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1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information Domino reaction of cyclic sulfamidate imines with Morita-Baylis-Hillman acetates promoted by DABCO: a metal-free approach to functionalized nicotinic acid derivatives Debashis Majee, Soumen Biswas, Shaikh M. Mobin and Sampak Samanta* Discipline of Chemistry, Indian Institute of Technology Indore, Simrol, , India S1
2 Crystallographic data: Single crystal X-ray structural of 3ai was collected at 150(2) K using graphite monochromated Mo Kα radiation (λα = Å). The strategy for the Data collection was evaluated by using the CrysAlisPro CCD software. The data were collected by the standard 'phi-omega scan techniques, and were scaled and reduced using CrysAlisPro RED software. The structure was solved by direct methods using SHELXS-97, and refined by full matrix leastsquares with SHELXL-97, refining on F2. The positions of all the atoms were obtained by direct methods. All non-hydrogen atoms were refined anisotropically. The remaining hydrogen atoms were placed in geometrically constrained positions, and refined with isotropic temperature factors, generally 1.2Ueq of their parent atoms. The crystal data are summarized in Table 1. The CCDC number of 3ai ( ) can be obtained free of charge via (or from the Cambridge Crystallographic Data Centre,12 union Road, Cambridge CB21 EZ, UK; Fax: (+44) ; or deposit@ccdc.cam.ac.uk). Figure 1. ORTEP diagram of compound 3ai (CCDC ), thermal ellipsoids drawn at the 50% probability level. S2
3 Table 1. Crystal data for compound 3ai. Compound 3ai Empirical formula C20 H16 2 O4 Formula weight Temperatute 293(2) K Wave length (Å ) A Crystal system, space group Triclinic, P-1 a (Å) b (Å) c (Å) α ( ) β ( ) γ ( ) a =8.1889(3) A b = (5) A c = (4) A alpha = (4) deg. beta = (3) deg. gamma = (3) deg Volume (Å 3 ) (6) A^3 Z, Calculated density (mg/m 3 ) 2, Mg/m^3 Absorption coefficient (mm -1 ) mm^-1 F(000) 364 Crystal size (mm) x x mm Ө range (deg) to deg. Limiting indices -12<=h<=12, -15<=k<=15, -15<=l<=16 Reflections collected / unique / 5548 [R(int) = ] Completeness to Ө = % Max. and min. transmission and Absorption correction Semi-empirical from equivalents Refined method Full-matrix least-squares on F^2 Data / restrains / parameters 5548 / 0 / 236 Goodness-of-fit on F^ Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole (e.a -3 ) and e.a^-3 CCDC S3
4 O O S O dr = 3:1 (intermediate 5) O O S O dr = 3:1 (intermediate 5) S4
5 Boc compound Boc compound 8 S5
6 MeO OBn ac MeO OBn ac S6
7 F 3ad F 3ad S7
8 Br 3af Br 3af S8
9 CF ag CF ag S9
10 C 3ah C Chloroform-d 3ah S10
11 Chloroform-d O 2 3ai Chloroform-d O 2 3ai S11
12 Chloroform-d O 2 CO 2 Me 3aj Chloroform-d O 2 CO 2 Me 3aj S12
13 Chloroform-d CO 2Et 3ak Chloroform-d CO 2Et 3ak S13
14 Me 3ba Me 3ba S14
15 F Me 3bd F Me 3bd S15
16 Cl Me 3be Cl Me be S16
17 Br Me 3bf Br Me 3bf S17
18 CF 3 Me 3bg CF Me 3bg S18
19 C Me 3bh Chloroform-d C Me 3bh S19
20 Chloroform-d Chloroform-d O 2 CO 2 Me Me 3bj Chloroform-d O 2 CO 2 Me Me 3bj S20
21 F MeO 3cd F MeO 3cd S21
22 CF MeO 3cg CF 3 MeO 3cg S22
23 Chloroform-d O 2 MeO 3ci Chloroform-d O 2 MeO 3ci S23
24 Chloroform-d O 2 CO 2 Me MeO 3cj O 2 Chloroform-d CO 2 Me MeO 3cj S24
25 CF 3 OMe OMe 3dg CF 3 OMe dg OMe S25
26 F 3ea F 3ea S26
27 Me F 3eb Me F 3eb S27
28 CF F 3eg CF 3 F 3eg S28
29 OBn OMe F 3ec OBn OMe F ec S29
30 Cl 3fa Cl 3fa S30
31 Chloroform-d C Cl 3fh Chloroform-d C Cl 3fh S31
32 Chloroform-d O 2 Cl CO 2 Me 3gj Chloroform-d O 2 Cl CO 2 Me 3gj S32
33 Br 3ha Br 3ha S33
34 CF Br 3hg CF 3 Br 3hg S34
35 S 3ia S 3ia S35
36 F S 3id F S 3id S36
37 Br S 3if Br S 3if S37
38 CF S 3ig CF S 3ig S38
39 Chloroform-d O 2 S 3ii Chloroform-d O 2 S 3ii S39
40 CF O 3jg CF O 3jg S40
41 OMe am C OMe C am S41
42 OMe MeO C an OMe MeO 3an C S42
43 OBn OMe C ao OBn OMe C 3ao S43
44 F 3ap C F ap C S44
45 Cl aq C Cl aq C S45
46 Br ar C Br C ar S46
47 CF as C CF 3 C as S47
48 OMe Me MeO 3bn C OMe Me MeO 3bn C S48
49 Cl Me 3bq C Cl C Me 3bq S49
50 Br C Me 3br Br C Me br S50
51 C MeO 3cl C MeO 3cl S51
52 Cl 3gl C Cl C gl S52
53 C Cl 3fl C Cl 3fl S53
54 OMe Br MeO 3hn C OMe MeO C Br 3hn S54
55 Cl Br 3hq C Cl C Br 3hq S55
56 CF Br 3hs C CF 3 C Br hs S56
57 S 3il C S 3il C S57
58 OMe MeO C S 3in OMe MeO C S 3in S58
59 Chloroform-d O 2 COMe 3at Chloroform-d O 2 COMe 3at S59
60 C COMe 3au C COMe 3au 200 S60
61 C COMe Me 3bu C COMe Me 3bu 200 S61
62 O 2 COMe MeO 3ct O 2 COMe MeO 3ct 200 S62
63 O F 3et COMe O COMe F et S63
64 C F 3eu COMe C COMe F 3eu S64
65 O 2 COMe Cl 3ft O 2 COMe Cl 3ft 200 S65
66 Chloroform-d O 2 COMe S 3it Chloroform-d O 2 COMe S 3it S66
67 Chloroform-d C COMe S 3iu Chloroform-d C COMe S 3iu S67
68 Chloroform-d Chloroform-d S68
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