Synthesis and x-ray crystal structure of 1,3,3-trinitroazetidine

Archibald, Thomas; Gilardi, Richard; Baum, Kurt; George, Clifford

doi:10.1021/jo00296a066

Cited by 181 publications

(110 citation statements)

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“…In recent years, several new explosives have been synthesized which are more powerful than most currently used military explosives.1 Among these, 1,3,3-trinitroazetidine (TNAZ) holds promise, being both highly energetic and steam castable (melting point 101 ¡C), and therefore is being considered as a substitute for TNT. 2,3 The evaluation of TNAZ for use as a military explosive requires stability studies which include detailed characterization of intermediates and products associated with thermal decomposition.4 Elucidation of fragmentation pathways from electron impact (EI) mass spectrometry may provide insights into thermal decomposition mechanisms of energetic materials.…”

Section: Introductionmentioning

confidence: 99%

Mass Spectral Fragmentation Pathways in 1,3,3-Trinitroazetidine

et al. 1997

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Section: Introductionmentioning

confidence: 99%

Mass Spectral Fragmentation Pathways in 1,3,3-Trinitroazetidine

et al. 1997

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“…The C-N bond of TTTO is found to be longer than the normal C-N single bond reported as 1.49 Å, 39 while the difference is not significant. Lengths of N-NO 2 bonds in TTTO are all 1.424 Å, longer than the usual N-N bond lengths (1.35-1.40 Å) in nitramines 40 because of the electron withdrawing inductive effect of the nitro group. It is proposed that the C-C bonds in TTTO correspond to C1-C9 and C2-C8 bonds, which are all 1.603 Å.…”

Section: Molecular Geometry and Crystal Structurementioning

confidence: 76%

A Theoretical investigation of a potential high energy density compound 3,6,7,8-tetranitro-3,6,7,8-tetraaza-tricyclo[3.1.1.1(2,4)]octane

Zhao¹,

Lu²

2013

Quím. Nova

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Recebido em 3/5/12; aceito em 30/10/12; publicado na web em 6/3/13The B3LYP/6-31G (d) density functional theory (DFT) method was used to study molecular geometry, electronic structure, infrared spectrum (IR) and thermodynamic properties. Heat of formation (HOF) and calculated density were estimated to evaluate detonation properties using Kamlet-Jacobs equations. Thermal stability of 3,6,7,8-tetranitro-3,6,7,8-tetraaza-tricyclo . Both detonation velocity of 9.79 km s -1 and detonation pressure of 44.22 GPa performed similarly to CL-20. According to the quantitative standards of energetics and stability, TTTO essentially satisfies this requirement as a high energy density compound (HEDC).

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“…[1][2][3][4][5][6][7][8][9][10] Specifically, the synthetic utility of ABB (3), which must be useful for the preparation of various 1,3-disubstituted and 3-monosubstituted azetidines, 1,9,10) has scarcely reported because of its synthetic difficulty due to the remarkably strained structure. These azetidine moieties have often been found in many natural products 11) and biologically active compounds such as carbapenems 1) and new quinolone antibiotics.12-15) 1,3,3-Trinitroazetidine (TNAZ), 16,17) an insensitive high explosive, was also synthesized by using ABB (3). In recent years, we established an efficient method for synthesis of ABB (3) starting from allylamine (1) via 2,3-dibromopropylamine hydrobromide (2), and reported its application to the synthesis of several azetidine derivatives, as shown in Chart 1.…”

mentioning

confidence: 99%

“…12-15) 1,3,3-Trinitroazetidine (TNAZ), 16,17) an insensitive high explosive, was also synthesized by using ABB (3). In recent years, we established an efficient method for synthesis of ABB (3) starting from allylamine (1) via 2,3-dibromopropylamine hydrobromide (2), and reported its application to the synthesis of several azetidine derivatives, as shown in Chart 1.…”

mentioning

confidence: 99%

“…These azetidine moieties have often been found in many natural products 11) and biologically active compounds such as carbapenems 1) and new quinolone antibiotics. [12][13][14][15] 1,3,3-Trinitroazetidine (TNAZ), 16,17) an insensitive high explosive, was also synthesized by using ABB (3). In recent years, we established an efficient method for synthesis of ABB (3) starting from allylamine (1) via 2,3-dibromopropylamine hydrobromide (2), and reported its application to the synthesis of several azetidine derivatives, as shown in Chart 1.…”

mentioning

confidence: 99%

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Synthesis of New Quinolone Antibiotics Utilizing Azetidine Derivatives Obtained from 1-Azabicyclo[1.1.0]butane

