Abstract:
The easy transformation of 2-(1-alkoxyethoxy)-N-(1-methylethylidene)-1-(methylsulfanyl)-1,3-butadien-1-amines (2-aza-1,3,5-trienes) into 3-(1-alkoxyethoxy)-7-methyl-2-(methylsulfanyl)-4,5-dihydro-3H-azepines and 6-(1-alkoxyethoxy)-2-methyl-3H-azepines has been found to proceed under the action of ButOK in THF–DMSO or THF; the mild acidic hydrolysis of 4,5-dihydro-3H-azepines gives hydroxy derivatives.
Citation:
N. A. Nedolya, O. A. Tarasova, A. I. Albanov, O. G. Volostnykh, L. Brandsma, B. A. Trofimov, “A new approach to densely functionalised azepines and dihydroazepines”, Mendeleev Commun., 18:3 (2008), 164–166
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https://www.mathnet.ru/eng/mendc/v18/i3/p164
This publication is cited in the following 17 articles:
N. A Nedolya, “Acetylenic and allenic carbanions in the reaction with heterocumulenes: a simple way to fundamental heterocycles”, Žurnal organičeskoj himii, 59:10 (2023), 1319
N. A. Nedolya, “Reactions of Acetylenic and Allenic Carbanions with Heterocumulenes: A Straightforward Route to Fundamental Heterocycles”, Russ J Org Chem, 59:10 (2023), 1676
O. A. Tarasova, N. A. Nedolya, A. I. Albanov, “One-Pot Synthesis of 1-(1-Alkoxyethoxy)allenes”, Russ J Org Chem, 54:12 (2018), 1831
V. A. Shagun, N. A. Nedolya, “Heterocumulenes reactions with organometallic reagents XXIII. Quantum-chemical study of structural transformations of (propargylsulfanyl)-substituted 2-Aza-1,3,5-triene treated with potassium tert-butoxide”, Russ J Org Chem, 51:8 (2015), 1101
V. A. Shagun, N. A. Nedolya, “Reactions of heterocumulenes with organometallic reagents: XXII. Quantum chemical study of structural transformations of benzylsulfanyl-substituted 2-aza-1,3,5-triene by the action of superbases. Concurrent formation of 4,5-dihydro-3H-azepine and 4,5-dihydro-1,3-thiazole”, Russ J Org Chem, 51:4 (2015), 504
Nina A. Nedolya, Ol'ga A. Tarasova, Alexander I. Albanov, Boris A. Trofimov, “Structural reorganization of (allyl-, benzyl-, and propargylsulfanyl)-substituted 2-aza-1,3,5-trienes in t-BuOK/THF/DMSO: access to rare functionalized 2-thiazolines”, Tetrahedron Letters, 55:15 (2014), 2495
N. A. Nedolya, O. A. Tarasova, A. I. Albanov, B. A. Trofimov, “Rearrangement of benzylsulfanyl-substituted 2-aza-1,3,5-triene into 5-phenyl-4,5-dihydro-1,3-thiazole in the t-BuOK-THF-DMSO system”, Russ J Org Chem, 49:10 (2013), 1491
N. A. Nedolya, B. A. Trofimov, “[1,7]-Electrocyclization reactions in the synthesis of azepine derivatives”, Chem Heterocycl Comp, 49:1 (2013), 152
N. A. Nedolya, O. G. Volostnykh, O. A. Tarasova, A. I. Albanov, B. A. Trofimov, “New transformations of 2-Aza-1,3,5-trienes by the action of t-BuOK-THF-DMSO”, Russ J Org Chem, 47:1 (2011), 141
Nina A. Nedolya, Ol'ga A. Tarasova, Ol'ga G. Volostnykh, Alexander I. Albanov, Boris A. Trofimov, “Simultaneous synthesis of 4,5-dihydro-3H-azepines and 3H-azepines, bearing alkoxy and alkylsulfanyl substituents, through metallation of 2-aza-1,3,5-trienes by t-BuOK”, Journal of Organometallic Chemistry, 696:21 (2011), 3359
V. A. Shagun, N. A. Nedolya, O. A. Tarasova, O. G. Volostnykh, O. N. Kazheva, A. N. Chekhlov, G. G. Aleksandrov, O. A. D'yachenko, “Reactions of heterocumulenes with organometallic reagents: XVI. Quantum-chemical study on the mechanisms of formation of homo- and heteroannular azacycloheptadienes in reactions of 2-aza-1,3,5-trienes with potassium tert-butoxide”, Russ J Org Chem, 46:12 (2010), 1848
O. A. Tarasova, N. A. Nedolya, A. I. Albanov, B. A. Trofimov, “New approach to N-vinylpyrroles”, Russ J Org Chem, 46:5 (2010), 773
L. V. Klyba, N. A. Nedolya, O. A. Tarasova, E. R. Zhanchipova, O. G. Volostnykh, “Mass spectra of new heterocycles: IX. Main fragmentaion laws of 7-methyl-2-(methylsulfanyl)-3-(1-ethoxyethoxy)-4,5-dihydro-3H-azepine and its structural isomers (2,3-dihydropyridine, pyrrole, thiophene) under electron impact”, Russ J Org Chem, 46:2 (2010), 218
L. V. Klyba, N. A. Nedolya, O. A. Tarasova, E. R. Zhanchipova, O. G. Volostnykh, “Mass spectra of new heterocycles: VIII. Fragmentation of 6-alkoxy- and 6-aryl(hetaryl)-3H-azepines under electron impact”, Russ J Org Chem, 45:4 (2009), 596
Nina A. Nedolya, Ol'ga A. Tarasova, Alexander I. Albanov, Ol'ga G. Volostnykh, Lambert Brandsma, Boris A. Trofimov, “ChemInform Abstract: A New Approach to Densely Functionalized Azepines and Dihydroazepines.”, ChemInform, 39:44 (2008)
N. A. Nedolya, “Chemistry of heterocyclic compounds at the A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, over 50 years (Review)”, Chem Heterocycl Comp, 44:10 (2008), 1165
N. A. Nedolya, O. A. Tarasova, O. G. Volostnykh, A. I. Albanov, “New approach to the formation of azepine ring: Synthesis of 2-methyl-6-(5-methyl-2-thienyl)-3H-azepine from 2-methyl-5-propargylthiophene and isothiocyanate”, Chem Heterocycl Comp, 44:9 (2008), 1113
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