Regioselectivity of nucleophilic substitution of the nitro group in 2,4,6-trinitrobenzamide

Regioselectivity of nucleophilic substitution of the nitro group in 2,4,6-trinitrobenzamide Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2000, Volume: 41, Number: 25, Pages: 4973-4975 Pages count : 3 DOI: 10.1016/s0040-4039(00)00750-4

Authors

Shkinyova Tatyana K ¹ , Dalinger Igor L ¹ , Molotov Sergei I ¹ , Shevelev Svyatoslav A ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation

Under the action of anionic nucleophiles RO− (R=Ph, HCF2CF2CH2), R′S− (R′=Ph, PhCH2, C2H5OC(O)CH2), N3− on 2,4,6-trinitrobenzamide in MeCN or DMF, the ortho-nitro group is substituted with high selectivity. Intramolecular cyclisation involving ortho-positioned fragments SX and -CONH2 (XC2H5OC(O)CH2, Cl) has been achieved with the formation of 2-ethoxycarbonyl-3-hydroxy-4,6-dinitrobenzo[b]thiophene and 4,6-dinitro-2H-benzo[b]isothiazol-3-one correspondingly.

Shkinyova T.K. , Dalinger I.L. , Molotov S.I. , Shevelev S.A.
Regioselectivity of nucleophilic substitution of the nitro group in 2,4,6-trinitrobenzamide
Tetrahedron Letters. 2000. V.41. N25. P.4973-4975. DOI: 10.1016/s0040-4039(00)00750-4 WOS Scopus OpenAlex

≡ Web of science:	WOS:000087794300031
≡ Scopus:	2-s2.0-0034686332
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