Synthesis of a Strain Molecule, 1-Azabicyclo [1.1.0] butane
نویسندگان
چکیده
منابع مشابه
[Synthesis of a strain molecule, 1-azabicyclo [1.1.0] butane].
1-Azabicyclo [1.1.0] butane (ABB) bearing the highly strained bicyclic structure, which is synthetically useful for the preparation of 3-substituted azetidines, was obtained by the cyclization of 2,3-dibromopropylamine hydrobromide derived from inexpensive allylamine only with organolithium compounds and lithium amides. When other bases were employed, such as potassium, sodium, and magnesium sp...
متن کاملThe First Ring-Expansion of a 1-Azabicyclo[1.1.0]butane to a 1- Azabicyclo[2.1.1]hexane
The reactions of 3-phenyl-1-azabicyclo[1.1.0]butane (4) with dimethyl dicyanofumarate ((E)-8) and dimethyl dicyanomaleate ((Z)-8) lead to the same mixture of cisand trans-4-phenyl-1-azabicyclo[2.1.1]hexane 2,3-dicarboxylates (cis-11 and trans-11, resp.; Scheme 3). This result of a formal cycloaddition to the central C-N bond of 4 is interpreted by a stepwise reaction mechanism via a relatively ...
متن کاملMechanistic considerations for the consecutive cyclization of 2,3-dibromopropylamine hydrobromide giving a strained molecule, 1-azabicyclo[1.1.0]butane.
The effective formation of 1-azabicyclo[1.1.0]butane (2) by treatment of 2,3-dibromopropylamine hydrobromide (1) with n-BuLi could be understood considering a rational reaction pathway via both transition states 10 and 19 based on the intramolecular Br...Li(+) coordination. A similar cyclization pathway starting from N-benzyl-3-bromopropylamine hydrochloride (17) to afford N-benzylazetidine (18...
متن کاملCoherent dynamics in a butane molecule.
We have simulated by molecular dynamics a single molecule of butane in a thermal bath at different temperatures. We have found that the collective degrees of freedom of the essential dynamics are endowed with quite different degrees of coherence, and that those subject to the largest fluctuations are also the most coherent, that is, the least chaotic. We suggest that this pattern may be charact...
متن کاملMicrowave-assisted solvent-free synthesis and antibacterial evaluation of 1-azabicyclo[3.1.0]hexane-3-enes
This work described a simple and efficient method for the synthesis of 1-azabicyclo[3.1.0]hexane-3-ene derivatives. arylidenmalononitriles and hydroxylamine hydrochloride in the presence of NaOH, under microwave irradiation and solvent-free conditions produced the titled compounds in good to excellent yields. Using of simple chemicals, short reaction times, and solvent-free conditions, high yie...
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ژورنال
عنوان ژورنال: YAKUGAKU ZASSHI
سال: 2010
ISSN: 0031-6903,1347-5231
DOI: 10.1248/yakushi.130.1339