E.R.H., Shen T.Y., Whiting M.C., J. Chem. Soc. 230 (1950).

(36). Norton J.R., Shenton K.E., Schwartz J., Tetrahedron Lett. 51 (1975).

(37). Murray T.F., Samsel E.G., Varma V., Norton J.R., J. Am. Chem. Soc. 103 (25): 7520 (1981).

(38). Murray T.F., Norton J.R., J. Am. Chem. Soc. 101: 4107 (1979).

(39). Gabriele B., Salerno G., De Pascali F., Costa M., Chiusoli G.P. J. Chem. Soc., Perkin trans. 1, (2): 147 (1997).

(40). Gabriele B., Costa M., Salerno G., Chiusoli G.P., J. Chem. Soc., Chem. Commun., (12): 1429 (1994).

(41). Tamaru Y., Hojo M. and Yoshida Z.-i., J. Org. Chem., 56(3): 1099 (1991).

(42). Matsuda I., Ogiso A., Sato S., J. Am. Chem. Soc., 112(16): 6120 (1990).

(43). Inoue Y., Ohuchi K., Yen I.F., Imaizumi S., Bull. Chem. Soc. Jpn. 62 (11): 3518 (1989).

(44). Hong P., Mise T., Yamazaki H., Chem. Lett. (7): 989 (1981).

(45). Mise T., Hong P., Yamazaki H., Chem. Lett. 993 (1981).

(46). Ko K., Mice T., Yamazaki H., Applic. Jp. N59-164787. Appl. 9.03.83 N58-38428, publ. 17.09.84. C 07 D 307158 [RZhKhim, 19 N 73 P (1985)].

(47). Doyama K., Joh T., Onitzuka K., Shiohara T., Takahashi S., J. Chem. Soc., Chem. Commun. 649 (1987).

(48). Joh T., Doyama K., Onitzuka K., Shihara T., Takahashi S., Organometallics, 10(7): 2493 (1991).

(49). Gusev B.P., Alperina E.A., Kutcherov V.F., Pirozhkov S.D., Lapidus A.L., Izvestija AN SSSR, ser. Khim. (3): 603 (1980).

(50). Alper H., Currie J.K., Des Abbayes H, J. Chem. Soc. Chem. Commun. 311 (1978).

(51). Alper H., Petrignani J.F., J. Chem. Soc. Chem. Commun. 1154 (1983).

(52). Arzoumanian H., Petrignani J.F., Tetrahedron Lett. 27(49): 5979(1986).

(53). Sauer J.C., Cramer R.D., Engelhardt V.A., Ford T.A., Holmquist H.E., Howk B.W., J. Am. Chem. Soc. 81(14): 3677 (1959).

(54). Albanesi G., Tovaglieri M., Chim. Ind. (Milan) 41: 189 (1959).

(55). Albanesi G., Chim. Ind. (Milan) 46 (10): 1169 (1964).

(56). Albanesi G., Farina R., Taccioli A., Chim. Ind. (Milan) 48 (11): 1151 (1966).

(57). Varadi G., Horvath I.T., Palagyi J., Bak T., Palyi G., J. Mol. Catal. 9: 457 (1980).

(58). Guthrie D.J.S., Khand I.U., Knox G.R., Kollmeier J., Pauson P.L., J. Organomet. Chem. 90: 93 (1975).

(59). Palyi G., Varadi G., Horvath I.T., J. Mol. Catal. 13 (1): 61 (1981).

(60). Rautenstrauch V., Megard P., Gamper B., Bourdin B., Walther E., Bernardinelli G., Helv. Chim. Acta 72: 811 (1989).

(61). Wang J.-X., Alper H., J. Org. Chem., 51(2): 273 (1986).

(62). Nogi T., Tsuji J., Tetrahedron, 25 (17): 4099 (1969).

(63). Sakurai Y., Sakaguchi S., Ishii Y., Tetrahedron Lett. 40 (9): 1701 (1999).

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Published

2003-04-15

How to Cite

Vizer, S., & Yerzhanov, K. (2003). Heterocycles Synthesis at Carbonylation of Acetylenic Compounds. Eurasian Chemico-Technological Journal, 5(2), 145–160. https://doi.org/10.18321/ectj294

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