Synthesis of [3^n]Cyclophanes and Related Compounds by Alkylation of Tosylmethyl Isocyanide with Bis (bromomethyl) benzenes

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概要

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• Bis (2-isocyano-2-tosylethyl) benzenes (12a, 12b, and 12c), synthesized by the reaction of tosylmethyl isocyanide (7) with bis (bromomethyl) benzenes (11a, 11b, and 11c) in 2 : 1 molar ratio, reacted again with 11a, 11b, and 11c under phase-transfer conditions to form 2,11-diisocyano-2,11-ditosyl[3^2]cyclophanes of ortho, meta, and para types (14,15,and 17), 2,11,20-triisocyano-2,11,20-tritosyl[3^3]paracyclophane (19), and 2,11,20,29-tetratosyl[3^4]cyclophanes of meta and para types (16 and 18). [3^2]Metacyclophane (1), [3^3]paracyclophane (31), and [3^4]meta- and paracyclophanes (32 and 33) could be obtained by hydrolysis and Wolff-Kishner reduction of the above intermediates (15,16,18,and 19). Hydrolysis of 2,11-diisocyano-2,11-ditosyl[3^2]orthocyclophane (14) yielded 5,6,11,12-tetrahydro-dibenz[b, g]-azulen-5-one (30) instead of the corresponding ketone (26). Structural properties of the prepared cyclophanes (15,17,21,23,24,31,and 33) are described on the basis of the proton magnetic resonance (PMR) spectra.

• 社団法人日本薬学会の論文
• 1983-08-25

著者

• 北川 徳治郎

  Faculty of Pharmaceutical Sciences

• 佐々木 秀明

  Faculty Of Pharmaceutical Sciences Kobe-gakuin University

• 北川 徳治郎

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

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