ZACHOVÁ, Hana, Stanislav MAN, Marek NEČAS a Milan POTÁČEK. Fused tetracyclic heterocycles by thermally initiated intramolecular criss-cross cycloaddition of 3-substituted homoallenylazines. European Journal of Organic Chemistry. Weinheim, Germany: WILEY-VCH, 2005, roč. 2005, č. 12, s. 2548-2557. ISSN 1434-193X. |
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@article{572361, author = {Zachová, Hana and Man, Stanislav and Nečas, Marek and Potáček, Milan}, article_location = {Weinheim, Germany}, article_number = {12}, keywords = {allenes; cycloaddition; nitrogen heterocycles; sigmatropic rearrangement; polycycles}, language = {eng}, issn = {1434-193X}, journal = {European Journal of Organic Chemistry}, title = {Fused tetracyclic heterocycles by thermally initiated intramolecular criss-cross cycloaddition of 3-substituted homoallenylazines}, volume = {2005}, year = {2005} }
TY - JOUR ID - 572361 AU - Zachová, Hana - Man, Stanislav - Nečas, Marek - Potáček, Milan PY - 2005 TI - Fused tetracyclic heterocycles by thermally initiated intramolecular criss-cross cycloaddition of 3-substituted homoallenylazines JF - European Journal of Organic Chemistry VL - 2005 IS - 12 SP - 2548-2557 EP - 2548-2557 PB - WILEY-VCH SN - 1434193X KW - allenes KW - cycloaddition KW - nitrogen heterocycles KW - sigmatropic rearrangement KW - polycycles N2 - A thermally initiated intramolecular criss-cross cycloaddition of 3-substituted symmetrical homoallenyl azines (5) was searched. Their cyclization led to interesting new fused heterocyclic systems consisting of four five-membered rings with two nitrogen heteroatoms (6). The preparation of azines was based on application of homoallenylaldehydes (4) in reaction with hydrazine. The homoallenylaldehydes (4) were prepared by Claisen rearrangement of new N,N-disubstituted 4-[(2-methylprop-1-en-1-yl)oxy]but-2-yn)-1-amines (3a-f) prepared by Mannich reaction from 2-methylprop-1-en-1-yl prop-2-yn-1-yl ether (2). The success in the reaction was based on improved solventless procedure of 1-chloro-2-methylpropyl prop-2-yn-1-yl ether (1) synthesis and its conversion to fully isolable 2-methylprop-1-en-1-yl prop-2-yn-1-yl ether (2) in high yield. ER -
ZACHOVÁ, Hana, Stanislav MAN, Marek NEČAS a Milan POTÁČEK. Fused tetracyclic heterocycles by thermally initiated intramolecular criss-cross cycloaddition of 3-substituted homoallenylazines. \textit{European Journal of Organic Chemistry}. Weinheim, Germany: WILEY-VCH, 2005, roč.~2005, č.~12, s.~2548-2557. ISSN~1434-193X.
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