Ikee

Hashimoto

Kamino

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Although 1-azabicyclo[1.1.0]butane (ABB, 3) proved to be the unique molecule bearing the highly strained bicyclic structure, little attention has been paid to the unusual ring system. [1][2][3][4][5][6][7][8][9][10] Specifically, the synthetic utility of ABB (3), which must be useful for the preparation of various 1,3-disubstituted and 3-monosubstituted azetidines, 1,9,10) has scarcely reported because of its synthetic difficulty due to the remarkably strained structure. These azetidine moieties have often been found in many natural products 11) and biologically active compounds such as carbapenems 1) and new quinolone antibiotics.12-15) 1,3,3-Trinitroazetidine (TNAZ), 16,17) an insensitive high explosive, was also synthesized by using ABB (3). In recent years, we established an efficient method for synthesis of ABB (3) starting from allylamine (1) via 2,3-dibromopropylamine hydrobromide (2), and reported its application to the synthesis of several azetidine derivatives, as shown in Chart 1. 9) We also reported a practical synthesis of 1-(1,3-thiazolin-2-yl)azetidine-3-thiol as the fascinating pendant moiety of a new oral 1b-methylcarbapenem antibiotic, L-084 by starting from ABB (3).1) This expeditious construction method for 3-monosubstituted azetidine derivatives employing ABB (3) seemed to be useful also for developing new quinolone antibiotics.Fluoroquinolones have been developed and are widely used clinically. This is because they have potent, a broad spectrum of antibacterial activities, and few side effects. [18][19][20][21][22] However, increasingly multidrug-resistant pathogens, especially methicillin-resistant Staphylococcus aureus (MRSA), have become a serious problem particularly during the last decade.23) The resistance levels to quinolones are as yet relatively low but are steadily increasing.24) Therefore new antibacterial agents have become increasingly urgent. This prompted us to develop new quinolones utilizing the azetidine derivatives, in which the C7 substituents of fluoroquinolone carboxylic acids play important antibacterial roles.18-22) Previously, we communicated synthesis and antibacterial activities of new quinolone derivatives utilizing ABB (3). 10)We now describe, in detail, a convenient method of synthesizing several 3-sulfenyl-and 3-aminoazetidine derivatives utilizing ABB (3), and we discuss the synthesis and antibacterial activities of new quinolone antibiotics incorporating these azetidine derivatives to the C7 position. Although several examples of 7-azetidinylquinolones have been reported, [12][13][14][15] there have been not many prominent quinolone antibiotics bearing the azetidinyl substituent groups thus far. We envisaged that the introduction of azetidine derivatives onto the C7 position of the quinolone nucleus might enhance their antibacterial activities against MRSA. Results and DiscussionA tetrahydrofuran (THF) solution of ABB (3), obtained by treatment of 2,3-dibromopropylamine hydrobromide (2) with n-BuLi at Ϫ78°C in THF followed by codistillation with THF, 1) was...

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Synthesis and x-ray crystal structure of 1,3,3-trinitroazetidine

Cited by 181 publications

References 1 publication

Mass Spectral Fragmentation Pathways in 1,3,3-Trinitroazetidine

Mass Spectral Fragmentation Pathways in 1,3,3-Trinitroazetidine

A Theoretical investigation of a potential high energy density compound 3,6,7,8-tetranitro-3,6,7,8-tetraaza-tricyclo[3.1.1.1(2,4)]octane

Synthesis of New Quinolone Antibiotics Utilizing Azetidine Derivatives Obtained from 1-Azabicyclo[1.1.0]butane

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