Abstract
A novel skeletal rearrangement in the Ritter reaction was examined which conveniently generated p-menthane diamides from turpentine. A probable reaction mechanism was proposed based on employing thermodynamic analysis. All the products were purified and characterised by 1H NMR, IR, X-ray crystallography and ESI+-MS.
References
1.
Polshettiwar V.
, and
Varma R.S.
, Tetrahedron Lett. , 2008 , 49 , 2661 .
2.
Lundberg H.
,
Tinnis F.
,
Selander N.
, and
Adolfsson H.
, Chem. Soc. Rev. , 2014 , 43 , 2714 .
3.
Mina S.
,
Fereshteh G.
,
Mohammad M.
,
Pouria S.
,
Ali A.
,
Abbas S.
, and
Alireza F.
, J. Chem. Res. , 2014 , 38 , 131 .
4.
Meng Q.
,
Luo H.
,
Chen Y.
,
Wang T.
, and
Yao Q.
, Bioorg. Med. Chem. Lett. , 2009 , 19 , 5372 .
5.
Xu K.
,
Zhang Y.
,
Luo J.
,
Chen S.
, and
Wang Y.
, J. Chem. Res. , 2010 , 34 , 354 .
6.
Antoszczak M.
,
Maj E.
,
Stefańska J.
,
Wietrzyk J.
,
Janczak J.
,
Brzezinski B.
, and
Huczyński A.
, Bioorg. Med. Chem. , 2014 , 24 , 1724 .
7.
Jiang D.
,
He T.
,
Ma L.
, and
Wang Z.
, RSC Adv. , 2014 , 4 , 64936 .
8.
Bahareh S.
,
Ebrahim F.
, and
Alireza H.
, J. Chem. Res. , 2012 , 36 , 539 .
9.
Zhang Q.
,
Geng A.
,
Liu Z.
,
Shi Y.
, and
Sun D.
, J. Chem. Crystallogr. , 2012 , 42 , 1124 .
10.
Mesquita L.M.M.
,
Pinto R.M.A.
,
Salvador J.A.R.
,
Clark J.H.
, and
Budarin V.L.
, Catal. Commun. , 2015 , 69 , 170 .
11.
Guérinot A.
,
Reymond S.
, and
Cossy J.
, Eur. J. Org. Chem. , 2012 , 1 , 19 .
12.
Yasuda K.
, and
Obora Y.
, J. Organomet. Chem. , 2015 , 775 , 33 .
13.
Gu Y.
,
Zhao Z.
,
Song J.
,
Li D.
,
Wang J.
,
Lu Y.
, and
Bi L.
, Adv. Mater. Res. , 2013 , 634-638 , 424 .
14.
Sekine N.
, and
Shibutani S.
, J. Wood. Sci. , 2013 , 59 , 229 .
15.
Kovals'skaya S.S.
,
Kozlov N.G.
, and
Tikhonova T.S.
, Chem. Nat. Compd. , 1989 , 25 , 552 .
16.
Li L.
,
Liu Y.
,
Yu S.
,
Liu S.
,
Xie C.
, and
Liu F.
, Res. Chem. Intermed. , 2015 , 41 , 2407 .
17.
Reddy B.V.S.
,
Reddy N.S.
,
Madan C.
, and
Yadav J.S.
, Tetrahedron Lett. , 2010 , 51 , 4827 .
18.
Müller P.
,
Herbst-Irmer R.
,
Spek A.L.
,
Schneider T.R.
,
Sawaya M.R.
, Crystal Structure Refinement: A Crystallographer's Guide to SHELXL , Oxford University Press , Oxford , 2006 .
19.
Sheldrick G.M.
, Acta Crystallogr. A , 2015 , 71 , 3 .
20.
Sheldrick G.M.
, Acta Crystallogr. C , 2015 , 71 , 3 .
21.
Dolomanov O.V.
,
Bourhis L.J.
,
Gildea R.J.
,
Howard J.A.K.
,
Puschmann H.
, J. Appl. Cryst. , 2009 , 42 , 339 .