Abstract:
Addition reactions of acetyl and benzoyl chlorides to 1-pyrazolines containing a spiro cyclopropane fragment at the adjacent azo group lead selectively and in high yields to the corresponding 1-acyl-3-(chloroethyl)-2-pyrazolines, resulting in opening of the three-membered ring.
Document Type:
Article
Language: English
Citation:
Yu. V. Tomilov, G. P. Okonnishnikova, E. V. Shulishov, O. M. Nefedov, “Electrophilic 1,5-Addition of Acyl Chlorides to Conjugated Azocyclopropanes”, Mendeleev Commun., 4:4 (1994), 119–120
Linking options:
https://www.mathnet.ru/eng/mendc5178
https://www.mathnet.ru/eng/mendc/v4/i4/p119
This publication is cited in the following 11 articles:
D. A. Denisov, D. D. Borisov, K. V. Potapov, R. A. Novikov, Yu. V. Tomilov, “4-Phenylspiro[2.2]pentane-1,1-dicarboxylate: synthesis and reactions with EtAlCl2 and 4,5-diazaspiro[2.4]hept-4-ene derivative”, Mendeleev Commun., 29:4 (2019), 417–418
Roman A. Novikov, Denis D. Borisov, Maria A. Zotova, Dmitry A. Denisov, Yaroslav V. Tkachev, Victor A. Korolev, Evgeny V. Shulishov, Yury V. Tomilov, “Cascade Cleavage of Three-Membered Rings in the Reaction of D–A Cyclopropanes with 4,5-Diazaspiro[2.4]hept-4-enes: A Route to Highly Functionalized Pyrazolines”, J. Org. Chem., 83:15 (2018), 7836
Valentin A. Rassadin, Yvan Six, “Ring-opening, cycloaddition and rearrangement reactions of nitrogen-substituted cyclopropane derivatives”, Tetrahedron, 72:32 (2016), 4701
Ivan P. Klimenko, Andrey F. Medvedev, Victor A. Korolev, G.D. Kolomnikova, Yury V. Tomilov, Yuri N. Bubnov, “First allylboration of organic compounds with the NN double bond. Synthesis of N-allylpyrazolidines and allyl-1,2-diphenylhydrazine”, Journal of Organometallic Chemistry, 694:13 (2009), 2106
E. V. Guseva, Yu. V. Tomilov, “Acylation of fluorine-containing spiro[cyclopropane-1-pyrazolines] and dehydrohalogenation of the resulting adducts”, Russ Chem Bull, 54:2 (2005), 428
Ekaterina V. Guseva, Nikolay V. Volchkov, Yury V. Tomilov, Boris B. Averkiev, Oleg M. Nefedov, “Formation of Cyclobutylidenepyrazolines by Methanolysis of 6‐(2,3,3‐Trifluorocyclobutenyl)‐4,5‐diazaspiro[2.4]hept‐4‐ene”, Eur J Org Chem, 2003:3 (2003), 492
Yu. V. Tomilov, I. V. Kostyuchenko, G. P. Okonnishnikova, E. V. Shulishov, E. A. Yagodkin, O. M. Nefedov, “Reactions of spirocyclopropane-containing 1- and 2-pyrazolines with electrophilic reagents”, Russ Chem Bull, 49:3 (2000), 472
Yu. V. Tomilov, I. V. Kostyuchenko, E. V. Shulishov, B. B. Averkiev, M. Yu. Antipin, O. M. Nefedov, “Formation and thermal decomposition of adducts of phthalimidonitrene with spiro(1-pyrazolinecyclopropanes)”, Russ Chem Bull, 48:7 (1999), 1316
Yu. V. Tomilov, E. V. Shulishov, G. P. Okonnishnikova, O. M. Nefedov, “The first example of the generation and trapping of diazospiropentane by unsaturated compounds”, Mendeleev Commun., 7:5 (1997), 200–201
Yu. V. Tomilov, G. P. Okonnishnikova, E. V. Shulishov, O. M. Nefedov, “Acylation of spiro(1-pyrazoline-3,1?-cyclopropanes) to form 1-acyl-3-(2-chloroethyl)-2-pyrazolines and transformation of bicyclic 2-pyrazolines into 1,4,5,6-tetrahydropyridazines”, Russ Chem Bull, 44:11 (1995), 2114
YU. V. TOMILOV, G. P. OKONNISHNIKOVA, E. V. SHULISHOV, O. M. NEFEDOV, “ChemInform Abstract: Electrophilic 1,5‐Addition of Acyl Chlorides to Conjugated Azocyclopropanes.”, ChemInform, 25:52 (1994)
Contact us: