Sustainable synthetic approaches using [C16Im][Oxa] as a flexible organocatalyst and DFT…
1
,4-Bis(2H-benzo[e][1,3]oxazin-3(4H)-yl)benzene (2f)
Yield: 96%; yellow crystalline solid; m.p.: 178–179 °C
Acknowledgements This work was financially supported by the
Uluda g˘ University Scientific Research Projects Unit (KUAP(F)-2015/
1
5).
(
Ref. [54] 180 °C).
0
0
4
,4 -Bis(2H-benzo[e][1,3]oxazin-3(4H)-yl)-1,1 -biphenyl
(
2g, C H N O )
2
References
8 24 2 2
Yield: 95%; bright yellowish crystals; m.p.: 227–228 °C
MeOH); IR (ATR): mꢀ = 3045, 2921, 2851, 1608, 1590,
1
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(
1
1
7
505, 1493, 1456, 1408, 1370, 1333, 1274, 1254, 1214,
164, 1150, 1120, 1080, 1046, 1026, 930, 871, 804, 745,
-
1
1
12, 669, 588 cm
;
H NMR (400 MHz, CDCl3):
d = 6.57–6.52 (m, 4H, Ar), 6.29–6.22 (m, 6H, Ar),
.17–6.12 (m, 2H, Ar), 6.05–5.99 (m, 2H, Ar), 5.96–5.91
m, 2H, Ar), 4.50 (s, 4H, 2x–NCH O–), 3.77 (s, 4H, 2x
6
3
. Hoffmann RW (2000) Angew Chem Int Ed 39:2054
(
2
4. Keisuke A, Seijiro M (2009) Org Lett 11:1757
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1
3
ArCH N–) ppm; C NMR (100 MHz, CDCl ): d = 154.3,
2
3
6
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1
47.2, 133.9, 127.9, 127.4, 126.8, 120.8, 118.5, 116.9,
7
9.4, 50.4 ppm.
7
(
2010) Chem Commun 46:4091
3
-Dodecyl-3,4-dihydro-2H-benzo[e][1,3]oxazine (2h)
Yield: 96%; bright white crystals; m.p.: 35–36 °C (Ref.
61] 60 °C).
8
9
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[
1
1
3
-Tetradecyl-3,4-dihydro-2H-benzo[e][1,3]oxazine
(
2i, C H NO)
2
2 37
1
1
2. Reddy MV, Dindulkar SD, Jeong YT (2011) Tetrahedron Lett
2:4764
3. Singh P, Kumari K, Dubey M, Vishvakarma VK, Mehrotra GK,
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Yield: 95%; bright white crystals; m.p.: 44–45 °C
MeOH); IR (ATR): mꢀ = 3076, 3043, 2914, 2849, 1607,
5
(
1
1
7
583, 1488, 1457, 1378, 1346, 1334, 1291, 1269, 1223,
172, 1145, 1109, 1083, 1033, 978, 923, 866, 839, 808,
-1 1
51, 718, 705, 588 cm ; H NMR (400 MHz, CDCl ):
14. Das S, Santra S, Mondal P, Majee A, Hajra A (2016) Synthesis
8:1269
1
4
3
5. Savanur HM, Kalkhambkar RG, Aridoss G, Laali KK (2016)
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J Solid State Chem 241:86
d = 7.11 (t, J = 7.2 Hz, 1H, Ar), 6.96 (d, J = 7.2 Hz, 1H,
Ar), 6.86 (t, J = 7.2 Hz, 1H, Ar), 6.77 (d, J = 8 Hz, 1H,
Ar), 4.87 (s, 2H, –NCH O–), 3.99 (s, 2H, ArCH N–), 2.73
1
2
2
1
1
7. Rao GBD, Anjaneyulu B, Kaushik MP (2014) RSC Adv 4:43321
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(
t, J = 7.2 Hz, 2H, ring-NCH CH –), 1.55 (quin,
2 2
J = 7.2 Hz, 2H, ring-NCH CH CH –), 1.31–1.25 (m,
2
2
2
2
1
2H, 11x–CH –), 0.88 (t, J = 7.2 Hz, 3H, –CH ) ppm;
2 3
19. Harikrishnan PS, Rajesh SM, Perumal S, Almansour AI (2013)
Tetrahedron Lett 54:1076
2
3
C NMR (100 MHz, CDCl ): d = 154.2, 127.6, 127.5,
3
0. Alvim HGO, Lima TB, de Oliveira AL, de Oliveira HCB, Silva
FM, Gozzo FC, Souza RY, da Silva WA, Neto BAD (2014) J Org
Chem 79:3383
1
2
20.4, 120.3, 116.3, 82.4, 5.36, 50.2, 31.9, 3 9 29.7, 29.6,
9.5, 29.4, 28.1, 27.2, 22.7, 14.2 ppm.
2
2
1. Oliverio M, Costanzo P, Nardi M, Rivalta I, Procopio A (2014)
ACS Sustain Chem Eng 2:1228
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3
-Hexadecyl-3,4-dihydro-2H-benzo[e][1,3]oxazine
(
2j, C H NO)
24 41
Yield: 97%; bright white crystals; m.p.: 51–52 °C
MeOH); IR (ATR): mꢀ = 3079, 3046, 2914, 2848, 1608,
23. Kudoh R, Sudo A, Endo T (2010) Macromolecules 43:1185
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(
4
3:8933
5. Sawaryn C, Landfester K, Taden A (2011) Macromolecules
4:5650
1
1
7
584, 1488, 1470, 1458, 1380, 1346, 1336, 1299, 1266,
2
228, 1173, 1146, 1111, 1096, 1033, 978, 924, 866, 841,
-
4
1
1
95, 752, 718, 705, 590 cm
;
H NMR (400 MHz,
26. Debache A, Amimour M, Belfaitah A, Rhouati S, Carboni BA
(2008) Tetrahedron Lett 49:6119
CDCl ): d = 7.11 (t, J = 7.2 Hz, 1H, Ar), 6.96 (d,
3
2
7. Zhang H, Zhou Z, Yao Z, Xu F, Shen Q (2009) Tetrahedron Lett
0:1622
8. Kolvari E, Koukabi N, Armandpour O (2014) Tetrahedron 70:1383
J = 7.2 Hz, 1H, Ar), 6.86 (t, J = 7.2 Hz, 1H, Ar), 6.77
5
(
d, J = 8 Hz, 1H, Ar), 4.87 (s, 2H, –NCH O–), 3.99 (s, 2H,
2
2
ArCH N–), 2.73 (t, J = 7.2 Hz, 2H, ring-NCH CH –),
2
29. Ranu BC, Hajra A, Jana U (2000) J Org Chem 65:6270
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rus Sulfur Silicon Relat Elem 179:2259
2
2
1
1
–
1
3
.55 (quin, J = 7.2 Hz, 2H, ring-NCH CH CH –),
2 2 2
.30–1.25 (m, 26H, 13x–CH –), 0.88 (t, J = 7.2 Hz, 3H,
2
3
1. Zumpe FL, Fl u¨ ß M, Schmitz K, Lender A (2007) Tetrahedron
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1
3
CH ) ppm; C NMR (100 MHz, CDCl ): d = 154.2,
3
3
27.6, 127.5, 120.4, 120.3, 116.3, 82.4, 51.4, 50.2, 31.9,
32. Suzuki I, Iwata Y, Takeda K (2008) Tetrahedron Lett 49:3238
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9 29.7, 29.6, 29.5, 29.4, 28.1, 27.3, 22.7, 14.2 ppm.
123